# Electronic Supplementary Material (ESI) for Materials Horizons.
# 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_wym-h4
_database_code_depnum_ccdc_archive 'CCDC 2248788'
loop_
_audit_author_name
_audit_author_address
'Yimin Wu'
;Sichuan University
China
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2019-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H11 N O2'
_chemical_formula_sum            'C20 H11 N O2'
_chemical_formula_weight         297.30
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.1959(6)
_cell_length_b                   13.4702(10)
_cell_length_c                   10.7519(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.216(5)
_cell_angle_gamma                90
_cell_volume                     1331.54(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1623
_cell_measurement_temperature    292.26(10)
_cell_measurement_theta_max      71.4210
_cell_measurement_theta_min      5.8290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3083
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.736
_diffrn_reflns_theta_min         5.827
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.26(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.11    --  -36.42  57.00  90.00   84
  2  ω    -55.00  33.00   1.00    1.11    --  -36.42  38.00-120.00   88
  3  ω     23.00  90.00   1.00    1.11    --   36.42-125.00-120.00   67
  4  ω     20.00 104.00   1.00    1.11    --   36.42  57.00 150.00   84
  5  ω     37.00 109.00   1.00    4.44    --  106.21 -94.00-120.00   72
  6  ω     36.00 113.00   1.00    4.44    --  106.21-111.00  90.00   77
  7  ω     36.00 113.00   1.00    4.44    --  106.21-111.00 -60.00   77
  8  ω     39.00 124.00   1.00    4.44    --  106.21 -61.00 -90.00   85
  9  ω     89.00 175.00   1.00    4.44    --  106.21  45.00 -30.00   86
 10  ω     88.00 173.00   1.00    4.44    --  106.21  61.00   0.00   85
 11  ω     88.00 173.00   1.00    4.44    --  106.21  61.00-180.00   85
 12  ω     39.00 114.00   1.00    4.44    --  106.21 -61.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1051656000
_diffrn_orient_matrix_UB_12      -0.0877045000
_diffrn_orient_matrix_UB_13      -0.0214002000
_diffrn_orient_matrix_UB_21      -0.1283601000
_diffrn_orient_matrix_UB_22      0.0733064000
_diffrn_orient_matrix_UB_23      -0.0117893000
_diffrn_orient_matrix_UB_31      0.0232534000
_diffrn_orient_matrix_UB_32      0.0070867000
_diffrn_orient_matrix_UB_33      -0.1410337000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1171
_reflns_number_total             1274
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.465
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.179
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.080
_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)+(0.1257P)²+0.0840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1673
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D)
;
_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
O001 O 0.85932(12) 0.30322(10) 0.38296(14) 0.0589(4) Uani 1 1 d . . . . .
N002 N 0.5000 0.44703(12) 0.2500 0.0319(4) Uani 1 2 d S T P . .
C003 C 0.5000 0.34361(14) 0.2500 0.0310(4) Uani 1 2 d S T P . .
C004 C 0.59213(13) 0.49720(10) 0.33642(12) 0.0318(4) Uani 1 1 d . . . . .
C005 C 0.71450(14) 0.44841(11) 0.38603(12) 0.0353(4) Uani 1 1 d . . . . .
C006 C 0.38054(13) 0.29084(12) 0.19987(12) 0.0350(4) Uani 1 1 d . . . . .
C007 C 0.74390(15) 0.34384(12) 0.35653(13) 0.0392(4) Uani 1 1 d . . . . .
C008 C 0.55828(14) 0.59216(11) 0.37960(13) 0.0366(4) Uani 1 1 d . . . . .
H008 H 0.4757 0.6247 0.3492 0.044 Uiso 1 1 calc R . . . .
C009 C 0.80362(15) 0.49680(12) 0.47429(14) 0.0420(4) Uani 1 1 d . . . . .
H009 H 0.8858 0.4646 0.5061 0.050 Uiso 1 1 calc R . . . .
C00A C 0.38210(15) 0.18760(12) 0.20259(13) 0.0418(4) Uani 1 1 d . . . . .
H00A H 0.3018 0.1528 0.1717 0.050 Uiso 1 1 calc R . . . .
C00B C 0.64759(16) 0.63773(12) 0.46760(13) 0.0423(4) Uani 1 1 d . . . . .
H00B H 0.6242 0.7009 0.4959 0.051 Uiso 1 1 calc R . . . .
C00C C 0.77179(17) 0.59075(13) 0.51450(14) 0.0460(5) Uani 1 1 d . . . . .
H00C H 0.8323 0.6226 0.5723 0.055 Uiso 1 1 calc R . . . .
C00D C 0.5000 0.13557(16) 0.2500 0.0456(5) Uani 1 2 d S T P . .
H00D H 0.5000 0.0665 0.2500 0.055 Uiso 1 2 calc RS T P . .


_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 C007 1.2222(18) . ?
N002 C003 1.393(3) . ?
N002 C004 1.4158(15) . ?
N002 C004 1.4158(15) 2_655 ?
C003 C006 1.4062(17) 2_655 ?
C003 C006 1.4061(17) . ?
C004 C005 1.3991(18) . ?
C004 C008 1.398(2) . ?
C005 C007 1.470(2) . ?
C005 C009 1.401(2) . ?
C006 C007 1.4688(19) 2_655 ?
C006 C00A 1.391(2) . ?
C007 C006 1.4688(19) 2_655 ?
C008 H008 0.9300 . ?
C008 C00B 1.383(2) . ?
C009 H009 0.9300 . ?
C009 C00C 1.371(2) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.3794(19) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.391(2) . ?
C00C H00C 0.9300 . ?
C00D C00A 1.3794(19) 2_655 ?
C00D H00D 0.9300 . ?

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
C003 N002 C004 118.51(8) . . ?
C003 N002 C004 118.51(8) . 2_655 ?
C004 N002 C004 122.97(16) . 2_655 ?
N002 C003 C006 120.36(9) . 2_655 ?
N002 C003 C006 120.36(9) . . ?
C006 C003 C006 119.28(19) . 2_655 ?
C005 C004 N002 119.42(13) . . ?
C008 C004 N002 121.35(12) . . ?
C008 C004 C005 119.08(12) . . ?
C004 C005 C007 121.19(12) . . ?
C004 C005 C009 119.59(14) . . ?
C009 C005 C007 118.96(13) . . ?
C003 C006 C007 120.53(15) . 2_655 ?
C00A C006 C003 119.32(13) . . ?
C00A C006 C007 120.14(12) . 2_655 ?
O001 C007 C005 122.79(14) . . ?
O001 C007 C006 122.92(15) . 2_655 ?
C006 C007 C005 114.17(12) 2_655 . ?
C004 C008 H008 120.0 . . ?
C00B C008 C004 119.99(13) . . ?
C00B C008 H008 120.0 . . ?
C005 C009 H009 119.4 . . ?
C00C C009 C005 121.14(14) . . ?
C00C C009 H009 119.4 . . ?
C006 C00A H00A 119.2 . . ?
C00D C00A C006 121.56(13) . . ?
C00D C00A H00A 119.2 . . ?
C008 C00B H00B 119.4 . . ?
C008 C00B C00C 121.14(15) . . ?
C00C C00B H00B 119.4 . . ?
C009 C00C C00B 119.00(13) . . ?
C009 C00C H00C 120.5 . . ?
C00B C00C H00C 120.5 . . ?
C00A C00D C00A 118.93(19) 2_655 . ?
C00A C00D H00D 120.5 2_655 . ?
C00A C00D H00D 120.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-11-14
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.695
####################################################################### 
# 
# 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_mo_wym_h5_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2248789'
loop_
_audit_author_name
_audit_author_address
'Yimin Wu'
;Sichuan University
China
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H13 N O2'
_chemical_formula_sum            'C24 H13 N O2'
_chemical_formula_weight         347.35
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0822(16)
_cell_length_b                   11.0340(19)
_cell_length_c                   11.143(2)
_cell_angle_alpha                61.646(6)
_cell_angle_beta                 69.236(4)
_cell_angle_gamma                83.968(6)
_cell_volume                     815.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6071
_cell_measurement_temperature    308(2)
_cell_measurement_theta_max      27.405
_cell_measurement_theta_min      2.837
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1345 before and 0.0672 after correction.
The Ratio of minimum to maximum transmission is 0.8553.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22848
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.104
_diffrn_ambient_temperature      308.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2789
_reflns_number_total             3742
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.030
_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)+(0.0421P)²+0.1909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C23(H23)
;
_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 0.34579(17) -0.11217(12) 0.76677(12) 0.0597(3) Uani 1 1 d . . . . .
O2 O 0.10512(18) 0.15734(13) 0.13505(12) 0.0661(4) Uani 1 1 d . . . . .
N1 N 0.24446(15) 0.20626(12) 0.42621(11) 0.0354(3) Uani 1 1 d . . . . .
C1 C 0.2540(2) -0.18630(18) 0.4553(2) 0.0599(5) Uani 1 1 d . . . . .
H1 H 0.2607 -0.2730 0.4599 0.072 Uiso 1 1 calc R U . . .
C2 C 0.2199(2) -0.07482(18) 0.34097(19) 0.0536(4) Uani 1 1 d . . . . .
H2 H 0.2012 -0.0874 0.2698 0.064 Uiso 1 1 calc R U . . .
C3 C 0.21315(19) 0.05604(15) 0.33042(15) 0.0417(3) Uani 1 1 d . . . . .
C4 C 0.1652(2) 0.17319(17) 0.21380(15) 0.0447(4) Uani 1 1 d . . . . .
C5 C 0.20440(19) 0.31004(15) 0.19302(14) 0.0398(3) Uani 1 1 d . . . . .
C6 C 0.26066(18) 0.32312(14) 0.29075(13) 0.0349(3) Uani 1 1 d . . . . .
C7 C 0.34289(18) 0.45232(14) 0.25022(14) 0.0362(3) Uani 1 1 d . . . . .
C8 C 0.4399(2) 0.46870(16) 0.32593(15) 0.0413(3) Uani 1 1 d . . . . .
H8 H 0.4524 0.3923 0.4074 0.050 Uiso 1 1 calc R U . . .
C9 C 0.5151(2) 0.59449(17) 0.28147(17) 0.0500(4) Uani 1 1 d . . . . .
H9 H 0.5790 0.6030 0.3323 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4968(2) 0.71151(17) 0.15944(18) 0.0544(4) Uani 1 1 d . . . . .
H10 H 0.5439 0.7978 0.1325 0.065 Uiso 1 1 calc R U . . .
C11 C 0.33492(19) 0.57005(15) 0.12066(14) 0.0403(3) Uani 1 1 d . . . . .
C12 C 0.4108(2) 0.69903(16) 0.08091(17) 0.0495(4) Uani 1 1 d . . . . .
H12 H 0.4016 0.7770 -0.0008 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2572(2) 0.55502(17) 0.03251(15) 0.0471(4) Uani 1 1 d . . . . .
H13 H 0.2455 0.6327 -0.0483 0.057 Uiso 1 1 calc R U . . .
C14 C 0.2000(2) 0.42933(17) 0.06468(15) 0.0472(4) Uani 1 1 d . . . . .
H14 H 0.1570 0.4204 0.0019 0.057 Uiso 1 1 calc R U . . .
C15 C 0.19231(18) 0.21358(14) 0.55836(13) 0.0353(3) Uani 1 1 d . . . . .
C16 C 0.10647(19) 0.32558(15) 0.57165(15) 0.0412(3) Uani 1 1 d . . . . .
H16 H 0.0853 0.3987 0.4921 0.049 Uiso 1 1 calc R U . . .
C17 C 0.0531(2) 0.32791(17) 0.70239(16) 0.0480(4) Uani 1 1 d . . . . .
H17 H -0.0039 0.4030 0.7101 0.058 Uiso 1 1 calc R U . . .
C18 C 0.0827(2) 0.22016(18) 0.82290(16) 0.0515(4) Uani 1 1 d . . . . .
H18 H 0.0475 0.2233 0.9103 0.062 Uiso 1 1 calc R U . . .
C19 C 0.1646(2) 0.10922(17) 0.81134(15) 0.0471(4) Uani 1 1 d . . . . .
H19 H 0.1840 0.0365 0.8920 0.056 Uiso 1 1 calc R U . . .
C20 C 0.21970(18) 0.10308(15) 0.68036(14) 0.0384(3) Uani 1 1 d . . . . .
C21 C 0.28888(19) -0.02358(15) 0.67519(15) 0.0422(4) Uani 1 1 d . . . . .
C22 C 0.27212(19) -0.03956(15) 0.55631(16) 0.0419(3) Uani 1 1 d . . . . .
C23 C 0.2780(2) -0.16867(17) 0.56251(19) 0.0530(4) Uani 1 1 d . . . . .
H23 H 0.2985 -0.2445 0.6405 0.064 Uiso 1 1 calc R U . . .
C24 C 0.24395(18) 0.07496(14) 0.43693(14) 0.0369(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
O1 C21 1.2245(17) . ?
O2 C4 1.2258(18) . ?
N1 C6 1.4159(16) . ?
N1 C15 1.4207(17) . ?
N1 C24 1.3963(18) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(2) . ?
C1 C23 1.377(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(2) . ?
C3 C4 1.472(2) . ?
C3 C24 1.404(2) . ?
C4 C5 1.466(2) . ?
C5 C6 1.3884(19) . ?
C5 C14 1.420(2) . ?
C6 C7 1.433(2) . ?
C7 C8 1.415(2) . ?
C7 C11 1.4293(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.361(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.404(2) . ?
C10 H10 0.9300 . ?
C10 C12 1.354(2) . ?
C11 C12 1.411(2) . ?
C11 C13 1.415(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.345(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(2) . ?
C15 C20 1.4021(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.400(2) . ?
C20 C21 1.469(2) . ?
C21 C22 1.469(2) . ?
C22 C23 1.390(2) . ?
C22 C24 1.406(2) . ?
C23 H23 0.9300 . ?

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
C6 N1 C15 122.89(11) . . ?
C24 N1 C6 118.71(11) . . ?
C24 N1 C15 117.10(11) . . ?
C2 C1 H1 120.2 . . ?
C23 C1 H1 120.2 . . ?
C23 C1 C2 119.69(16) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.02(16) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 121.00(14) . . ?
C2 C3 C24 119.29(14) . . ?
C24 C3 C4 119.64(14) . . ?
O2 C4 C3 122.04(15) . . ?
O2 C4 C5 122.52(15) . . ?
C5 C4 C3 115.34(13) . . ?
C6 C5 C4 120.61(13) . . ?
C6 C5 C14 119.89(14) . . ?
C14 C5 C4 119.25(13) . . ?
N1 C6 C7 120.89(12) . . ?
C5 C6 N1 119.36(13) . . ?
C5 C6 C7 119.66(12) . . ?
C8 C7 C6 123.99(12) . . ?
C8 C7 C11 118.07(13) . . ?
C11 C7 C6 117.84(13) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.04(14) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.49(16) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.9 . . ?
C12 C10 C9 120.17(16) . . ?
C12 C10 H10 119.9 . . ?
C12 C11 C7 118.75(14) . . ?
C12 C11 C13 121.24(13) . . ?
C13 C11 C7 119.97(14) . . ?
C10 C12 C11 121.26(14) . . ?
C10 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C11 C13 H13 119.7 . . ?
C14 C13 C11 120.55(13) . . ?
C14 C13 H13 119.7 . . ?
C5 C14 H14 119.5 . . ?
C13 C14 C5 121.02(14) . . ?
C13 C14 H14 119.5 . . ?
C16 C15 N1 121.44(12) . . ?
C16 C15 C20 119.08(13) . . ?
C20 C15 N1 119.40(13) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.10(13) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.16(15) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.10(14) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.25(14) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C21 120.36(13) . . ?
C19 C20 C15 119.28(14) . . ?
C19 C20 C21 120.07(13) . . ?
O1 C21 C20 123.07(14) . . ?
O1 C21 C22 122.71(15) . . ?
C22 C21 C20 114.08(12) . . ?
C23 C22 C21 120.54(14) . . ?
C23 C22 C24 119.07(15) . . ?
C24 C22 C21 120.36(13) . . ?
C1 C23 C22 121.17(16) . . ?
C1 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
N1 C24 C3 120.53(12) . . ?
N1 C24 C22 119.80(13) . . ?
C3 C24 C22 119.67(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C21 C22 C23 16.2(2) . . . . ?
O1 C21 C22 C24 -165.94(14) . . . . ?
O2 C4 C5 C6 175.48(14) . . . . ?
O2 C4 C5 C14 -10.3(2) . . . . ?
N1 C6 C7 C8 11.4(2) . . . . ?
N1 C6 C7 C11 -172.29(12) . . . . ?
N1 C15 C16 C17 178.18(14) . . . . ?
N1 C15 C20 C19 -178.59(13) . . . . ?
N1 C15 C20 C21 -4.7(2) . . . . ?
C1 C2 C3 C4 -175.93(15) . . . . ?
C1 C2 C3 C24 0.9(2) . . . . ?
C2 C1 C23 C22 -1.3(3) . . . . ?
C2 C3 C4 O2 10.8(2) . . . . ?
C2 C3 C4 C5 -165.72(14) . . . . ?
C2 C3 C24 N1 177.62(13) . . . . ?
C2 C3 C24 C22 -3.2(2) . . . . ?
C3 C4 C5 C6 -8.1(2) . . . . ?
C3 C4 C5 C14 166.19(13) . . . . ?
C4 C3 C24 N1 -5.5(2) . . . . ?
C4 C3 C24 C22 173.63(13) . . . . ?
C4 C5 C6 N1 -13.3(2) . . . . ?
C4 C5 C6 C7 163.32(13) . . . . ?
C4 C5 C14 C13 -171.30(15) . . . . ?
C5 C6 C7 C8 -165.14(13) . . . . ?
C5 C6 C7 C11 11.13(19) . . . . ?
C6 N1 C15 C16 18.3(2) . . . . ?
C6 N1 C15 C20 -164.79(13) . . . . ?
C6 N1 C24 C3 -16.53(19) . . . . ?
C6 N1 C24 C22 164.33(12) . . . . ?
C6 C5 C14 C13 3.0(2) . . . . ?
C6 C7 C8 C9 179.87(14) . . . . ?
C6 C7 C11 C12 178.30(13) . . . . ?
C6 C7 C11 C13 -3.8(2) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C7 C11 C12 C10 2.9(2) . . . . ?
C7 C11 C13 C14 -4.0(2) . . . . ?
C8 C7 C11 C12 -5.2(2) . . . . ?
C8 C7 C11 C13 172.72(13) . . . . ?
C8 C9 C10 C12 -3.0(3) . . . . ?
C9 C10 C12 C11 1.3(3) . . . . ?
C11 C7 C8 C9 3.6(2) . . . . ?
C11 C13 C14 C5 4.5(2) . . . . ?
C12 C11 C13 C14 173.85(15) . . . . ?
C13 C11 C12 C10 -175.04(15) . . . . ?
C14 C5 C6 N1 172.46(13) . . . . ?
C14 C5 C6 C7 -10.9(2) . . . . ?
C15 N1 C6 C5 -140.46(14) . . . . ?
C15 N1 C6 C7 42.94(18) . . . . ?
C15 N1 C24 C3 150.84(13) . . . . ?
C15 N1 C24 C22 -28.30(18) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C15 C20 C21 O1 166.19(14) . . . . ?
C15 C20 C21 C22 -17.96(19) . . . . ?
C16 C15 C20 C19 -1.6(2) . . . . ?
C16 C15 C20 C21 172.25(13) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?
C18 C19 C20 C15 0.8(2) . . . . ?
C18 C19 C20 C21 -173.12(14) . . . . ?
C19 C20 C21 O1 -20.0(2) . . . . ?
C19 C20 C21 C22 155.87(14) . . . . ?
C20 C15 C16 C17 1.3(2) . . . . ?
C20 C21 C22 C23 -159.67(14) . . . . ?
C20 C21 C22 C24 18.19(19) . . . . ?
C21 C22 C23 C1 176.86(15) . . . . ?
C21 C22 C24 N1 4.6(2) . . . . ?
C21 C22 C24 C3 -174.59(13) . . . . ?
C23 C1 C2 C3 1.4(3) . . . . ?
C23 C22 C24 N1 -177.55(13) . . . . ?
C23 C22 C24 C3 3.3(2) . . . . ?
C24 N1 C6 C5 26.14(18) . . . . ?
C24 N1 C6 C7 -150.46(13) . . . . ?
C24 N1 C15 C16 -148.47(14) . . . . ?
C24 N1 C15 C20 28.41(18) . . . . ?
C24 C3 C4 O2 -166.06(14) . . . . ?
C24 C3 C4 C5 17.46(19) . . . . ?
C24 C22 C23 C1 -1.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_wym-h6
_database_code_depnum_ccdc_archive 'CCDC 2248790'
loop_
_audit_author_name
_audit_author_address
'Yimin Wu'
;Sichuan University
China
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2020-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H15 N O2'
_chemical_formula_sum            'C28 H15 N O2'
_chemical_formula_weight         397.41
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.1670(4)
_cell_length_b                   10.9238(4)
_cell_length_c                   11.5354(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.397(3)
_cell_angle_gamma                90
_cell_volume                     1905.56(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2683
_cell_measurement_temperature    293.9(2)
_cell_measurement_theta_max      71.2750
_cell_measurement_theta_min      4.5070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5024
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.360
_diffrn_reflns_theta_min         4.994
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  -2.00   1.00    1.00    --  -34.85 125.00  30.00   88
  2  ω     16.00 103.00   1.00    1.00    --   34.85  57.00 120.00   87
  3  ω     23.00  90.00   1.00    1.00    --   34.85-125.00   0.00   67
  4  ω    -34.00  53.00   1.00    1.00    --   34.85 -57.00-150.00   87
  5  ω     23.00  90.00   1.00    1.00    --   34.85-125.00-120.00   67
  6  ω    -34.00  53.00   1.00    1.00    --   34.85 -57.00-180.00   87
  7  ω     23.00  90.00   1.00    1.00    --   34.85-125.00 -90.00   67
  8  ω     13.00 105.00   1.00    1.00    --   34.85  38.00   0.00   92
  9  ω     87.00 175.00   1.00    1.60    --  106.90  61.00  30.00   88
 10  ω     36.00 113.00   1.00    1.60    --  106.90-111.00-120.00   77
 11  ω     57.00 151.00   1.00    1.60    --  106.90 178.00 -90.00   94
 12  ω     35.00 133.00   1.00    1.60    --  106.90 -30.00  90.00   98
 13  ω     37.00 110.00   1.00    1.60    --  106.90 -94.00   0.00   73
 14  ω     87.00 175.00   1.00    1.60    --  106.90  61.00 -90.00   88
 15  ω    100.00 178.00   1.00    1.60    --  106.90 111.00  30.00   78
 16  ω    130.00 167.00   1.00    1.60    --  106.90 111.00-120.00   37
 17  ω    138.00 169.00   1.00    1.60    --  106.90  77.00  60.00   31
 18  ω    103.00 129.00   1.00    1.60    --  106.90  77.00  60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0083041000
_diffrn_orient_matrix_UB_12      -0.1285581000
_diffrn_orient_matrix_UB_13      -0.0546079000
_diffrn_orient_matrix_UB_21      0.0357139000
_diffrn_orient_matrix_UB_22      -0.0570860000
_diffrn_orient_matrix_UB_23      0.1163499000
_diffrn_orient_matrix_UB_31      -0.0950667000
_diffrn_orient_matrix_UB_32      -0.0101890000
_diffrn_orient_matrix_UB_33      0.0375813000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1645
_reflns_number_total             1823
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.244
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.081
_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)+(0.1039P)²+0.3340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1589
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H)
;
_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
N001 N 0.7500 0.62914(13) 0.5000 0.0351(4) Uani 1 2 d S T P . .
O002 O 0.63163(9) 0.80200(13) 0.75524(11) 0.0738(5) Uani 1 1 d . . . . .
C003 C 0.67883(8) 0.56839(12) 0.54777(11) 0.0353(3) Uani 1 1 d . . . . .
C004 C 0.64555(8) 0.45423(12) 0.50200(11) 0.0368(3) Uani 1 1 d . . . . .
C005 C 0.63896(9) 0.62449(14) 0.63825(12) 0.0439(4) Uani 1 1 d . . . . .
C006 C 0.7500 0.75644(18) 0.5000 0.0417(5) Uani 1 2 d S T P . .
C007 C 0.70358(9) 0.82063(14) 0.58144(13) 0.0506(4) Uani 1 1 d . . . . .
C008 C 0.66892(9) 0.40140(13) 0.39691(12) 0.0416(4) Uani 1 1 d . . . . .
H008 H 0.7073 0.4429 0.3517 0.050 Uiso 1 1 calc R . . . .
C009 C 0.58120(9) 0.39227(14) 0.56451(13) 0.0462(4) Uani 1 1 d . . . . .
C00A C 0.65749(9) 0.75286(15) 0.66799(13) 0.0513(4) Uani 1 1 d . . . . .
C00B C 0.63606(11) 0.29044(14) 0.36071(15) 0.0542(4) Uani 1 1 d . . . . .
H00B H 0.6526 0.2569 0.2915 0.065 Uiso 1 1 calc R . . . .
C00C C 0.57340(10) 0.56113(17) 0.69555(13) 0.0553(5) Uani 1 1 d . . . . .
H00C H 0.5482 0.5982 0.7577 0.066 Uiso 1 1 calc R . . . .
C00D C 0.55001(11) 0.27720(16) 0.52497(16) 0.0600(5) Uani 1 1 d . . . . .
H00D H 0.5097 0.2352 0.5670 0.072 Uiso 1 1 calc R . . . .
C00E C 0.54688(10) 0.44854(18) 0.66191(13) 0.0568(5) Uani 1 1 d . . . . .
H00E H 0.5056 0.4072 0.7029 0.068 Uiso 1 1 calc R . . . .
C00F C 0.70500(13) 0.94835(17) 0.58008(17) 0.0703(6) Uani 1 1 d . . . . .
H00F H 0.6750 0.9915 0.6343 0.084 Uiso 1 1 calc R . . . .
C00G C 0.57735(12) 0.22643(16) 0.42729(17) 0.0632(5) Uani 1 1 d . . . . .
H00G H 0.5574 0.1491 0.4040 0.076 Uiso 1 1 calc R . . . .
C00H C 0.7500 1.0116(2) 0.5000 0.0805(9) Uani 1 2 d S T P . .
H00H H 0.7500 1.0968 0.5000 0.097 Uiso 1 2 calc RS T P . .


_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
N001 C003 1.4144(14) . ?
N001 C003 1.4143(14) 2_656 ?
N001 C006 1.391(2) . ?
O002 C00A 1.2310(18) . ?
C003 C004 1.4310(18) . ?
C003 C005 1.3883(17) . ?
C004 C008 1.4122(18) . ?
C004 C009 1.4277(18) . ?
C005 C00A 1.466(2) . ?
C005 C00C 1.416(2) . ?
C006 C007 1.4041(17) . ?
C006 C007 1.4040(17) 2_656 ?
C007 C00A 1.463(2) . ?
C007 C00F 1.395(2) . ?
C008 H008 0.9300 . ?
C008 C00B 1.364(2) . ?
C009 C00D 1.407(2) . ?
C009 C00E 1.415(2) . ?
C00B H00B 0.9300 . ?
C00B C00G 1.406(2) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.342(2) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.349(3) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00H 1.376(2) . ?
C00G H00G 0.9300 . ?
C00H C00F 1.376(2) 2_656 ?
C00H H00H 0.9300 . ?

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
C003 N001 C003 124.03(15) 2_656 . ?
C006 N001 C003 117.98(7) . 2_656 ?
C006 N001 C003 117.98(7) . . ?
N001 C003 C004 121.56(11) . . ?
C005 C003 N001 118.37(12) . . ?
C005 C003 C004 120.03(12) . . ?
C008 C004 C003 124.62(11) . . ?
C008 C004 C009 117.78(13) . . ?
C009 C004 C003 117.53(12) . . ?
C003 C005 C00A 120.77(12) . . ?
C003 C005 C00C 119.81(14) . . ?
C00C C005 C00A 119.15(13) . . ?
N001 C006 C007 119.96(10) . 2_656 ?
N001 C006 C007 119.96(10) . . ?
C007 C006 C007 120.1(2) 2_656 . ?
C006 C007 C00A 119.62(15) . . ?
C00F C007 C006 118.87(16) . . ?
C00F C007 C00A 121.48(15) . . ?
C004 C008 H008 119.5 . . ?
C00B C008 C004 121.08(13) . . ?
C00B C008 H008 119.5 . . ?
C00D C009 C004 119.06(14) . . ?
C00D C009 C00E 120.72(14) . . ?
C00E C009 C004 120.17(15) . . ?
O002 C00A C005 122.77(16) . . ?
O002 C00A C007 122.42(16) . . ?
C007 C00A C005 114.67(12) . . ?
C008 C00B H00B 119.8 . . ?
C008 C00B C00G 120.44(15) . . ?
C00G C00B H00B 119.8 . . ?
C005 C00C H00C 119.4 . . ?
C00E C00C C005 121.23(14) . . ?
C00E C00C H00C 119.4 . . ?
C009 C00D H00D 119.3 . . ?
C00G C00D C009 121.39(14) . . ?
C00G C00D H00D 119.3 . . ?
C009 C00E H00E 119.7 . . ?
C00C C00E C009 120.50(13) . . ?
C00C C00E H00E 119.7 . . ?
C007 C00F H00F 119.4 . . ?
C00H C00F C007 121.25(18) . . ?
C00H C00F H00F 119.4 . . ?
C00B C00G H00G 120.0 . . ?
C00D C00G C00B 119.99(15) . . ?
C00D C00G H00G 120.0 . . ?
C00F C00H C00F 119.7(2) 2_656 . ?
C00F C00H H00H 120.2 . . ?
C00F C00H H00H 120.2 2_656 . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-04-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.969
_oxdiff_exptl_absorpt_empirical_full_min 0.646
####################################################################### 
# 
# 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_mo_wym_5563_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2249621'
loop_
_audit_author_name
_audit_author_address
'Yimin Wu'
;Sichuan University
China
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2023-03-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H23 N O4'
_chemical_formula_sum            'C30 H23 N O4'
_chemical_formula_weight         461.49
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.7721(8)
_cell_length_b                   14.0494(8)
_cell_length_c                   12.9393(7)
_cell_angle_alpha                90
_cell_angle_beta                 120.406(3)
_cell_angle_gamma                90
_cell_volume                     2316.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6657
_cell_measurement_temperature    197(2)
_cell_measurement_theta_max      27.178
_cell_measurement_theta_min      2.244
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1080 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.8993.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27302
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      197.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2015
_reflns_number_total             2655
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.048
_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)+(0.0469P)²+0.9397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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 0.36808(7) 0.59986(7) 0.84391(8) 0.0341(2) Uani 1 1 d . . . . .
O2 O 0.40696(8) 0.75004(7) 0.82230(9) 0.0439(3) Uani 1 1 d . . . . .
N1 N 0.5000 0.50908(10) 0.7500 0.0240(3) Uani 1 2 d S T P . .
C1 C 0.90008(11) 0.49188(11) 1.03631(14) 0.0428(4) Uani 1 1 d . . . . .
H1 H 0.9725 0.4757 1.0785 0.051 Uiso 1 1 calc R U . . .
C2 C 0.86365(11) 0.56073(11) 1.07936(12) 0.0395(3) Uani 1 1 d . . . . .
H2 H 0.9113 0.5933 1.1509 0.047 Uiso 1 1 calc R U . . .
C3 C 0.75549(10) 0.58493(9) 1.01928(11) 0.0307(3) Uani 1 1 d . . . . .
C4 C 0.68394(9) 0.53502(8) 0.91290(10) 0.0261(3) Uani 1 1 d . . . . .
C5 C 0.57429(9) 0.55959(8) 0.85435(10) 0.0235(3) Uani 1 1 d . . . . .
C6 C 0.26192(11) 0.63035(12) 0.80650(14) 0.0471(4) Uani 1 1 d . . . . .
H6A H 0.2272 0.6519 0.7231 0.071 Uiso 1 1 calc R U . . .
H6B H 0.2643 0.6827 0.8578 0.071 Uiso 1 1 calc R U . . .
H6C H 0.2226 0.5769 0.8134 0.071 Uiso 1 1 calc R U . . .
C7 C 0.43254(10) 0.66800(9) 0.84765(10) 0.0278(3) Uani 1 1 d . . . . .
C8 C 0.54311(9) 0.63427(8) 0.89841(10) 0.0255(3) Uani 1 1 d . . . . .
C9 C 0.61709(10) 0.68634(9) 0.99999(11) 0.0320(3) Uani 1 1 d . . . . .
H9 H 0.5947 0.7401 1.0257 0.038 Uiso 1 1 calc R U . . .
C10 C 0.71947(10) 0.66028(10) 1.06092(11) 0.0353(3) Uani 1 1 d . . . . .
H10 H 0.7673 0.6931 1.1322 0.042 Uiso 1 1 calc R U . . .
C11 C 0.72583(10) 0.46533(9) 0.86904(12) 0.0331(3) Uani 1 1 d . . . . .
H11 H 0.6802 0.4327 0.7967 0.040 Uiso 1 1 calc R U . . .
C12 C 0.83061(11) 0.44441(10) 0.92904(13) 0.0402(3) Uani 1 1 d . . . . .
H12 H 0.8568 0.3974 0.8981 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5000 0.40806(12) 0.7500 0.0255(4) Uani 1 2 d S T P . .
C14 C 0.53194(10) 0.35792(9) 0.85565(11) 0.0310(3) Uani 1 1 d . . . . .
H14 H 0.5527 0.3914 0.9281 0.037 Uiso 1 1 calc R U . . .
C15 C 0.53355(12) 0.25941(9) 0.85552(12) 0.0373(3) Uani 1 1 d . . . . .
H15 H 0.5579 0.2257 0.9285 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5000 0.20970(14) 0.7500 0.0392(5) Uani 1 2 d S T P . .
H16 H 0.5000 0.1421 0.7500 0.047 Uiso 1 2 calc R U P . .


_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 C6 1.4522(16) . ?
O1 C7 1.3338(16) . ?
O2 C7 1.2056(15) . ?
N1 C5 1.4252(13) 2_656 ?
N1 C5 1.4252(13) . ?
N1 C13 1.419(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.356(2) . ?
C1 C12 1.408(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.4196(18) . ?
C3 C4 1.4251(17) . ?
C3 C10 1.4085(19) . ?
C4 C5 1.4404(16) . ?
C4 C11 1.4209(18) . ?
C5 C8 1.3797(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.4959(17) . ?
C8 C9 1.4153(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3550(19) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.3669(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3910(15) . ?
C13 C14 1.3910(15) 2_656 ?
C14 H14 0.9500 . ?
C14 C15 1.3842(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3830(17) . ?
C16 C15 1.3830(17) 2_656 ?
C16 H16 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
C7 O1 C6 115.53(11) . . ?
C5 N1 C5 120.27(13) 2_656 . ?
C13 N1 C5 119.86(7) . . ?
C13 N1 C5 119.86(7) . 2_656 ?
C2 C1 H1 120.0 . . ?
C2 C1 C12 120.00(13) . . ?
C12 C1 H1 120.0 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.10(13) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 119.34(12) . . ?
C10 C3 C2 120.59(12) . . ?
C10 C3 C4 120.01(12) . . ?
C3 C4 C5 118.49(11) . . ?
C11 C4 C3 117.70(12) . . ?
C11 C4 C5 123.79(11) . . ?
N1 C5 C4 120.05(10) . . ?
C8 C5 N1 120.80(10) . . ?
C8 C5 C4 119.12(10) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 112.91(10) . . ?
O2 C7 O1 123.82(12) . . ?
O2 C7 C8 122.99(12) . . ?
C5 C8 C7 125.32(10) . . ?
C5 C8 C9 120.96(11) . . ?
C9 C8 C7 113.72(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.70(12) . . ?
C10 C9 H9 119.6 . . ?
C3 C10 H10 119.8 . . ?
C9 C10 C3 120.46(12) . . ?
C9 C10 H10 119.8 . . ?
C4 C11 H11 119.4 . . ?
C12 C11 C4 121.21(13) . . ?
C12 C11 H11 119.4 . . ?
C1 C12 H12 119.7 . . ?
C11 C12 C1 120.59(14) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 N1 120.43(8) 2_656 . ?
C14 C13 N1 120.43(8) . . ?
C14 C13 C14 119.15(16) . 2_656 ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.17(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.55(13) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C15 119.34(17) 2_656 . ?
C15 C16 H16 120.3 2_656 . ?
C15 C16 H16 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C5 57.44(15) . . . . ?
O1 C7 C8 C9 -122.22(12) . . . . ?
O2 C7 C8 C5 -128.29(14) . . . . ?
O2 C7 C8 C9 52.05(16) . . . . ?
N1 C5 C8 C7 2.19(18) . . . . ?
N1 C5 C8 C9 -178.17(11) . . . . ?
N1 C13 C14 C15 -178.85(10) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C1 C2 C3 C10 -176.29(13) . . . . ?
C2 C1 C12 C11 -1.7(2) . . . . ?
C2 C3 C4 C5 179.02(12) . . . . ?
C2 C3 C4 C11 -2.63(18) . . . . ?
C2 C3 C10 C9 176.66(13) . . . . ?
C3 C4 C5 N1 -177.96(10) . . . . ?
C3 C4 C5 C8 4.09(17) . . . . ?
C3 C4 C11 C12 2.30(19) . . . . ?
C4 C3 C10 C9 -0.5(2) . . . . ?
C4 C5 C8 C7 -179.88(11) . . . . ?
C4 C5 C8 C9 -0.24(18) . . . . ?
C4 C11 C12 C1 -0.2(2) . . . . ?
C5 N1 C5 C4 -130.64(12) 2_656 . . . ?
C5 N1 C5 C8 47.27(9) 2_656 . . . ?
C5 N1 C13 C14 -149.85(9) 2_656 . . . ?
C5 N1 C13 C14 30.15(9) . . . . ?
C5 N1 C13 C14 30.15(9) 2_656 . . 2_656 ?
C5 N1 C13 C14 -149.85(9) . . . 2_656 ?
C5 C4 C11 C12 -179.45(12) . . . . ?
C5 C8 C9 C10 -4.17(19) . . . . ?
C6 O1 C7 O2 0.01(17) . . . . ?
C6 O1 C7 C8 174.23(10) . . . . ?
C7 C8 C9 C10 175.51(12) . . . . ?
C8 C9 C10 C3 4.5(2) . . . . ?
C10 C3 C4 C5 -3.78(18) . . . . ?
C10 C3 C4 C11 174.57(12) . . . . ?
C11 C4 C5 N1 3.80(18) . . . . ?
C11 C4 C5 C8 -174.15(12) . . . . ?
C12 C1 C2 C3 1.3(2) . . . . ?
C13 N1 C5 C4 49.35(12) . . . . ?
C13 N1 C5 C8 -132.73(9) . . . . ?
C13 C14 C15 C16 -2.32(19) . . . . ?
C14 C13 C14 C15 1.15(10) 2_656 . . . ?
C14 C15 C16 C15 1.16(10) . . . 2_656 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_wym_ch4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2249111'
loop_
_audit_author_name
_audit_author_address
'Yimin Wu'
;Sichuan University
China
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H9 N O2'
_chemical_formula_sum            'C20 H9 N O2'
_chemical_formula_weight         295.28
_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 0.0033 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           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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   3.7973(3)
_cell_length_b                   17.7163(14)
_cell_length_c                   19.1364(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1287.38(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1158
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.730
_cell_measurement_theta_min      2.419
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1007 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.8828.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7439
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                1596
_reflns_number_total             2840
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 398 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.019
_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)+(0.0412P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1322
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16),
 C19(H19)
;
_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 0.8656(10) 0.61954(17) 0.54217(15) 0.0598(10) Uani 1 1 d . . . . .
O2 O 0.4646(10) 0.27700(18) 0.35420(18) 0.0732(12) Uani 1 1 d . . . . .
N1 N 0.4932(9) 0.50269(18) 0.37748(15) 0.0378(9) Uani 1 1 d . . . . .
C1 C 0.8790(14) 0.3795(3) 0.5390(2) 0.0532(13) Uani 1 1 d . . . . .
H1 H 0.9634 0.3511 0.5763 0.064 Uiso 1 1 calc R U . . .
C2 C 0.7531(13) 0.3423(3) 0.4803(2) 0.0527(13) Uani 1 1 d . . . . .
H2 H 0.7594 0.2899 0.4786 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6179(12) 0.3825(2) 0.4244(2) 0.0420(11) Uani 1 1 d . . . . .
C4 C 0.4703(13) 0.3463(3) 0.3598(2) 0.0497(13) Uani 1 1 d . . . . .
C5 C 0.3351(12) 0.3972(2) 0.3055(2) 0.0431(11) Uani 1 1 d . . . . .
C6 C 0.3525(11) 0.4739(2) 0.31770(19) 0.0368(10) Uani 1 1 d . . . . .
C7 C 0.2443(10) 0.5332(3) 0.27378(19) 0.0389(10) Uani 1 1 d . . . . .
C8 C 0.0983(12) 0.5112(3) 0.2108(2) 0.0489(12) Uani 1 1 d . . . . .
H8 H 0.0181 0.5470 0.1790 0.059 Uiso 1 1 calc R U . . .
C9 C 0.3985(14) 0.7278(3) 0.3581(2) 0.0520(13) Uani 1 1 d . . . . .
H9 H 0.3699 0.7796 0.3526 0.062 Uiso 1 1 calc R U . . .
C10 C 0.2888(12) 0.6799(2) 0.3038(2) 0.0479(12) Uani 1 1 d . . . . .
H10 H 0.1935 0.6996 0.2629 0.057 Uiso 1 1 calc R U . . .
C11 C 0.3255(11) 0.6032(2) 0.3125(2) 0.0390(11) Uani 1 1 d . . . . .
C12 C 0.0736(13) 0.4342(3) 0.1957(2) 0.0560(14) Uani 1 1 d . . . . .
H12 H -0.0224 0.4199 0.1530 0.067 Uiso 1 1 calc R U . . .
C13 C 0.1846(13) 0.3780(3) 0.2411(2) 0.0534(13) Uani 1 1 d . . . . .
H13 H 0.1592 0.3275 0.2287 0.064 Uiso 1 1 calc R U . . .
C14 C 0.6222(11) 0.4615(2) 0.43108(19) 0.0366(10) Uani 1 1 d . . . . .
C15 C 0.7529(12) 0.5006(3) 0.48937(19) 0.0375(10) Uani 1 1 d . . . . .
C16 C 0.8831(12) 0.4577(3) 0.5437(2) 0.0479(12) Uani 1 1 d . . . . .
H16 H 0.9732 0.4810 0.5834 0.057 Uiso 1 1 calc R U . . .
C17 C 0.7454(12) 0.5856(3) 0.4917(2) 0.0426(12) Uani 1 1 d . . . . .
C18 C 0.5933(12) 0.6238(2) 0.43015(19) 0.0379(11) Uani 1 1 d . . . . .
C19 C 0.5476(12) 0.7012(2) 0.4196(2) 0.0462(12) Uani 1 1 d . . . . .
H19 H 0.6175 0.7352 0.4540 0.055 Uiso 1 1 calc R U . . .
C20 C 0.4752(12) 0.5797(2) 0.3756(2) 0.0359(10) 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
O1 C17 1.227(5) . ?
O2 C4 1.232(5) . ?
N1 C6 1.362(5) . ?
N1 C14 1.350(5) . ?
N1 C20 1.367(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(6) . ?
C1 C16 1.388(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(6) . ?
C3 C4 1.501(6) . ?
C3 C14 1.406(5) . ?
C4 C5 1.470(6) . ?
C5 C6 1.379(5) . ?
C5 C13 1.400(6) . ?
C6 C7 1.408(5) . ?
C7 C8 1.384(5) . ?
C7 C11 1.476(5) . ?
C8 H8 0.9300 . ?
C8 C12 1.397(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.405(6) . ?
C9 C19 1.389(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(6) . ?
C11 C20 1.398(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.403(5) . ?
C15 C16 1.380(5) . ?
C15 C17 1.507(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.475(6) . ?
C18 C19 1.397(5) . ?
C18 C20 1.379(5) . ?
C19 H19 0.9300 . ?

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
C6 N1 C20 109.4(3) . . ?
C14 N1 C6 125.3(3) . . ?
C14 N1 C20 125.3(4) . . ?
C2 C1 H1 119.0 . . ?
C2 C1 C16 122.0(4) . . ?
C16 C1 H1 119.0 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 123.7(4) . . ?
C2 C3 C14 116.0(4) . . ?
C14 C3 C4 120.4(4) . . ?
O2 C4 C3 120.3(4) . . ?
O2 C4 C5 122.9(5) . . ?
C5 C4 C3 116.7(4) . . ?
C6 C5 C4 117.9(4) . . ?
C6 C5 C13 114.1(4) . . ?
C13 C5 C4 128.0(4) . . ?
N1 C6 C5 122.0(4) . . ?
N1 C6 C7 109.6(3) . . ?
C5 C6 C7 128.3(4) . . ?
C6 C7 C11 105.5(3) . . ?
C8 C7 C6 115.2(4) . . ?
C8 C7 C11 139.3(4) . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C12 118.8(4) . . ?
C12 C8 H8 120.6 . . ?
C10 C9 H9 118.5 . . ?
C19 C9 H9 118.5 . . ?
C19 C9 C10 122.9(4) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.5(4) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 C7 138.3(4) . . ?
C10 C11 C20 116.0(4) . . ?
C20 C11 C7 105.6(4) . . ?
C8 C12 H12 118.3 . . ?
C13 C12 C8 123.5(4) . . ?
C13 C12 H12 118.3 . . ?
C5 C13 H13 120.0 . . ?
C12 C13 C5 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
N1 C14 C3 117.7(4) . . ?
N1 C14 C15 117.8(4) . . ?
C15 C14 C3 124.6(4) . . ?
C14 C15 C17 120.6(4) . . ?
C16 C15 C14 117.0(4) . . ?
C16 C15 C17 122.4(4) . . ?
C1 C16 H16 120.1 . . ?
C15 C16 C1 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
O1 C17 C15 120.4(4) . . ?
O1 C17 C18 123.3(4) . . ?
C18 C17 C15 116.3(4) . . ?
C19 C18 C17 127.9(4) . . ?
C20 C18 C17 118.1(4) . . ?
C20 C18 C19 114.0(4) . . ?
C9 C19 C18 120.3(4) . . ?
C9 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N1 C20 C11 109.9(4) . . ?
N1 C20 C18 122.0(4) . . ?
C18 C20 C11 128.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C18 C19 -2.6(7) . . . . ?
O1 C17 C18 C20 178.2(4) . . . . ?
O2 C4 C5 C6 179.5(5) . . . . ?
O2 C4 C5 C13 -0.2(8) . . . . ?
N1 C6 C7 C8 179.5(4) . . . . ?
N1 C6 C7 C11 -1.0(4) . . . . ?
N1 C14 C15 C16 179.9(4) . . . . ?
N1 C14 C15 C17 0.5(6) . . . . ?
C1 C2 C3 C4 -178.7(5) . . . . ?
C1 C2 C3 C14 0.7(7) . . . . ?
C2 C1 C16 C15 1.2(7) . . . . ?
C2 C3 C4 O2 -0.1(7) . . . . ?
C2 C3 C4 C5 179.6(4) . . . . ?
C2 C3 C14 N1 179.8(4) . . . . ?
C2 C3 C14 C15 0.3(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C3 C4 C5 C13 -179.8(4) . . . . ?
C3 C14 C15 C16 -0.5(6) . . . . ?
C3 C14 C15 C17 -179.9(4) . . . . ?
C4 C3 C14 N1 -0.7(6) . . . . ?
C4 C3 C14 C15 179.7(4) . . . . ?
C4 C5 C6 N1 0.8(6) . . . . ?
C4 C5 C6 C7 179.3(4) . . . . ?
C4 C5 C13 C12 -179.4(4) . . . . ?
C5 C6 C7 C8 0.8(6) . . . . ?
C5 C6 C7 C11 -179.6(4) . . . . ?
C6 N1 C14 C3 1.3(6) . . . . ?
C6 N1 C14 C15 -179.0(4) . . . . ?
C6 N1 C20 C11 -1.2(5) . . . . ?
C6 N1 C20 C18 178.8(4) . . . . ?
C6 C5 C13 C12 0.9(6) . . . . ?
C6 C7 C8 C12 -0.6(6) . . . . ?
C6 C7 C11 C10 -178.3(5) . . . . ?
C6 C7 C11 C20 0.2(4) . . . . ?
C7 C8 C12 C13 0.7(7) . . . . ?
C7 C11 C20 N1 0.6(5) . . . . ?
C7 C11 C20 C18 -179.4(4) . . . . ?
C8 C7 C11 C10 1.0(9) . . . . ?
C8 C7 C11 C20 179.5(5) . . . . ?
C8 C12 C13 C5 -0.9(8) . . . . ?
C9 C10 C11 C7 177.7(5) . . . . ?
C9 C10 C11 C20 -0.7(6) . . . . ?
C10 C9 C19 C18 -0.4(8) . . . . ?
C10 C11 C20 N1 179.5(4) . . . . ?
C10 C11 C20 C18 -0.5(7) . . . . ?
C11 C7 C8 C12 -179.9(5) . . . . ?
C13 C5 C6 N1 -179.5(4) . . . . ?
C13 C5 C6 C7 -1.0(6) . . . . ?
C14 N1 C6 C5 -1.4(7) . . . . ?
C14 N1 C6 C7 179.8(4) . . . . ?
C14 N1 C20 C11 -179.6(4) . . . . ?
C14 N1 C20 C18 0.4(7) . . . . ?
C14 C3 C4 O2 -179.5(4) . . . . ?
C14 C3 C4 C5 0.1(6) . . . . ?
C14 C15 C16 C1 -0.2(6) . . . . ?
C14 C15 C17 O1 -178.7(4) . . . . ?
C14 C15 C17 C18 0.3(6) . . . . ?
C15 C17 C18 C19 178.4(4) . . . . ?
C15 C17 C18 C20 -0.8(6) . . . . ?
C16 C1 C2 C3 -1.5(7) . . . . ?
C16 C15 C17 O1 1.9(7) . . . . ?
C16 C15 C17 C18 -179.1(4) . . . . ?
C17 C15 C16 C1 179.2(4) . . . . ?
C17 C18 C19 C9 -180.0(5) . . . . ?
C17 C18 C20 N1 0.5(7) . . . . ?
C17 C18 C20 C11 -179.5(4) . . . . ?
C19 C9 C10 C11 1.1(8) . . . . ?
C19 C18 C20 N1 -178.8(4) . . . . ?
C19 C18 C20 C11 1.2(7) . . . . ?
C20 N1 C6 C5 -179.8(4) . . . . ?
C20 N1 C6 C7 1.4(5) . . . . ?
C20 N1 C14 C3 179.5(4) . . . . ?
C20 N1 C14 C15 -0.9(6) . . . . ?
C20 C18 C19 C9 -0.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_wym_hph4_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2249112'
loop_
_audit_author_name
_audit_author_address
'Yimin Wu'
;Sichuan University
China
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2023-01-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H13 N O2'
_chemical_formula_sum            'C26 H13 N O2'
_chemical_formula_weight         371.37
_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 0.0033 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           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   16.208(4)
_cell_length_b                   4.0870(10)
_cell_length_c                   12.278(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     813.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.272
_cell_measurement_theta_min      2.513
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8832.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4870
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         2.081
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                1479
_reflns_number_total             1841
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 519 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.058
_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)+(0.0395P)²+0.0918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14)
;
_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 0.28577(15) 0.4606(7) 0.74696(19) 0.0391(7) Uani 1 1 d . . . . .
N1 N 0.5000 0.3644(9) 0.5652(3) 0.0214(8) Uani 1 2 d S T P . .
C1 C 0.5000 0.8724(12) 0.8672(4) 0.0336(12) Uani 1 2 d S T P . .
H1 H 0.5000 1.0119 0.9291 0.040 Uiso 1 2 calc R U P . .
C2 C 0.4271(2) 0.7680(9) 0.8209(3) 0.0315(8) Uani 1 1 d . . . . .
H2 H 0.3763 0.8214 0.8552 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4262(2) 0.5861(8) 0.7249(2) 0.0249(7) Uani 1 1 d . . . . .
C4 C 0.5000 0.5120(10) 0.6689(3) 0.0229(10) Uani 1 2 d S T P . .
C5 C 0.42189(19) 0.2482(8) 0.5235(2) 0.0216(6) Uani 1 1 d . . . . .
C6 C 0.4084(2) 0.1452(8) 0.4142(3) 0.0245(7) Uani 1 1 d . . . . .
C7 C 0.4573(2) 0.2519(9) 0.3185(3) 0.0249(7) Uani 1 1 d . . . . .
C8 C 0.4148(2) 0.3545(9) 0.2252(3) 0.0310(8) Uani 1 1 d . . . . .
H8 H 0.3562 0.3570 0.2252 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4576(2) 0.4529(9) 0.1326(3) 0.0360(9) Uani 1 1 d . . . . .
H9 H 0.4282 0.5200 0.0694 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3491(2) 0.4316(8) 0.6926(2) 0.0276(8) Uani 1 1 d . . . . .
C11 C 0.3522(2) 0.2414(8) 0.5925(2) 0.0252(7) Uani 1 1 d . . . . .
C12 C 0.2803(2) 0.0749(8) 0.5633(3) 0.0297(8) Uani 1 1 d . . . . .
H12 H 0.2350 0.0697 0.6123 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2741(2) -0.0803(9) 0.4652(3) 0.0315(8) Uani 1 1 d . . . . .
H13 H 0.2287 -0.2184 0.4488 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3369(2) -0.0284(9) 0.3907(3) 0.0292(7) Uani 1 1 d . . . . .
H14 H 0.3307 -0.1163 0.3196 0.035 Uiso 1 1 calc R U . . .


_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 C10 1.230(4) . ?
N1 C4 1.409(6) . ?
N1 C5 1.446(3) . ?
N1 C5 1.446(3) 3_655 ?
C1 H1 0.9500 . ?
C1 C2 1.379(4) 3_655 ?
C1 C2 1.379(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(4) . ?
C3 C4 1.413(4) . ?
C3 C10 1.455(5) . ?
C4 C3 1.413(4) 3_655 ?
C5 C6 1.423(4) . ?
C5 C11 1.412(4) . ?
C6 C7 1.483(4) . ?
C6 C14 1.389(5) . ?
C7 C7 1.386(6) 3_655 ?
C7 C8 1.400(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(5) . ?
C9 C9 1.375(8) 3_655 ?
C9 H9 0.9500 . ?
C10 C11 1.456(4) . ?
C11 C12 1.397(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.364(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(5) . ?
C14 H14 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
C4 N1 C5 117.43(18) . 3_655 ?
C4 N1 C5 117.43(18) . . ?
C5 N1 C5 122.2(4) 3_655 . ?
C2 C1 H1 121.0 . . ?
C2 C1 H1 121.0 3_655 . ?
C2 C1 C2 117.9(5) 3_655 . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 C10 118.1(3) . . ?
C4 C3 C10 120.1(3) . . ?
N1 C4 C3 122.1(2) . 3_655 ?
N1 C4 C3 122.1(2) . . ?
C3 C4 C3 115.7(4) 3_655 . ?
C6 C5 N1 124.4(3) . . ?
C11 C5 N1 119.6(3) . . ?
C11 C5 C6 115.9(3) . . ?
C5 C6 C7 125.3(3) . . ?
C14 C6 C5 118.4(3) . . ?
C14 C6 C7 115.6(3) . . ?
C7 C7 C6 122.29(18) 3_655 . ?
C7 C7 C8 119.4(2) 3_655 . ?
C8 C7 C6 118.3(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.1 . . ?
C9 C9 C8 119.9(2) 3_655 . ?
C9 C9 H9 120.1 3_655 . ?
O1 C10 C3 121.8(3) . . ?
O1 C10 C11 122.6(3) . . ?
C3 C10 C11 115.6(3) . . ?
C5 C11 C10 121.6(3) . . ?
C12 C11 C5 121.5(3) . . ?
C12 C11 C10 116.6(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 121.4 . . ?
C12 C13 C14 117.3(3) . . ?
C14 C13 H13 121.4 . . ?
C6 C14 H14 118.2 . . ?
C13 C14 C6 123.7(3) . . ?
C13 C14 H14 118.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 C5 171.0(3) . . . . ?
O1 C10 C11 C12 -3.5(5) . . . . ?
N1 C5 C6 C7 -24.8(5) . . . . ?
N1 C5 C6 C14 165.7(3) . . . . ?
N1 C5 C11 C10 18.2(5) . . . . ?
N1 C5 C11 C12 -167.5(3) . . . . ?
C1 C2 C3 C4 -2.5(5) . . . . ?
C1 C2 C3 C10 168.3(4) . . . . ?
C2 C1 C2 C3 -5.4(7) 3_655 . . . ?
C2 C3 C4 N1 -171.9(3) . . . . ?
C2 C3 C4 C3 9.9(6) . . . 3_655 ?
C2 C3 C10 O1 0.6(5) . . . . ?
C2 C3 C10 C11 -179.2(3) . . . . ?
C3 C10 C11 C5 -9.1(4) . . . . ?
C3 C10 C11 C12 176.3(3) . . . . ?
C4 N1 C5 C6 168.9(3) . . . . ?
C4 N1 C5 C11 -9.3(5) . . . . ?
C4 C3 C10 O1 171.4(3) . . . . ?
C4 C3 C10 C11 -8.4(4) . . . . ?
C5 N1 C4 C3 8.5(5) 3_655 . . 3_655 ?
C5 N1 C4 C3 169.6(3) . . . 3_655 ?
C5 N1 C4 C3 -8.5(5) . . . . ?
C5 N1 C4 C3 -169.6(3) 3_655 . . . ?
C5 N1 C5 C6 -31.0(6) 3_655 . . . ?
C5 N1 C5 C11 150.9(3) 3_655 . . . ?
C5 C6 C7 C7 47.9(4) . . . 3_655 ?
C5 C6 C7 C8 -132.4(3) . . . . ?
C5 C6 C14 C13 6.4(5) . . . . ?
C5 C11 C12 C13 -1.8(5) . . . . ?
C6 C5 C11 C10 -160.0(3) . . . . ?
C6 C5 C11 C12 14.2(4) . . . . ?
C6 C7 C8 C9 -179.1(3) . . . . ?
C7 C6 C14 C13 -164.1(3) . . . . ?
C7 C7 C8 C9 0.6(4) 3_655 . . . ?
C7 C8 C9 C9 -0.6(4) . . . 3_655 ?
C10 C3 C4 N1 17.5(5) . . . . ?
C10 C3 C4 C3 -160.6(2) . . . 3_655 ?
C10 C11 C12 C13 172.8(3) . . . . ?
C11 C5 C6 C7 153.3(3) . . . . ?
C11 C5 C6 C14 -16.2(4) . . . . ?
C11 C12 C13 C14 -8.7(5) . . . . ?
C12 C13 C14 C6 6.4(5) . . . . ?
C14 C6 C7 C7 -142.4(2) . . . 3_655 ?
C14 C6 C7 C8 37.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
