# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_fww-100k
_database_code_depnum_ccdc_archive 'CCDC 2111659'
loop_
_audit_author_name
_audit_author_address
'Long-jie Wang'
;Yunnan university
China
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_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      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                   3.80620(10)
_cell_length_b                   12.7167(3)
_cell_length_c                   13.5789(2)
_cell_angle_alpha                67.404(2)
_cell_angle_beta                 87.172(2)
_cell_angle_gamma                89.413(2)
_cell_volume                     606.03(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6839
_cell_measurement_temperature    101(3)
_cell_measurement_theta_max      75.6240
_cell_measurement_theta_min      3.7440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7822
_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         75.818
_diffrn_reflns_theta_min         3.530
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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     84.00 175.00   0.50    0.40    --  111.82  45.00   0.00  182
  2  ω     90.00 175.00   0.50    0.40    --  111.82  45.00  60.00  170
  3  ω     83.00 175.00   0.50    0.40    --  111.82  45.00 120.00  184
  4  ω     95.00 175.00   0.50    0.40    --  111.82  30.00 150.00  160
  5  ω     36.00  71.00   0.50    0.40    --  111.82  15.00 -90.00   70
  6  ω     79.00 137.00   0.50    0.40    --  111.82  15.00 -90.00  116
  7  ω     91.00 147.00   0.50    0.40    --  111.82  45.00 -60.00  112
  8  ω     85.00 155.00   0.50    0.40    --  111.82  77.00-120.00  140
  9  ω    -66.00  33.00   0.50    0.15    --  -39.20  57.00 150.00  198
 10  ω    -29.00  42.00   0.50    0.15    --  -39.20  19.00 -90.00  142
 11  ω     -9.00  21.00   0.50    0.40    --  -62.00  15.00-150.00   60
 12  ω    -25.00   2.00   0.50    0.40    --  -62.00  15.00   0.00   54
 13  ω    -27.00  16.00   0.50    0.40    --  -62.00  15.00  90.00   86
 14  ω    -38.00  17.00   0.50    0.40    --  -62.00  30.00 120.00  110
 15  ω     88.00 114.00   0.50    0.40    --  111.82 179.00  90.00   52
 16  ω     85.00 110.00   0.50    0.40    --  111.82 155.00 154.00   50
 17  ω     65.00  91.00   0.50    0.15    --   39.20 155.00 154.00   52
 18  ω     85.00 111.00   0.50    0.40    --  111.82 120.00  -2.00   52
 19  ω    113.00 175.00   0.50    0.40    --  111.82 111.00 -30.00  124
 20  ω     98.00 146.00   0.50    0.40    --  111.82 179.00-150.00   96
 21  ω     42.00  79.00   0.50    0.40    --  111.82 179.00-150.00   74
 22  ω    -44.00  23.00   0.50    0.15    --   39.20 -19.00 -30.00  134
 23  ω     38.00  67.00   0.50    0.40    --  111.82 -61.00-180.00   58
 24  ω     44.00  70.00   0.50    0.40    --  111.82 -77.00 -90.00   52
 25  ω     38.00  68.00   0.50    0.40    --  111.82 -61.00 -90.00   60
 26  ω     41.00  68.00   0.50    0.40    --  111.82 -61.00 -30.00   54
 27  ω     38.00  67.00   0.50    0.40    --  111.82 -61.00   0.00   58
 28  ω     38.00  98.00   0.50    0.40    --  111.82 -77.00  90.00  120
 29  ω     38.00  63.00   0.50    0.40    --  111.82 -61.00 120.00   50
 30  ω     38.00  68.00   0.50    0.40    --  111.82 -61.00 150.00   60
 31  ω    -43.00  23.00   0.50    0.15    --   39.20 -19.00  90.00  132
 32  ω     68.00 102.00   0.50    0.40    --  111.82 -94.00 -30.00   68
 33  ω     33.00 106.00   0.50    0.40    --  111.82-120.00 -87.00  146
 34  ω     37.00  67.00   0.50    0.40    --  111.82-111.00-180.00   60
 35  ω     71.00 108.00   0.50    0.40    --  111.82-111.00-180.00   74
 36  ω     20.00  96.00   0.50    0.15    --   39.20-120.00 -87.00  152
 37  ω     32.00  97.00   0.50    0.40    --  111.82-111.00 -60.00  130
 38  ω     69.00 108.00   0.50    0.40    --  111.82-111.00 -30.00   78
 39  ω     82.00 108.00   0.50    0.40    --  111.82-111.00   0.00   52
 40  ω     81.00 114.00   0.50    0.40    --  111.82-155.00 115.00   66
 41  ω     33.00 108.00   0.50    0.40    --  111.82-111.00  90.00  150
 42  ω     34.00  59.00   0.50    0.40    --  111.82-111.00  60.00   50
 43  ω     67.00 108.00   0.50    0.40    --  111.82-111.00  60.00   82
 44  ω     34.00 104.00   0.50    0.40    --  111.82 -94.00  90.00  140
 45  ω     63.00  91.00   0.50    0.15    --   39.20-155.00 115.00   56
 46  ω     32.00  58.00   0.50    0.40    --  111.82-111.00   0.00   52
 47  ω     33.00  58.00   0.50    0.40    --  111.82 -94.00 -30.00   50
 48  ω     50.00 102.00   0.50    0.40    --  111.82-111.00 -90.00  104
 49  ω     48.00  86.00   0.50    0.40    --  111.82 -94.00-180.00   76
 50  ω    -79.00 -42.00   0.50    0.15    --  -39.20 120.00  -2.00   74
 51  ω    -89.00 -64.00   0.50    0.40    --  -62.00 120.00  -2.00   50
 52  ω   -112.00 -71.00   0.50    0.15    --  -39.20 155.00 154.00   82
 53  ω   -109.00 -84.00   0.50    0.40    --  -62.00 155.00 154.00   50
 54  ω   -113.00 -88.00   0.50    0.15    --  -39.20-155.00 115.00   50
 55  ω   -124.00 -99.00   0.50    0.40    --  -62.00-155.00 115.00   50
 56  ω   -142.00-109.00   0.50    0.40    --  -62.00-111.00  30.00   66
 57  ω   -136.00-111.00   0.50    0.40    --  -62.00-120.00 -87.00   50
 58  ω   -142.00 -90.00   0.50    0.40    --  -62.00-111.00-180.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2277012000
_diffrn_orient_matrix_UB_12      -0.0931577000
_diffrn_orient_matrix_UB_13      -0.0124940000
_diffrn_orient_matrix_UB_21      -0.2622417000
_diffrn_orient_matrix_UB_22      0.0911462000
_diffrn_orient_matrix_UB_23      -0.0632534000
_diffrn_orient_matrix_UB_31      0.2088466000
_diffrn_orient_matrix_UB_32      0.0152853000
_diffrn_orient_matrix_UB_33      -0.1047874000
_diffrn_oxdiff_digest_frames     
;
017bd92b2b3c0a75fc4b947e8486df793105224c127
;
_diffrn_oxdiff_digest_hkl        
;
0159642a3dc654eea8c2da385964178cc2ba12
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2375
_reflns_number_total             2462
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.095
_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)+(0.0734P)²+0.5107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1595
_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. Rigid bond restraints
 O004, C00F, C00J
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00h), C00H(H00i),
 C00I(H00j), C003(H003), C005(H005), C008(H008)
3.b Idealised Me refined as rotating group:
 C00F(H00a,H00f,H00g)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O004 O 0.6085(6) 0.12723(16) 0.69905(14) 0.0650(6) Uani 1 1 d . U . . .
N001 N 0.9193(4) 0.61386(12) 0.86272(11) 0.0222(3) Uani 1 1 d . . . . .
C00A C 0.5876(5) 0.28742(16) 0.75492(14) 0.0283(4) Uani 1 1 d . . . . .
C00B C 0.8055(5) 0.47419(17) 0.63996(14) 0.0288(4) Uani 1 1 d . . . . .
H00B H 0.922790 0.522263 0.575060 0.035 Uiso 1 1 calc R . . . .
C00C C 0.6567(5) 0.71997(17) 0.58543(14) 0.0321(4) Uani 1 1 d . . . . .
H00C H 0.579602 0.691309 0.534969 0.038 Uiso 1 1 calc R . . . .
C00D C 1.0831(5) 0.77369(15) 0.90503(15) 0.0305(4) Uani 1 1 d . . . . .
H00D H 1.165236 0.799863 0.956638 0.037 Uiso 1 1 calc R . . . .
C00E C 0.8099(5) 0.88173(17) 0.62483(17) 0.0381(5) Uani 1 1 d . . . . .
H00E H 0.837694 0.961733 0.603331 0.046 Uiso 1 1 calc R . . . .
C00F C 0.3921(7) 0.0934(2) 0.87458(18) 0.0468(5) Uani 1 1 d . U . . .
H00A H 0.383778 0.015136 0.877721 0.070 Uiso 1 1 calc GR . . . .
H00F H 0.153720 0.117687 0.886089 0.070 Uiso 1 1 calc GR . . . .
H00G H 0.541201 0.096589 0.930175 0.070 Uiso 1 1 calc GR . . . .
C00G C 0.7572(5) 0.35952(17) 0.65991(15) 0.0313(4) Uani 1 1 d . . . . .
H00H H 0.840319 0.330110 0.608552 0.038 Uiso 1 1 calc R . . . .
C00H C 1.0111(5) 0.84871(16) 0.80538(17) 0.0354(5) Uani 1 1 d . . . . .
H00I H 1.043966 0.928147 0.786591 0.042 Uiso 1 1 calc R . . . .
C00I C 0.6962(5) 0.83852(17) 0.55471(16) 0.0375(5) Uani 1 1 d . . . . .
H00J H 0.643019 0.888467 0.484591 0.045 Uiso 1 1 calc R . . . .
C00J C 0.5292(6) 0.16469(18) 0.77572(17) 0.0401(5) Uani 1 1 d . U . . .
C002 C 0.8436(4) 0.68821(14) 0.76225(13) 0.0233(4) Uani 1 1 d . . . . .
C003 C 0.5151(4) 0.44713(14) 0.80908(13) 0.0236(4) Uani 1 1 d . . . . .
H003 H 0.430955 0.476332 0.860490 0.028 Uiso 1 1 calc R . . . .
C005 C 0.4692(4) 0.33276(15) 0.82912(13) 0.0259(4) Uani 1 1 d . . . . .
H005 H 0.355244 0.284332 0.894480 0.031 Uiso 1 1 calc R . . . .
C006 C 0.7271(4) 0.64401(15) 0.68719(13) 0.0249(4) Uani 1 1 d . . . . .
C007 C 0.8876(4) 0.80796(15) 0.73015(15) 0.0294(4) Uani 1 1 d . . . . .
C008 C 1.0331(4) 0.65607(15) 0.93002(13) 0.0243(4) Uani 1 1 d . . . . .
H008 H 1.084734 0.604352 0.999626 0.029 Uiso 1 1 calc R . . . .
C009 C 0.6842(4) 0.52007(15) 0.71381(13) 0.0238(4) 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
O004 C00J 1.323(3) . ?
N001 C002 1.371(2) . ?
N001 C008 1.316(2) . ?
C00A C00G 1.394(3) . ?
C00A C00J 1.492(3) . ?
C00A C005 1.395(2) . ?
C00B H00B 0.9500 . ?
C00B C00G 1.389(3) . ?
C00B C009 1.399(2) . ?
C00C H00C 0.9500 . ?
C00C C00I 1.409(3) . ?
C00C C006 1.385(2) . ?
C00D H00D 0.9500 . ?
C00D C00H 1.362(3) . ?
C00D C008 1.414(2) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.358(3) . ?
C00E C007 1.420(3) . ?
C00F H00A 0.9800 . ?
C00F H00F 0.9800 . ?
C00F H00G 0.9800 . ?
C00F C00J 1.379(3) . ?
C00G H00H 0.9500 . ?
C00H H00I 0.9500 . ?
C00H C007 1.412(3) . ?
C00I H00J 0.9500 . ?
C002 C006 1.429(3) . ?
C002 C007 1.423(2) . ?
C003 H003 0.9500 . ?
C003 C005 1.384(2) . ?
C003 C009 1.399(2) . ?
C005 H005 0.9500 . ?
C006 C009 1.484(2) . ?
C008 H008 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
C008 N001 C002 118.21(15) . . ?
C00G C00A C00J 120.48(17) . . ?
C00G C00A C005 118.65(17) . . ?
C005 C00A C00J 120.86(18) . . ?
C00G C00B H00B 119.4 . . ?
C00G C00B C009 121.13(16) . . ?
C009 C00B H00B 119.4 . . ?
C00I C00C H00C 119.1 . . ?
C006 C00C H00C 119.1 . . ?
C006 C00C C00I 121.85(19) . . ?
C00H C00D H00D 120.7 . . ?
C00H C00D C008 118.59(17) . . ?
C008 C00D H00D 120.7 . . ?
C00I C00E H00E 119.8 . . ?
C00I C00E C007 120.37(18) . . ?
C007 C00E H00E 119.8 . . ?
H00A C00F H00F 109.5 . . ?
H00A C00F H00G 109.5 . . ?
H00F C00F H00G 109.5 . . ?
C00J C00F H00A 109.5 . . ?
C00J C00F H00F 109.5 . . ?
C00J C00F H00G 109.5 . . ?
C00A C00G H00H 119.8 . . ?
C00B C00G C00A 120.33(17) . . ?
C00B C00G H00H 119.8 . . ?
C00D C00H H00I 120.1 . . ?
C00D C00H C007 119.74(17) . . ?
C007 C00H H00I 120.1 . . ?
C00C C00I H00J 119.8 . . ?
C00E C00I C00C 120.31(17) . . ?
C00E C00I H00J 119.8 . . ?
O004 C00J C00A 119.3(2) . . ?
O004 C00J C00F 121.7(2) . . ?
C00F C00J C00A 118.94(19) . . ?
N001 C002 C006 119.11(15) . . ?
N001 C002 C007 121.58(16) . . ?
C007 C002 C006 119.29(16) . . ?
C005 C003 H003 119.7 . . ?
C005 C003 C009 120.58(16) . . ?
C009 C003 H003 119.7 . . ?
C00A C005 H005 119.5 . . ?
C003 C005 C00A 121.09(16) . . ?
C003 C005 H005 119.5 . . ?
C00C C006 C002 118.52(17) . . ?
C00C C006 C009 119.04(17) . . ?
C002 C006 C009 122.43(15) . . ?
C00E C007 C002 119.65(18) . . ?
C00H C007 C00E 122.44(18) . . ?
C00H C007 C002 117.90(16) . . ?
N001 C008 C00D 123.97(16) . . ?
N001 C008 H008 118.0 . . ?
C00D C008 H008 118.0 . . ?
C00B C009 C006 119.36(15) . . ?
C003 C009 C00B 118.21(16) . . ?
C003 C009 C006 122.40(15) . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.828
_oxdiff_exptl_absorpt_empirical_full_min 0.736
####################################################################### 
# 
# 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_fww-w1-100k
_database_code_depnum_ccdc_archive 'CCDC 2111663'
loop_
_audit_author_name
_audit_author_address
'Long-jie Wang'
;Yunnan university
China
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 N2 O S'
_chemical_formula_sum            'C14 H10 N2 O S'
_chemical_formula_weight         254.30
_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 0.0033 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'
S S 0.1246 0.1234 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   3.8241(2)
_cell_length_b                   21.5934(8)
_cell_length_c                   13.7628(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.180(3)
_cell_angle_gamma                90
_cell_volume                     1133.44(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3572
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.6870
_cell_measurement_theta_min      1.7430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7196
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.164
_diffrn_reflns_theta_min         1.758
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  16.00   0.50    0.40    --  -11.46 -99.00 -60.00   52
  2  ω      6.00  33.00   0.50    0.40    --  -11.46 -99.00 -90.00   54
  3  ω    -10.00  34.00   0.50    0.40    --  -11.46 -99.00 -30.00   88
  4  ω    -64.00  39.00   0.50    0.40    --   10.36 -81.00 133.00  206
  5  ω    -10.00  59.00   0.50    0.40    --   10.36  81.00-104.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0920517000
_diffrn_orient_matrix_UB_12      0.0275159000
_diffrn_orient_matrix_UB_13      -0.0099976000
_diffrn_orient_matrix_UB_21      -0.1287938000
_diffrn_orient_matrix_UB_22      0.0071847000
_diffrn_orient_matrix_UB_23      -0.0380449000
_diffrn_orient_matrix_UB_31      -0.0977856000
_diffrn_orient_matrix_UB_32      0.0164032000
_diffrn_orient_matrix_UB_33      0.0335136000
_diffrn_oxdiff_digest_frames     
;
01e7b8aad085457e197d333e061e47c740005382aae
;
_diffrn_oxdiff_digest_hkl        
;
0103f5ec0571c43c607a06b0daa8958d2fa013
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2029
_reflns_number_total             2475
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_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         0.312
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1332
_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:
 C008(H008), C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00H(H00H),
 C00I(H00I)
2.b Idealised Me refined as rotating group:
 C00G(H00B,H00E,H00F)
;
_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
S01 S 0.52900(13) 0.14894(2) 0.59093(3) 0.02216(19) Uani 1 1 d . . . . .
O002 O 0.9966(4) 0.55218(5) 0.73768(10) 0.0248(3) Uani 1 1 d . . . . .
N003 N 0.5735(4) 0.22299(6) 0.60186(11) 0.0176(3) Uani 1 1 d . . . . .
N004 N 0.3214(4) 0.14378(7) 0.48485(11) 0.0215(4) Uani 1 1 d . . . . .
C005 C 0.5195(5) 0.36128(7) 0.56641(13) 0.0142(4) Uani 1 1 d . . . . .
C006 C 0.7298(5) 0.45572(7) 0.69879(12) 0.0144(4) Uani 1 1 d . . . . .
C007 C 0.3956(5) 0.31288(7) 0.49617(12) 0.0145(4) Uani 1 1 d . . . . .
C008 C 0.6649(5) 0.41667(8) 0.53392(12) 0.0160(4) Uani 1 1 d . . . . .
H008 H 0.691651 0.422507 0.466452 0.019 Uiso 1 1 calc R . . . .
C009 C 0.7691(5) 0.46267(7) 0.59955(13) 0.0161(4) Uani 1 1 d . . . . .
H009 H 0.869241 0.499669 0.576602 0.019 Uiso 1 1 calc R . . . .
C00A C 0.5798(5) 0.40129(7) 0.73129(12) 0.0151(4) Uani 1 1 d . . . . .
H00A H 0.546130 0.396166 0.798524 0.018 Uiso 1 1 calc R . . . .
C00B C 0.4192(5) 0.24795(7) 0.51986(12) 0.0153(4) Uani 1 1 d . . . . .
C00C C 0.4796(5) 0.35459(7) 0.66569(12) 0.0150(4) Uani 1 1 d . . . . .
H00C H 0.382052 0.317423 0.688908 0.018 Uiso 1 1 calc R . . . .
C00D C 0.2409(5) 0.32740(8) 0.40595(12) 0.0177(4) Uani 1 1 d . . . . .
H00D H 0.227911 0.369685 0.386978 0.021 Uiso 1 1 calc R . . . .
C00E C 0.2756(5) 0.20260(8) 0.45212(13) 0.0176(4) Uani 1 1 d . . . . .
C00F C 0.8589(5) 0.50549(7) 0.76763(13) 0.0177(4) Uani 1 1 d . . . . .
C00G C 0.8268(5) 0.49618(7) 0.87481(13) 0.0209(4) Uani 1 1 d . . . . .
H00B H 0.958610 0.459191 0.896660 0.031 Uiso 1 1 calc GR . . . .
H00E H 0.579340 0.490871 0.887044 0.031 Uiso 1 1 calc GR . . . .
H00F H 0.921582 0.532416 0.910625 0.031 Uiso 1 1 calc GR . . . .
C00H C 0.0989(5) 0.28171(8) 0.33949(12) 0.0190(4) Uani 1 1 d . . . . .
H00H H -0.004896 0.294513 0.277946 0.023 Uiso 1 1 calc R . . . .
C00I C 0.1078(5) 0.22041(8) 0.36164(13) 0.0202(4) Uani 1 1 d . . . . .
H00I H 0.004580 0.190525 0.317748 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S01 N003 1.6140(15) . ?
S01 N004 1.6140(17) . ?
O002 C00F 1.223(2) . ?
N003 C00B 1.347(2) . ?
N004 C00E 1.355(2) . ?
C005 C007 1.478(2) . ?
C005 C008 1.406(2) . ?
C005 C00C 1.393(2) . ?
C006 C009 1.393(2) . ?
C006 C00A 1.396(2) . ?
C006 C00F 1.493(2) . ?
C007 C00B 1.441(2) . ?
C007 C00D 1.372(2) . ?
C008 C009 1.382(2) . ?
C00A C00C 1.389(2) . ?
C00B C00E 1.434(2) . ?
C00D C00H 1.426(3) . ?
C00E C00I 1.412(3) . ?
C00F C00G 1.503(2) . ?
C00H C00I 1.358(3) . ?

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
N003 S01 N004 101.20(8) . . ?
C00B N003 S01 106.35(12) . . ?
C00E N004 S01 106.21(12) . . ?
C008 C005 C007 120.60(15) . . ?
C00C C005 C007 121.01(15) . . ?
C00C C005 C008 118.32(16) . . ?
C009 C006 C00A 118.75(15) . . ?
C009 C006 C00F 119.38(15) . . ?
C00A C006 C00F 121.84(15) . . ?
C00B C007 C005 121.89(16) . . ?
C00D C007 C005 121.78(15) . . ?
C00D C007 C00B 116.29(15) . . ?
C009 C008 C005 120.38(16) . . ?
C008 C009 C006 121.13(15) . . ?
C00C C00A C006 120.24(15) . . ?
N003 C00B C007 126.53(16) . . ?
N003 C00B C00E 113.26(15) . . ?
C00E C00B C007 120.19(16) . . ?
C00A C00C C005 121.16(15) . . ?
C007 C00D C00H 122.77(16) . . ?
N004 C00E C00B 112.97(16) . . ?
N004 C00E C00I 126.01(16) . . ?
C00I C00E C00B 121.02(15) . . ?
O002 C00F C006 120.68(16) . . ?
O002 C00F C00G 120.61(16) . . ?
C006 C00F C00G 118.68(14) . . ?
C00I C00H C00D 121.89(17) . . ?
C00H C00I C00E 117.76(16) . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.586
####################################################################### 
# 
# 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_fww1-nolabel-colorless-plate-300k
_database_code_depnum_ccdc_archive 'CCDC 2111665'
loop_
_audit_author_name
_audit_author_address
'Long-jie Wang'
;Yunnan university
China
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N O'
_chemical_formula_sum            'C16 H11 N O'
_chemical_formula_weight         233.26
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.7848(8)
_cell_length_b                   7.4289(4)
_cell_length_c                   14.9066(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.205(7)
_cell_angle_gamma                90
_cell_volume                     1187.31(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3554
_cell_measurement_temperature    300.92(10)
_cell_measurement_theta_max      29.2370
_cell_measurement_theta_min      1.8820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.788
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7687
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.372
_diffrn_reflns_theta_min         1.899
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.92(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.788
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  57.00   0.50    0.48    --  -11.46  64.00 112.00  194
  2  ω      4.00  34.00   0.50    0.48    --  -11.46 -99.00 120.00   60
  3  ω    -82.00  10.00   0.50    0.48    --  -11.46 -64.00 -23.00  184
  4  ω    -11.00  17.00   0.50    0.48    --  -11.46 -99.00-150.00   56
  5  ω    -10.00  16.00   0.50    0.48    --  -11.46 -99.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0517313000
_diffrn_orient_matrix_UB_12      -0.0511457000
_diffrn_orient_matrix_UB_13      -0.0110493000
_diffrn_orient_matrix_UB_21      -0.0398272000
_diffrn_orient_matrix_UB_22      -0.0499598000
_diffrn_orient_matrix_UB_23      -0.0317856000
_diffrn_orient_matrix_UB_31      0.0103620000
_diffrn_orient_matrix_UB_32      0.0633143000
_diffrn_orient_matrix_UB_33      -0.0340711000
_diffrn_oxdiff_digest_frames     
;
01b0b83c3c5c1398596b54958988b4b664005465729
;
_diffrn_oxdiff_digest_hkl        
;
01aa6a2e2e988011432474118deff6ce33d7e1
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1621
_reflns_number_total             2570
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_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         0.109
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+0.0429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C009, C00I
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
3.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I)
;
_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
N001 N 0.21530(11) 0.48540(15) 0.27226(8) 0.0566(3) Uani 1 1 d . . . . .
C002 C 0.20118(13) 0.63669(17) 0.21989(9) 0.0516(4) Uani 1 1 d . . . . .
O003 O 0.76180(14) 0.8236(2) 0.54642(9) 0.1041(5) Uani 1 1 d . . . . .
C004 C 0.28334(14) 0.78540(17) 0.24145(10) 0.0542(4) Uani 1 1 d . . . . .
C005 C 0.37817(14) 0.78377(17) 0.32149(10) 0.0530(4) Uani 1 1 d . . . . .
C006 C 0.10925(14) 0.64811(19) 0.14460(10) 0.0577(4) Uani 1 1 d . . . . .
C007 C 0.34990(15) 0.72619(19) 0.40587(10) 0.0608(4) Uani 1 1 d . . . . .
H007 H 0.269941 0.685265 0.412620 0.073 Uiso 1 1 calc R . . . .
C008 C 0.49877(14) 0.84751(18) 0.31482(10) 0.0596(4) Uani 1 1 d . . . . .
H008 H 0.519371 0.889829 0.259617 0.072 Uiso 1 1 calc R . . . .
C009 C 0.55877(14) 0.78797(18) 0.47133(10) 0.0576(4) Uani 1 1 d . U . . .
C00A C 0.58745(15) 0.84883(19) 0.38830(11) 0.0613(4) Uani 1 1 d . . . . .
H00A H 0.667314 0.890918 0.382189 0.074 Uiso 1 1 calc R . . . .
C00B C 0.43897(15) 0.72915(19) 0.47946(10) 0.0624(4) Uani 1 1 d . . . . .
H00B H 0.418169 0.691048 0.535350 0.075 Uiso 1 1 calc R . . . .
C00C C 0.13779(15) 0.3510(2) 0.25202(11) 0.0639(4) Uani 1 1 d . . . . .
H00C H 0.147014 0.248070 0.287644 0.077 Uiso 1 1 calc R . . . .
C00D C 0.02849(15) 0.4997(2) 0.12703(11) 0.0666(4) Uani 1 1 d . . . . .
H00D H -0.034007 0.503202 0.078912 0.080 Uiso 1 1 calc R . . . .
C00E C 0.27157(16) 0.9333(2) 0.18598(11) 0.0663(4) Uani 1 1 d . . . . .
H00E H 0.325245 1.030177 0.198618 0.080 Uiso 1 1 calc R . . . .
C00F C 0.04244(15) 0.3526(2) 0.18048(11) 0.0677(4) Uani 1 1 d . . . . .
H00F H -0.010394 0.254151 0.169899 0.081 Uiso 1 1 calc R . . . .
C00G C 0.10159(17) 0.8048(2) 0.09113(11) 0.0711(5) Uani 1 1 d . . . . .
H00G H 0.041204 0.813310 0.041822 0.085 Uiso 1 1 calc R . . . .
C00H C 0.18160(18) 0.9434(2) 0.11104(12) 0.0759(5) Uani 1 1 d . . . . .
H00H H 0.176719 1.045623 0.074788 0.091 Uiso 1 1 calc R . . . .
C00I C 0.65446(18) 0.7855(2) 0.54878(12) 0.0743(5) Uani 1 1 d . U . . .
H00I H 0.629857 0.751649 0.604252 0.089 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C002 1.3675(17) . ?
N001 C00C 1.3162(18) . ?
C002 C004 1.4308(19) . ?
C002 C006 1.418(2) . ?
O003 C00I 1.196(2) . ?
C004 C005 1.485(2) . ?
C004 C00E 1.373(2) . ?
C005 C007 1.3932(19) . ?
C005 C008 1.398(2) . ?
C006 C00D 1.412(2) . ?
C006 C00G 1.408(2) . ?
C007 C00B 1.378(2) . ?
C008 C00A 1.374(2) . ?
C009 C00A 1.384(2) . ?
C009 C00B 1.382(2) . ?
C009 C00I 1.463(2) . ?
C00C C00F 1.399(2) . ?
C00D C00F 1.351(2) . ?
C00E C00H 1.400(2) . ?
C00G C00H 1.355(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C N001 C002 117.64(13) . . ?
N001 C002 C004 118.58(13) . . ?
N001 C002 C006 121.76(13) . . ?
C006 C002 C004 119.65(12) . . ?
C002 C004 C005 122.01(11) . . ?
C00E C004 C002 117.91(14) . . ?
C00E C004 C005 120.08(13) . . ?
C007 C005 C004 121.94(13) . . ?
C007 C005 C008 117.67(14) . . ?
C008 C005 C004 120.35(12) . . ?
C00D C006 C002 117.70(13) . . ?
C00G C006 C002 119.39(14) . . ?
C00G C006 C00D 122.91(15) . . ?
C00B C007 C005 120.80(14) . . ?
C00A C008 C005 121.24(13) . . ?
C00A C009 C00I 120.20(15) . . ?
C00B C009 C00A 118.91(15) . . ?
C00B C009 C00I 120.89(14) . . ?
C008 C00A C009 120.47(14) . . ?
C007 C00B C009 120.88(14) . . ?
N001 C00C C00F 124.36(14) . . ?
C00F C00D C006 119.67(15) . . ?
C004 C00E C00H 122.31(15) . . ?
C00D C00F C00C 118.82(14) . . ?
C00H C00G C006 120.47(15) . . ?
C00G C00H C00E 120.24(15) . . ?
O003 C00I C009 125.19(17) . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.714
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2111661'
loop_
_audit_author_name
_audit_author_address
'Long-jie Wang'
;Yunnan university
China
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.2612(10)
_cell_length_b                   7.3739(8)
_cell_length_c                   15.4845(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.600(4)
_cell_angle_gamma                90
_cell_volume                     1284.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2069
_cell_measurement_temperature    193
_cell_measurement_theta_max      75.818
_cell_measurement_theta_min      3.530
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1603 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.8089.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11175
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.633
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1800
_reflns_number_total             2947
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.022
_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)+(0.0414P)²+0.4349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1416
_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), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.49056(14) -0.1546(2) 0.34344(10) 0.0466(4) Uani 1 1 d . . . . .
N1 N 0.87587(16) 0.5521(3) 0.78094(12) 0.0447(5) Uani 1 1 d . . . . .
C1 C 0.79051(19) 0.4364(3) 0.74841(14) 0.0411(6) Uani 1 1 d . . . . .
H1 H 0.750042 0.363929 0.788400 0.049 Uiso 1 1 calc R . . . .
C2 C 0.75902(18) 0.4171(3) 0.66335(13) 0.0342(5) Uani 1 1 d . . . . .
H2 H 0.698410 0.333843 0.645415 0.041 Uiso 1 1 calc R . . . .
C3 C 0.81748(17) 0.5224(3) 0.60131(13) 0.0323(5) Uani 1 1 d . . . . .
C4 C 0.90498(17) 0.6461(3) 0.63353(13) 0.0337(5) Uani 1 1 d . . . . .
C5 C 0.92938(19) 0.6508(3) 0.72373(14) 0.0412(6) Uani 1 1 d . . . . .
H5 H 0.989460 0.731938 0.744804 0.049 Uiso 1 1 calc R . . . .
C6 C 0.96307(19) 0.7621(3) 0.57598(14) 0.0408(6) Uani 1 1 d . . . . .
H6 H 1.023814 0.841954 0.597270 0.049 Uiso 1 1 calc R . . . .
C7 C 0.9316(2) 0.7589(3) 0.49012(15) 0.0447(6) Uani 1 1 d . . . . .
H7 H 0.968202 0.839962 0.451779 0.054 Uiso 1 1 calc R . . . .
C8 C 0.8451(2) 0.6359(3) 0.45795(14) 0.0405(5) Uani 1 1 d . . . . .
H8 H 0.824785 0.635103 0.397731 0.049 Uiso 1 1 calc R . . . .
C9 C 0.78896(18) 0.5169(3) 0.51085(13) 0.0335(5) Uani 1 1 d . . . . .
C10 C 0.70147(18) 0.3847(3) 0.47285(13) 0.0337(5) Uani 1 1 d . . . . .
C11 C 0.71659(18) 0.1975(3) 0.48381(13) 0.0351(5) Uani 1 1 d . . . . .
H11 H 0.781306 0.153347 0.519279 0.042 Uiso 1 1 calc R . . . .
C12 C 0.63862(18) 0.0762(3) 0.44371(13) 0.0343(5) Uani 1 1 d . . . . .
H12 H 0.650866 -0.050399 0.451097 0.041 Uiso 1 1 calc R . . . .
C13 C 0.54218(17) 0.1382(3) 0.39252(12) 0.0323(5) Uani 1 1 d . . . . .
C14 C 0.52573(18) 0.3244(3) 0.38326(14) 0.0374(5) Uani 1 1 d . . . . .
H14 H 0.459197 0.368614 0.349696 0.045 Uiso 1 1 calc R . . . .
C15 C 0.60494(18) 0.4459(3) 0.42225(13) 0.0379(5) Uani 1 1 d . . . . .
H15 H 0.593070 0.572475 0.414273 0.045 Uiso 1 1 calc R . . . .
C16 C 0.46265(19) 0.0046(3) 0.34673(13) 0.0362(5) Uani 1 1 d . . . . .
C17 C 0.3480(2) 0.0710(3) 0.30480(16) 0.0487(6) Uani 1 1 d . . . . .
H17A H 0.364982 0.159313 0.259719 0.073 Uiso 1 1 calc GR . . . .
H17B H 0.300106 0.128639 0.348389 0.073 Uiso 1 1 calc GR . . . .
H17C H 0.304080 -0.031693 0.278926 0.073 Uiso 1 1 calc GR . . . .


_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 C16 1.217(3) . ?
N1 C1 1.364(3) . ?
N1 C5 1.314(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.356(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.420(3) . ?
C3 C4 1.417(3) . ?
C3 C9 1.423(3) . ?
C4 C5 1.412(3) . ?
C4 C6 1.417(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.361(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.405(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(3) . ?
C9 C10 1.488(3) . ?
C10 C11 1.400(3) . ?
C10 C15 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
C13 C14 1.392(3) . ?
C13 C16 1.490(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.501(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C5 N1 C1 115.74(19) . . ?
N1 C1 H1 117.5 . . ?
C2 C1 N1 125.0(2) . . ?
C2 C1 H1 117.5 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C9 124.0(2) . . ?
C4 C3 C2 116.77(19) . . ?
C4 C3 C9 119.14(19) . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C6 122.2(2) . . ?
C6 C4 C3 120.07(19) . . ?
N1 C5 C4 125.4(2) . . ?
N1 C5 H5 117.3 . . ?
C4 C5 H5 117.3 . . ?
C4 C6 H6 120.1 . . ?
C7 C6 C4 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.1(2) . . ?
C9 C8 H8 119.0 . . ?
C3 C9 C10 121.56(19) . . ?
C8 C9 C3 118.6(2) . . ?
C8 C9 C10 119.80(19) . . ?
C11 C10 C9 121.56(19) . . ?
C15 C10 C9 119.9(2) . . ?
C15 C10 C11 118.5(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C16 119.4(2) . . ?
C14 C13 C12 118.6(2) . . ?
C14 C13 C16 121.95(19) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
O1 C16 C13 120.5(2) . . ?
O1 C16 C17 121.0(2) . . ?
C13 C16 C17 118.5(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
N1 C1 C2 C3 0.2(3) . . . . ?
C1 N1 C5 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C1 C2 C3 C9 -178.0(2) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C2 C3 C4 C6 -176.96(19) . . . . ?
C2 C3 C9 C8 174.7(2) . . . . ?
C2 C3 C9 C10 -6.0(3) . . . . ?
C3 C4 C5 N1 -1.5(3) . . . . ?
C3 C4 C6 C7 2.3(3) . . . . ?
C3 C9 C10 C11 -57.9(3) . . . . ?
C3 C9 C10 C15 124.9(2) . . . . ?
C4 C3 C9 C8 -1.8(3) . . . . ?
C4 C3 C9 C10 177.46(19) . . . . ?
C4 C6 C7 C8 -2.5(4) . . . . ?
C5 N1 C1 C2 0.4(3) . . . . ?
C5 C4 C6 C7 -176.5(2) . . . . ?
C6 C4 C5 N1 177.4(2) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
C7 C8 C9 C3 1.7(3) . . . . ?
C7 C8 C9 C10 -177.6(2) . . . . ?
C8 C9 C10 C11 121.4(2) . . . . ?
C8 C9 C10 C15 -55.8(3) . . . . ?
C9 C3 C4 C5 178.72(19) . . . . ?
C9 C3 C4 C6 -0.1(3) . . . . ?
C9 C10 C11 C12 -175.94(19) . . . . ?
C9 C10 C15 C14 177.1(2) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C11 C12 C13 C16 177.19(18) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C12 C13 C16 O1 -10.7(3) . . . . ?
C12 C13 C16 C17 169.5(2) . . . . ?
C13 C14 C15 C10 -1.2(3) . . . . ?
C14 C13 C16 O1 166.9(2) . . . . ?
C14 C13 C16 C17 -13.0(3) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
C16 C13 C14 C15 -176.04(19) . . . . ?

_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_fww-3
_database_code_depnum_ccdc_archive 'CCDC 2111734'
loop_
_audit_author_name
_audit_author_address
'Long-jie Wang'
;Yunnan university
China
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   17.7346(3)
_cell_length_b                   14.1145(2)
_cell_length_c                   16.7364(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.410(2)
_cell_angle_gamma                90
_cell_volume                     3814.89(12)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    12176
_cell_measurement_temperature    301.08(10)
_cell_measurement_theta_max      75.6990
_cell_measurement_theta_min      2.7250
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76307
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24965
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.908
_diffrn_reflns_theta_min         2.736
_diffrn_ambient_temperature      301.08(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6065
_reflns_number_total             7728
_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 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7728
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0902P)²+0.3272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1564
_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), C3(H3), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C28(H28),
  C29(H29), C31(H31), C32(H32), C35(H35), C36(H36), C37(H37), C40(H40),
 C41(H41), C42(H42), C45(H45), C46(H46), C48(H48), C49(H49)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C), C51(H51A,H51B,H51C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.65580(6) 0.64934(8) 0.51082(7) 0.0711(3) Uani 1 1 d . . . . .
N1 N 1.03586(7) 0.59140(8) 1.11430(7) 0.0585(3) Uani 1 1 d . . . . .
C1 C 0.96413(9) 0.56438(10) 1.11139(9) 0.0613(4) Uani 1 1 d . . . . .
H1 H 0.962981 0.536953 1.161403 0.074 Uiso 1 1 calc R . . . .
C2 C 0.88880(9) 0.57434(10) 1.03723(9) 0.0574(3) Uani 1 1 d . . . . .
H2 H 0.839509 0.554536 1.039040 0.069 Uiso 1 1 calc R . . . .
C3 C 0.88861(8) 0.61324(9) 0.96268(8) 0.0499(3) Uani 1 1 d . . . . .
H3 H 0.839193 0.620459 0.913169 0.060 Uiso 1 1 calc R . . . .
C4 C 0.96423(7) 0.64252(8) 0.96134(7) 0.0436(3) Uani 1 1 d . . . . .
C5 C 1.03701(7) 0.63161(9) 1.04025(8) 0.0479(3) Uani 1 1 d . . . . .
C6 C 1.11326(8) 0.66604(10) 1.04436(9) 0.0548(3) Uani 1 1 d . . . . .
H6 H 1.161336 0.657470 1.095134 0.066 Uiso 1 1 calc R . . . .
C7 C 1.11673(8) 0.71168(10) 0.97440(9) 0.0551(3) Uani 1 1 d . . . . .
H7 H 1.166779 0.736624 0.978624 0.066 Uiso 1 1 calc R . . . .
C8 C 1.04526(8) 0.72153(9) 0.89562(8) 0.0520(3) Uani 1 1 d . . . . .
H8 H 1.048932 0.752752 0.848426 0.062 Uiso 1 1 calc R . . . .
C9 C 0.97042(7) 0.68602(8) 0.88713(8) 0.0455(3) Uani 1 1 d . . . . .
C10 C 0.89716(7) 0.69457(8) 0.80147(8) 0.0449(3) Uani 1 1 d . . . . .
C11 C 0.87286(8) 0.78298(9) 0.76292(8) 0.0513(3) Uani 1 1 d . . . . .
H11 H 0.901370 0.836852 0.791748 0.062 Uiso 1 1 calc R . . . .
C12 C 0.80649(8) 0.79158(9) 0.68186(8) 0.0513(3) Uani 1 1 d . . . . .
H12 H 0.790733 0.851323 0.657118 0.062 Uiso 1 1 calc R . . . .
C13 C 0.76327(7) 0.71248(8) 0.63716(8) 0.0457(3) Uani 1 1 d . . . . .
C14 C 0.78785(8) 0.62364(9) 0.67543(8) 0.0502(3) Uani 1 1 d . . . . .
H14 H 0.759592 0.569841 0.646156 0.060 Uiso 1 1 calc R . . . .
C15 C 0.85383(8) 0.61460(9) 0.75651(8) 0.0502(3) Uani 1 1 d . . . . .
H15 H 0.869468 0.554843 0.781263 0.060 Uiso 1 1 calc R . . . .
C16 C 0.69132(8) 0.71969(10) 0.54951(8) 0.0516(3) Uani 1 1 d . . . . .
C17 C 0.66321(10) 0.81529(12) 0.51006(11) 0.0777(5) Uani 1 1 d . . . . .
H17A H 0.617681 0.808336 0.453714 0.117 Uiso 1 1 calc GR . . . .
H17B H 0.708054 0.847112 0.503292 0.117 Uiso 1 1 calc GR . . . .
H17C H 0.645840 0.851825 0.547840 0.117 Uiso 1 1 calc GR . . . .
O2 O 0.31554(7) 0.32879(8) 0.18315(7) 0.0756(3) Uani 1 1 d . . . . .
N2 N 0.70581(8) 0.24861(9) 0.78011(7) 0.0633(3) Uani 1 1 d . . . . .
C18 C 0.63414(10) 0.22569(11) 0.77964(10) 0.0683(4) Uani 1 1 d . . . . .
H18 H 0.633914 0.197558 0.829784 0.082 Uiso 1 1 calc R . . . .
C19 C 0.55760(10) 0.24073(11) 0.70853(10) 0.0636(4) Uani 1 1 d . . . . .
H19 H 0.508490 0.224489 0.712617 0.076 Uiso 1 1 calc R . . . .
C20 C 0.55628(8) 0.27954(9) 0.63332(9) 0.0527(3) Uani 1 1 d . . . . .
H20 H 0.506193 0.289981 0.585424 0.063 Uiso 1 1 calc R . . . .
C21 C 0.63168(7) 0.30368(8) 0.62892(8) 0.0451(3) Uani 1 1 d . . . . .
C22 C 0.70595(8) 0.28886(9) 0.70564(8) 0.0504(3) Uani 1 1 d . . . . .
C23 C 0.78211(8) 0.31931(10) 0.70677(9) 0.0577(3) Uani 1 1 d . . . . .
H23 H 0.830841 0.308917 0.756396 0.069 Uiso 1 1 calc R . . . .
C24 C 0.78498(8) 0.36365(10) 0.63612(10) 0.0581(3) Uani 1 1 d . . . . .
H24 H 0.835337 0.385568 0.638547 0.070 Uiso 1 1 calc R . . . .
C25 C 0.71217(8) 0.37673(10) 0.55907(9) 0.0544(3) Uani 1 1 d . . . . .
H25 H 0.715237 0.406653 0.510994 0.065 Uiso 1 1 calc R . . . .
C26 C 0.63687(7) 0.34604(9) 0.55384(8) 0.0463(3) Uani 1 1 d . . . . .
C27 C 0.56164(7) 0.35928(8) 0.47054(7) 0.0450(3) Uani 1 1 d . . . . .
C28 C 0.54130(8) 0.44905(9) 0.43393(8) 0.0514(3) Uani 1 1 d . . . . .
H28 H 0.574137 0.500644 0.462118 0.062 Uiso 1 1 calc R . . . .
C29 C 0.47238(8) 0.46229(9) 0.35566(8) 0.0518(3) Uani 1 1 d . . . . .
H29 H 0.458821 0.522936 0.332390 0.062 Uiso 1 1 calc R . . . .
C30 C 0.42343(7) 0.38616(9) 0.31167(8) 0.0458(3) Uani 1 1 d . . . . .
C31 C 0.44385(8) 0.29602(9) 0.34826(8) 0.0489(3) Uani 1 1 d . . . . .
H31 H 0.411351 0.244400 0.319553 0.059 Uiso 1 1 calc R . . . .
C32 C 0.51189(8) 0.28261(9) 0.42677(8) 0.0493(3) Uani 1 1 d . . . . .
H32 H 0.524684 0.222132 0.450651 0.059 Uiso 1 1 calc R . . . .
C33 C 0.35082(8) 0.39732(10) 0.22554(9) 0.0526(3) Uani 1 1 d . . . . .
C34 C 0.32122(10) 0.49478(12) 0.19118(12) 0.0814(5) Uani 1 1 d . . . . .
H34A H 0.273888 0.490035 0.135975 0.122 Uiso 1 1 calc GR . . . .
H34B H 0.364644 0.528437 0.183202 0.122 Uiso 1 1 calc GR . . . .
H34C H 0.306163 0.528264 0.232355 0.122 Uiso 1 1 calc GR . . . .
O3 O -0.00835(7) -0.00988(8) -0.16387(7) 0.0758(3) Uani 1 1 d . . . . .
N3 N 0.37169(8) -0.06744(9) 0.44220(7) 0.0637(3) Uani 1 1 d . . . . .
C35 C 0.30023(10) -0.09324(11) 0.44083(9) 0.0638(4) Uani 1 1 d . . . . .
H35 H 0.300156 -0.121387 0.491044 0.077 Uiso 1 1 calc R . . . .
C36 C 0.22379(9) -0.08132(10) 0.36885(9) 0.0569(3) Uani 1 1 d . . . . .
H36 H 0.174865 -0.099500 0.372411 0.068 Uiso 1 1 calc R . . . .
C37 C 0.22235(8) -0.04283(9) 0.29385(8) 0.0493(3) Uani 1 1 d . . . . .
H37 H 0.172245 -0.034407 0.245451 0.059 Uiso 1 1 calc R . . . .
C38 C 0.29738(7) -0.01563(8) 0.28972(8) 0.0454(3) Uani 1 1 d . . . . .
C39 C 0.37133(8) -0.02724(9) 0.36742(8) 0.0523(3) Uani 1 1 d . . . . .
C40 C 0.44718(8) 0.00539(11) 0.36909(9) 0.0633(4) Uani 1 1 d . . . . .
H40 H 0.495837 -0.002552 0.419356 0.076 Uiso 1 1 calc R . . . .
C41 C 0.44923(8) 0.04840(12) 0.29734(10) 0.0646(4) Uani 1 1 d . . . . .
H41 H 0.499197 0.071625 0.299734 0.078 Uiso 1 1 calc R . . . .
C42 C 0.37683(8) 0.05833(11) 0.21941(9) 0.0577(3) Uani 1 1 d . . . . .
H42 H 0.379866 0.087102 0.170838 0.069 Uiso 1 1 calc R . . . .
C43 C 0.30206(7) 0.02623(9) 0.21415(8) 0.0475(3) Uani 1 1 d . . . . .
C44 C 0.22761(7) 0.03511(9) 0.12974(8) 0.0450(3) Uani 1 1 d . . . . .
C45 C 0.20632(8) 0.12302(9) 0.08924(8) 0.0515(3) Uani 1 1 d . . . . .
H45 H 0.237349 0.176174 0.116323 0.062 Uiso 1 1 calc R . . . .
C46 C 0.13915(8) 0.13218(9) 0.00875(8) 0.0511(3) Uani 1 1 d . . . . .
H46 H 0.125153 0.191594 -0.017248 0.061 Uiso 1 1 calc R . . . .
C47 C 0.09263(7) 0.05371(8) -0.03339(7) 0.0444(3) Uani 1 1 d . . . . .
C48 C 0.11353(7) -0.03432(8) 0.00769(8) 0.0476(3) Uani 1 1 d . . . . .
H48 H 0.082392 -0.087380 -0.019470 0.057 Uiso 1 1 calc R . . . .
C49 C 0.17987(8) -0.04375(9) 0.08818(8) 0.0488(3) Uani 1 1 d . . . . .
H49 H 0.192852 -0.102913 0.114884 0.059 Uiso 1 1 calc R . . . .
C50 C 0.02215(8) 0.06051(9) -0.12156(8) 0.0508(3) Uani 1 1 d . . . . .
C51 C -0.01083(9) 0.15642(11) -0.15685(10) 0.0678(4) Uani 1 1 d . . . . .
H51A H -0.055819 0.149885 -0.213635 0.102 Uiso 1 1 calc GR . . . .
H51B H 0.032357 0.193616 -0.161809 0.102 Uiso 1 1 calc GR . . . .
H51C H -0.030183 0.187300 -0.117755 0.102 Uiso 1 1 calc GR . . . .


_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 C16 1.2103(16) . ?
N1 C1 1.3095(19) . ?
N1 C5 1.3709(16) . ?
C1 H1 0.9300 . ?
C1 C2 1.405(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3619(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.4123(17) . ?
C4 C5 1.4230(16) . ?
C4 C9 1.4298(16) . ?
C5 C6 1.4116(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.360(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.4082(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.3700(17) . ?
C9 C10 1.4895(16) . ?
C10 C11 1.3890(17) . ?
C10 C15 1.3975(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3860(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3856(17) . ?
C13 C14 1.3935(17) . ?
C13 C16 1.4977(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3837(17) . ?
C15 H15 0.9300 . ?
C16 C17 1.494(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O2 C33 1.2098(16) . ?
N2 C18 1.308(2) . ?
N2 C22 1.3706(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.403(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.3641(18) . ?
C20 H20 0.9300 . ?
C20 C21 1.4109(17) . ?
C21 C22 1.4247(17) . ?
C21 C26 1.4284(16) . ?
C22 C23 1.4101(19) . ?
C23 H23 0.9300 . ?
C23 C24 1.357(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.4101(19) . ?
C25 H25 0.9300 . ?
C25 C26 1.3719(17) . ?
C26 C27 1.4904(16) . ?
C27 C28 1.3886(17) . ?
C27 C32 1.3971(16) . ?
C28 H28 0.9300 . ?
C28 C29 1.3861(17) . ?
C29 H29 0.9300 . ?
C29 C30 1.3863(17) . ?
C30 C31 1.3934(17) . ?
C30 C33 1.4922(17) . ?
C31 H31 0.9300 . ?
C31 C32 1.3813(17) . ?
C32 H32 0.9300 . ?
C33 C34 1.500(2) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O3 C50 1.2102(16) . ?
N3 C35 1.3097(19) . ?
N3 C39 1.3717(18) . ?
C35 H35 0.9300 . ?
C35 C36 1.403(2) . ?
C36 H36 0.9300 . ?
C36 C37 1.3582(18) . ?
C37 H37 0.9300 . ?
C37 C38 1.4138(17) . ?
C38 C39 1.4243(17) . ?
C38 C43 1.4290(17) . ?
C39 C40 1.411(2) . ?
C40 H40 0.9300 . ?
C40 C41 1.359(2) . ?
C41 H41 0.9300 . ?
C41 C42 1.4091(19) . ?
C42 H42 0.9300 . ?
C42 C43 1.3693(18) . ?
C43 C44 1.4876(16) . ?
C44 C45 1.3893(17) . ?
C44 C49 1.3975(16) . ?
C45 H45 0.9300 . ?
C45 C46 1.3871(17) . ?
C46 H46 0.9300 . ?
C46 C47 1.3870(16) . ?
C47 C48 1.3941(17) . ?
C47 C50 1.4915(17) . ?
C48 H48 0.9300 . ?
C48 C49 1.3809(16) . ?
C49 H49 0.9300 . ?
C50 C51 1.4959(19) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?

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
C1 N1 C5 117.66(12) . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 123.92(13) . . ?
C2 C1 H1 118.0 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.40(13) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.32(12) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 117.17(11) . . ?
C3 C4 C9 123.63(11) . . ?
C5 C4 C9 119.13(11) . . ?
N1 C5 C4 122.49(11) . . ?
N1 C5 C6 118.06(11) . . ?
C6 C5 C4 119.42(12) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.29(12) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.62(12) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.30(12) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C10 121.42(10) . . ?
C8 C9 C4 119.07(11) . . ?
C8 C9 C10 119.50(11) . . ?
C11 C10 C9 119.98(11) . . ?
C11 C10 C15 118.65(11) . . ?
C15 C10 C9 121.31(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.55(11) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.96(11) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 118.60(11) . . ?
C12 C13 C16 122.11(11) . . ?
C14 C13 C16 119.30(11) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.73(11) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.50(11) . . ?
C14 C15 H15 119.8 . . ?
O1 C16 C13 120.84(12) . . ?
O1 C16 C17 119.97(13) . . ?
C17 C16 C13 119.18(12) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 N2 C22 117.64(12) . . ?
N2 C18 H18 117.8 . . ?
N2 C18 C19 124.38(13) . . ?
C19 C18 H18 117.8 . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.01(13) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.34(13) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 117.43(11) . . ?
C20 C21 C26 123.64(11) . . ?
C22 C21 C26 118.85(11) . . ?
N2 C22 C21 122.13(12) . . ?
N2 C22 C23 118.42(12) . . ?
C23 C22 C21 119.41(12) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.63(12) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.48(12) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.09(12) . . ?
C26 C25 H25 119.5 . . ?
C21 C26 C27 121.14(10) . . ?
C25 C26 C21 119.41(11) . . ?
C25 C26 C27 119.44(11) . . ?
C28 C27 C26 119.74(11) . . ?
C28 C27 C32 118.87(11) . . ?
C32 C27 C26 121.37(11) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.45(11) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.76(12) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C31 118.84(11) . . ?
C29 C30 C33 122.15(11) . . ?
C31 C30 C33 118.99(11) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.62(11) . . ?
C32 C31 H31 119.7 . . ?
C27 C32 H32 119.8 . . ?
C31 C32 C27 120.45(11) . . ?
C31 C32 H32 119.8 . . ?
O2 C33 C30 120.85(12) . . ?
O2 C33 C34 119.62(13) . . ?
C30 C33 C34 119.53(12) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C35 N3 C39 117.35(12) . . ?
N3 C35 H35 117.8 . . ?
N3 C35 C36 124.50(13) . . ?
C36 C35 H35 117.8 . . ?
C35 C36 H36 120.5 . . ?
C37 C36 C35 118.95(13) . . ?
C37 C36 H36 120.5 . . ?
C36 C37 H37 120.2 . . ?
C36 C37 C38 119.68(12) . . ?
C38 C37 H37 120.2 . . ?
C37 C38 C39 117.01(11) . . ?
C37 C38 C43 123.76(11) . . ?
C39 C38 C43 119.17(11) . . ?
N3 C39 C38 122.42(12) . . ?
N3 C39 C40 118.16(12) . . ?
C40 C39 C38 119.41(12) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 C39 120.11(13) . . ?
C41 C40 H40 119.9 . . ?
C40 C41 H41 119.5 . . ?
C40 C41 C42 121.01(13) . . ?
C42 C41 H41 119.5 . . ?
C41 C42 H42 119.5 . . ?
C43 C42 C41 120.96(13) . . ?
C43 C42 H42 119.5 . . ?
C38 C43 C44 121.46(10) . . ?
C42 C43 C38 119.26(12) . . ?
C42 C43 C44 119.27(11) . . ?
C45 C44 C43 119.62(11) . . ?
C45 C44 C49 118.81(11) . . ?
C49 C44 C43 121.53(11) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 C44 120.55(11) . . ?
C46 C45 H45 119.7 . . ?
C45 C46 H46 119.6 . . ?
C47 C46 C45 120.73(11) . . ?
C47 C46 H46 119.6 . . ?
C46 C47 C48 118.68(11) . . ?
C46 C47 C50 122.07(11) . . ?
C48 C47 C50 119.25(11) . . ?
C47 C48 H48 119.6 . . ?
C49 C48 C47 120.85(11) . . ?
C49 C48 H48 119.6 . . ?
C44 C49 H49 119.8 . . ?
C48 C49 C44 120.36(11) . . ?
C48 C49 H49 119.8 . . ?
O3 C50 C47 121.01(12) . . ?
O3 C50 C51 120.31(12) . . ?
C47 C50 C51 118.68(11) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?

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
N1 C1 C2 C3 0.7(2) . . . . ?
N1 C5 C6 C7 -175.98(12) . . . . ?
C1 N1 C5 C4 -1.48(19) . . . . ?
C1 N1 C5 C6 176.33(12) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -1.65(18) . . . . ?
C2 C3 C4 C9 -178.54(12) . . . . ?
C3 C4 C5 N1 2.36(18) . . . . ?
C3 C4 C5 C6 -175.43(11) . . . . ?
C3 C4 C9 C8 172.69(11) . . . . ?
C3 C4 C9 C10 -6.50(18) . . . . ?
C4 C5 C6 C7 1.90(19) . . . . ?
C4 C9 C10 C11 123.53(13) . . . . ?
C4 C9 C10 C15 -59.27(16) . . . . ?
C5 N1 C1 C2 -0.1(2) . . . . ?
C5 C4 C9 C8 -4.14(17) . . . . ?
C5 C4 C9 C10 176.66(10) . . . . ?
C5 C6 C7 C8 -2.9(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C4 3.27(18) . . . . ?
C7 C8 C9 C10 -177.52(11) . . . . ?
C8 C9 C10 C11 -55.67(16) . . . . ?
C8 C9 C10 C15 121.53(13) . . . . ?
C9 C4 C5 N1 179.40(11) . . . . ?
C9 C4 C5 C6 1.61(17) . . . . ?
C9 C10 C11 C12 177.85(11) . . . . ?
C9 C10 C15 C14 -177.54(11) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C10 C15 C14 -0.30(18) . . . . ?
C11 C12 C13 C14 0.05(19) . . . . ?
C11 C12 C13 C16 179.99(11) . . . . ?
C12 C13 C14 C15 0.23(18) . . . . ?
C12 C13 C16 O1 178.23(13) . . . . ?
C12 C13 C16 C17 -2.07(19) . . . . ?
C13 C14 C15 C10 -0.10(19) . . . . ?
C14 C13 C16 O1 -1.83(19) . . . . ?
C14 C13 C16 C17 177.86(13) . . . . ?
C15 C10 C11 C12 0.58(18) . . . . ?
C16 C13 C14 C15 -179.71(11) . . . . ?
N2 C18 C19 C20 1.7(2) . . . . ?
N2 C22 C23 C24 -176.85(12) . . . . ?
C18 N2 C22 C21 -1.6(2) . . . . ?
C18 N2 C22 C23 176.18(13) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C19 C20 C21 C22 -2.12(18) . . . . ?
C19 C20 C21 C26 -178.92(12) . . . . ?
C20 C21 C22 N2 3.06(18) . . . . ?
C20 C21 C22 C23 -174.68(11) . . . . ?
C20 C21 C26 C25 172.72(12) . . . . ?
C20 C21 C26 C27 -5.99(18) . . . . ?
C21 C22 C23 C24 0.97(19) . . . . ?
C21 C26 C27 C28 123.86(12) . . . . ?
C21 C26 C27 C32 -57.90(16) . . . . ?
C22 N2 C18 C19 -0.9(2) . . . . ?
C22 C21 C26 C25 -4.04(17) . . . . ?
C22 C21 C26 C27 177.25(10) . . . . ?
C22 C23 C24 C25 -2.5(2) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C24 C25 C26 C21 2.62(19) . . . . ?
C24 C25 C26 C27 -178.65(11) . . . . ?
C25 C26 C27 C28 -54.85(16) . . . . ?
C25 C26 C27 C32 123.39(13) . . . . ?
C26 C21 C22 N2 -179.98(11) . . . . ?
C26 C21 C22 C23 2.29(17) . . . . ?
C26 C27 C28 C29 178.82(11) . . . . ?
C26 C27 C32 C31 -178.03(11) . . . . ?
C27 C28 C29 C30 -1.22(19) . . . . ?
C28 C27 C32 C31 0.23(17) . . . . ?
C28 C29 C30 C31 1.09(18) . . . . ?
C28 C29 C30 C33 -177.50(11) . . . . ?
C29 C30 C31 C32 -0.32(18) . . . . ?
C29 C30 C33 O2 170.48(13) . . . . ?
C29 C30 C33 C34 -9.56(19) . . . . ?
C30 C31 C32 C27 -0.34(18) . . . . ?
C31 C30 C33 O2 -8.11(19) . . . . ?
C31 C30 C33 C34 171.85(13) . . . . ?
C32 C27 C28 C29 0.54(18) . . . . ?
C33 C30 C31 C32 178.32(11) . . . . ?
N3 C35 C36 C37 1.8(2) . . . . ?
N3 C39 C40 C41 -177.91(13) . . . . ?
C35 N3 C39 C38 -1.7(2) . . . . ?
C35 N3 C39 C40 176.85(13) . . . . ?
C35 C36 C37 C38 -0.01(19) . . . . ?
C36 C37 C38 C39 -2.37(18) . . . . ?
C36 C37 C38 C43 -179.37(12) . . . . ?
C37 C38 C39 N3 3.35(18) . . . . ?
C37 C38 C39 C40 -175.21(12) . . . . ?
C37 C38 C43 C42 173.84(12) . . . . ?
C37 C38 C43 C44 -6.58(18) . . . . ?
C38 C39 C40 C41 0.7(2) . . . . ?
C38 C43 C44 C45 126.35(13) . . . . ?
C38 C43 C44 C49 -56.00(16) . . . . ?
C39 N3 C35 C36 -0.9(2) . . . . ?
C39 C38 C43 C42 -3.09(18) . . . . ?
C39 C38 C43 C44 176.49(10) . . . . ?
C39 C40 C41 C42 -2.2(2) . . . . ?
C40 C41 C42 C43 1.0(2) . . . . ?
C41 C42 C43 C38 1.7(2) . . . . ?
C41 C42 C43 C44 -177.93(12) . . . . ?
C42 C43 C44 C45 -54.07(17) . . . . ?
C42 C43 C44 C49 123.59(13) . . . . ?
C43 C38 C39 N3 -179.51(12) . . . . ?
C43 C38 C39 C40 1.93(18) . . . . ?
C43 C44 C45 C46 177.34(11) . . . . ?
C43 C44 C49 C48 -176.71(11) . . . . ?
C44 C45 C46 C47 -0.84(19) . . . . ?
C45 C44 C49 C48 0.96(18) . . . . ?
C45 C46 C47 C48 1.46(18) . . . . ?
C45 C46 C47 C50 -177.53(11) . . . . ?
C46 C47 C48 C49 -0.88(17) . . . . ?
C46 C47 C50 O3 166.99(13) . . . . ?
C46 C47 C50 C51 -13.40(18) . . . . ?
C47 C48 C49 C44 -0.33(18) . . . . ?
C48 C47 C50 O3 -11.98(18) . . . . ?
C48 C47 C50 C51 167.62(12) . . . . ?
C49 C44 C45 C46 -0.38(18) . . . . ?
C50 C47 C48 C49 178.14(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
