# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201808344
_database_code_depnum_ccdc_archive 'CCDC 1863489'
loop_
_audit_author_name
_audit_author_address
'Yabo Li'
;Zhengzhou University
China
;
_audit_update_record             
;
2018-08-23 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2018-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 O2'
_chemical_formula_sum            'C23 H16 O2'
_chemical_formula_weight         324.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2
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'
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                   8.2170(3)
_cell_length_b                   23.5453(7)
_cell_length_c                   8.6771(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.908(4)
_cell_angle_gamma                90
_cell_volume                     1666.59(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2545
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5940
_cell_measurement_theta_min      5.1660
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6277
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         3.755
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega  -59.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega   11.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   84.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega   10.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   49.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
 10 omega   66.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega    6.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega   78.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 14 omega  121.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 57

#__ type_ start__ end____ width___ exp.time_
 15 omega   65.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   65.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00  112.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 75

#__ type_ start__ end____ width___ exp.time_
 20 omega  104.00  165.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 61

#__ type_ start__ end____ width___ exp.time_
 21 omega   45.00  137.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0001817000
_diffrn_orient_matrix_UB_12      0.0651995000
_diffrn_orient_matrix_UB_13      -0.0150685000
_diffrn_orient_matrix_UB_21      0.1886872000
_diffrn_orient_matrix_UB_22      0.0001473000
_diffrn_orient_matrix_UB_23      0.0285104000
_diffrn_orient_matrix_UB_31      0.0073563000
_diffrn_orient_matrix_UB_32      -0.0055771000
_diffrn_orient_matrix_UB_33      -0.1759255000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2455
_reflns_number_total             2957
_reflns_odcompleteness_completeness 99.48
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.047
_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)+(0.0846P)²+0.1340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1463
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
C1 C 0.3569(2) 0.55124(7) 0.7420(2) 0.0530(4) Uani 1 1 d . . . . .
C2 C 0.23629(19) 0.59192(6) 0.78960(18) 0.0433(4) Uani 1 1 d . . . . .
C3 C 0.26451(18) 0.61778(7) 0.94350(18) 0.0449(4) Uani 1 1 d . . . . .
H3 H 0.1939 0.6474 0.9601 0.054 Uiso 1 1 calc R . . . .
C4 C 0.3750(2) 0.60563(7) 1.06325(19) 0.0482(4) Uani 1 1 d . . . . .
H4 H 0.4469 0.5759 1.0514 0.058 Uiso 1 1 calc R . . . .
C5 C 0.39279(18) 0.63536(7) 1.21264(18) 0.0454(4) Uani 1 1 d . . . . .
C6 C 0.5034(2) 0.61524(8) 1.3348(2) 0.0557(4) Uani 1 1 d . . . . .
H6 H 0.5666 0.5834 1.3197 0.067 Uiso 1 1 calc R . . . .
C7 C 0.5210(2) 0.64172(9) 1.4779(2) 0.0614(5) Uani 1 1 d . . . . .
H7 H 0.5954 0.6275 1.5577 0.074 Uiso 1 1 calc R . . . .
C8 C 0.4303(2) 0.68859(9) 1.5032(2) 0.0606(5) Uani 1 1 d . . . . .
H8 H 0.4428 0.7064 1.5996 0.073 Uiso 1 1 calc R . . . .
C9 C 0.3199(3) 0.70930(9) 1.3844(2) 0.0654(5) Uani 1 1 d . . . . .
H9 H 0.2575 0.7412 1.4009 0.078 Uiso 1 1 calc R . . . .
C10 C 0.3010(2) 0.68313(8) 1.2414(2) 0.0570(4) Uani 1 1 d . . . . .
H10 H 0.2257 0.6976 1.1627 0.068 Uiso 1 1 calc R . . . .
C11 C 0.10332(18) 0.60665(6) 0.68669(17) 0.0421(4) Uani 1 1 d . . . . .
C12 C -0.02142(18) 0.64739(7) 0.73180(17) 0.0441(4) Uani 1 1 d . . . . .
C13 C -0.1361(2) 0.63059(8) 0.8276(2) 0.0580(4) Uani 1 1 d . . . . .
H13 H -0.1371 0.5933 0.8629 0.070 Uiso 1 1 calc R . . . .
C14 C -0.2493(2) 0.66945(12) 0.8708(3) 0.0756(6) Uani 1 1 d . . . . .
H14 H -0.3271 0.6579 0.9337 0.091 Uiso 1 1 calc R . . . .
C15 C -0.2471(3) 0.72472(11) 0.8212(3) 0.0773(7) Uani 1 1 d . . . . .
H15 H -0.3217 0.7508 0.8523 0.093 Uiso 1 1 calc R . . . .
C16 C -0.1347(3) 0.74143(9) 0.7257(3) 0.0752(6) Uani 1 1 d . . . . .
H16 H -0.1331 0.7789 0.6918 0.090 Uiso 1 1 calc R . . . .
C17 C -0.0241(2) 0.70280(8) 0.6797(2) 0.0600(5) Uani 1 1 d . . . . .
H17 H 0.0499 0.7142 0.6127 0.072 Uiso 1 1 calc R . . . .
C18 C 0.0827(2) 0.58325(6) 0.53132(18) 0.0447(4) Uani 1 1 d . . . . .
C19 C 0.1979(2) 0.54458(7) 0.49100(19) 0.0485(4) Uani 1 1 d . . . . .
C20 C 0.1890(2) 0.52054(8) 0.3447(2) 0.0602(5) Uani 1 1 d . . . . .
H20 H 0.2681 0.4949 0.3207 0.072 Uiso 1 1 calc R . . . .
C21 C 0.0612(3) 0.53533(9) 0.2360(2) 0.0640(5) Uani 1 1 d . . . . .
H21 H 0.0536 0.5195 0.1372 0.077 Uiso 1 1 calc R . . . .
C22 C -0.0564(3) 0.57340(9) 0.2711(2) 0.0632(5) Uani 1 1 d . . . . .
H22 H -0.1427 0.5830 0.1962 0.076 Uiso 1 1 calc R . . . .
C23 C -0.0465(2) 0.59739(8) 0.4172(2) 0.0549(4) Uani 1 1 d . . . . .
H23 H -0.1261 0.6231 0.4400 0.066 Uiso 1 1 calc R . . . .
O1 O 0.32792(15) 0.52855(5) 0.59576(14) 0.0558(3) Uani 1 1 d . . . . .
O2 O 0.48032(19) 0.53590(7) 0.81928(17) 0.0812(5) 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
C1 C2 1.473(2) . ?
C1 O1 1.371(2) . ?
C1 O2 1.202(2) . ?
C2 C3 1.461(2) . ?
C2 C11 1.370(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.326(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.465(2) . ?
C5 C6 1.394(2) . ?
C5 C10 1.393(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.364(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.490(2) . ?
C11 C18 1.447(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.380(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(2) . ?
C18 C23 1.402(2) . ?
C19 C20 1.384(2) . ?
C19 O1 1.370(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.370(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(3) . ?
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
O1 C1 C2 117.71(14) . . ?
O2 C1 C2 126.17(16) . . ?
O2 C1 O1 116.11(15) . . ?
C3 C2 C1 119.29(14) . . ?
C11 C2 C1 119.53(14) . . ?
C11 C2 C3 121.12(14) . . ?
C2 C3 H3 114.9 . . ?
C4 C3 C2 130.16(15) . . ?
C4 C3 H3 114.9 . . ?
C3 C4 H4 117.4 . . ?
C3 C4 C5 125.19(15) . . ?
C5 C4 H4 117.4 . . ?
C6 C5 C4 119.81(15) . . ?
C10 C5 C4 123.08(14) . . ?
C10 C5 C6 117.10(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.22(17) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.66(16) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.26(16) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.55(18) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.20(16) . . ?
C9 C10 H10 119.4 . . ?
C2 C11 C12 120.77(13) . . ?
C2 C11 C18 120.37(14) . . ?
C18 C11 C12 118.85(13) . . ?
C13 C12 C11 120.81(15) . . ?
C17 C12 C11 120.44(15) . . ?
C17 C12 C13 118.75(16) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.96(19) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.81(18) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.93(19) . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C11 118.52(15) . . ?
C19 C18 C23 117.33(15) . . ?
C23 C18 C11 124.15(15) . . ?
C20 C19 C18 122.48(17) . . ?
O1 C19 C18 120.96(14) . . ?
O1 C19 C20 116.56(16) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.66(18) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.84(16) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.22(18) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.48(18) . . ?
C22 C23 H23 119.8 . . ?
C19 O1 C1 122.80(13) . . ?

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
C1 C2 C3 C4 -9.9(3) . . . . ?
C1 C2 C11 C12 179.57(14) . . . . ?
C1 C2 C11 C18 -1.1(2) . . . . ?
C2 C1 O1 C19 3.8(2) . . . . ?
C2 C3 C4 C5 179.18(15) . . . . ?
C2 C11 C12 C13 -76.0(2) . . . . ?
C2 C11 C12 C17 103.55(18) . . . . ?
C2 C11 C18 C19 1.7(2) . . . . ?
C2 C11 C18 C23 -177.83(15) . . . . ?
C3 C2 C11 C12 -3.2(2) . . . . ?
C3 C2 C11 C18 176.16(13) . . . . ?
C3 C4 C5 C6 173.90(16) . . . . ?
C3 C4 C5 C10 -4.8(3) . . . . ?
C4 C5 C6 C7 -178.87(15) . . . . ?
C4 C5 C10 C9 179.01(17) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C11 C2 C3 C4 172.83(16) . . . . ?
C11 C12 C13 C14 178.76(16) . . . . ?
C11 C12 C17 C16 -177.41(17) . . . . ?
C11 C18 C19 C20 -179.27(15) . . . . ?
C11 C18 C19 O1 0.4(2) . . . . ?
C11 C18 C23 C22 179.48(15) . . . . ?
C12 C11 C18 C19 -178.91(13) . . . . ?
C12 C11 C18 C23 1.5(2) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C12 C17 C16 2.1(3) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C12 -1.7(3) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C18 C11 C12 C13 104.68(17) . . . . ?
C18 C11 C12 C17 -75.81(19) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C18 C19 O1 C1 -3.2(2) . . . . ?
C19 C18 C23 C22 -0.1(2) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C19 O1 C1 176.42(15) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C18 -0.2(3) . . . . ?
C23 C18 C19 C20 0.3(2) . . . . ?
C23 C18 C19 O1 179.95(14) . . . . ?
O1 C1 C2 C3 -178.88(14) . . . . ?
O1 C1 C2 C11 -1.6(2) . . . . ?
O1 C19 C20 C21 -179.93(15) . . . . ?
O2 C1 C2 C3 0.7(3) . . . . ?
O2 C1 C2 C11 178.03(19) . . . . ?
O2 C1 O1 C19 -175.87(17) . . . . ?

_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_201803207
_database_code_depnum_ccdc_archive 'CCDC 1863518'
loop_
_audit_author_name
_audit_author_address
'Yabo Li'
;Zhengzhou University
China
;
_audit_update_record             
;
2018-08-23 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2018-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 O2'
_chemical_formula_sum            'C24 H18 O2'
_chemical_formula_weight         338.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2
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'
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                   8.1912(4)
_cell_length_b                   25.2962(16)
_cell_length_c                   8.6202(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.497(4)
_cell_angle_gamma                90
_cell_volume                     1780.67(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1668
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.7290
_cell_measurement_theta_min      5.4060
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6554
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.048
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         5.417
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega -108.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega   64.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega   11.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
  6 omega   19.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega   41.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  -31.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -90.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega  -21.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  119.00  145.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
 14 omega   45.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
 16 omega  131.00  172.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
 17 omega   45.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 18 omega   54.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 19 omega   61.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 20 omega   49.00  127.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1164744000
_diffrn_orient_matrix_UB_12      -0.0052329000
_diffrn_orient_matrix_UB_13      0.1312340000
_diffrn_orient_matrix_UB_21      0.1413104000
_diffrn_orient_matrix_UB_22      0.0148994000
_diffrn_orient_matrix_UB_23      0.1205318000
_diffrn_orient_matrix_UB_31      -0.0459103000
_diffrn_orient_matrix_UB_32      0.0588497000
_diffrn_orient_matrix_UB_33      -0.0189365000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2172
_reflns_number_total             3173
_reflns_odcompleteness_completeness 99.79
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.026
_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)+(0.0684P)²+0.1700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1558
_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:
 C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
C1 C 0.0710(3) 0.56161(9) 0.1667(3) 0.0690(6) Uani 1 1 d . . . . .
C2 C 0.1874(3) 0.60056(7) 0.1139(2) 0.0570(5) Uani 1 1 d . . . . .
C3 C 0.3184(2) 0.61560(7) 0.2121(2) 0.0535(5) Uani 1 1 d . . . . .
C4 C 0.3448(3) 0.59247(7) 0.3657(2) 0.0562(5) Uani 1 1 d . . . . .
C5 C 0.2405(3) 0.55237(8) 0.4073(3) 0.0610(5) Uani 1 1 d . . . . .
C6 C 0.2605(3) 0.52711(8) 0.5494(3) 0.0687(6) Uani 1 1 d . . . . .
H6 H 0.1889 0.5003 0.5732 0.082 Uiso 1 1 calc R . . . .
C7 C 0.3864(3) 0.54161(8) 0.6560(3) 0.0675(6) Uani 1 1 d . . . . .
C8 C 0.4904(3) 0.58220(9) 0.6174(3) 0.0724(6) Uani 1 1 d . . . . .
H8 H 0.5748 0.5927 0.6893 0.087 Uiso 1 1 calc R . . . .
C9 C 0.4711(3) 0.60718(9) 0.4754(3) 0.0663(6) Uani 1 1 d . . . . .
H9 H 0.5427 0.6341 0.4523 0.080 Uiso 1 1 calc R . . . .
C10 C 0.4118(4) 0.51424(10) 0.8107(3) 0.0853(8) Uani 1 1 d . . . . .
H10A H 0.3625 0.5347 0.8883 0.128 Uiso 1 1 calc GR . . . .
H10B H 0.5270 0.5107 0.8389 0.128 Uiso 1 1 calc GR . . . .
H10C H 0.3622 0.4799 0.8037 0.128 Uiso 1 1 calc GR . . . .
C11 C 0.1565(3) 0.62444(8) -0.0398(2) 0.0590(5) Uani 1 1 d . . . . .
H11 H 0.2224 0.6532 -0.0592 0.071 Uiso 1 1 calc R . . . .
C12 C 0.0485(3) 0.61125(9) -0.1557(3) 0.0663(6) Uani 1 1 d . . . . .
H12 H -0.0194 0.5826 -0.1402 0.080 Uiso 1 1 calc R . . . .
C13 C 0.0274(3) 0.63816(9) -0.3068(3) 0.0620(5) Uani 1 1 d . . . . .
C14 C 0.1059(3) 0.68499(10) -0.3388(3) 0.0767(7) Uani 1 1 d . . . . .
H14 H 0.1757 0.7006 -0.2616 0.092 Uiso 1 1 calc R . . . .
C15 C 0.0832(4) 0.70899(12) -0.4819(3) 0.0902(8) Uani 1 1 d . . . . .
H15 H 0.1370 0.7405 -0.5000 0.108 Uiso 1 1 calc R . . . .
C16 C -0.0184(3) 0.68674(12) -0.5985(3) 0.0840(8) Uani 1 1 d . . . . .
H16 H -0.0330 0.7028 -0.6956 0.101 Uiso 1 1 calc R . . . .
C17 C -0.0974(3) 0.64076(12) -0.5696(3) 0.0848(8) Uani 1 1 d . . . . .
H17 H -0.1666 0.6254 -0.6477 0.102 Uiso 1 1 calc R . . . .
C18 C -0.0761(3) 0.61669(11) -0.4259(3) 0.0781(7) Uani 1 1 d . . . . .
H18 H -0.1321 0.5855 -0.4084 0.094 Uiso 1 1 calc R . . . .
C19 C 0.4373(2) 0.65656(8) 0.1651(2) 0.0547(5) Uani 1 1 d . . . . .
C20 C 0.4216(3) 0.70812(9) 0.2112(3) 0.0780(7) Uani 1 1 d . . . . .
H20 H 0.3371 0.7173 0.2720 0.094 Uiso 1 1 calc R . . . .
C21 C 0.5294(4) 0.74658(11) 0.1689(4) 0.0921(8) Uani 1 1 d . . . . .
H21 H 0.5163 0.7814 0.2002 0.111 Uiso 1 1 calc R . . . .
C22 C 0.6537(3) 0.73353(12) 0.0819(3) 0.0905(9) Uani 1 1 d . . . . .
H22 H 0.7248 0.7596 0.0518 0.109 Uiso 1 1 calc R . . . .
C23 C 0.6752(3) 0.68238(13) 0.0383(4) 0.0942(9) Uani 1 1 d . . . . .
H23 H 0.7629 0.6734 -0.0188 0.113 Uiso 1 1 calc R . . . .
C24 C 0.5662(3) 0.64352(10) 0.0792(3) 0.0762(7) Uani 1 1 d . . . . .
H24 H 0.5805 0.6087 0.0484 0.091 Uiso 1 1 calc R . . . .
O1 O -0.0573(2) 0.54890(8) 0.1001(2) 0.0985(6) Uani 1 1 d . . . . .
O2 O 0.1107(2) 0.53661(6) 0.30669(19) 0.0753(5) 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
C1 C2 1.468(3) . ?
C1 O1 1.201(3) . ?
C1 O2 1.379(3) . ?
C2 C3 1.368(3) . ?
C2 C11 1.460(3) . ?
C3 C4 1.448(3) . ?
C3 C19 1.500(3) . ?
C4 C5 1.391(3) . ?
C4 C9 1.396(3) . ?
C5 C6 1.380(3) . ?
C5 O2 1.378(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(3) . ?
C7 C8 1.391(3) . ?
C7 C10 1.503(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.324(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.468(3) . ?
C13 C14 1.386(3) . ?
C13 C18 1.390(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.364(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 C24 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.352(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.363(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.392(3) . ?
C24 H24 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
O1 C1 C2 126.6(2) . . ?
O1 C1 O2 115.7(2) . . ?
O2 C1 C2 117.7(2) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 C11 121.25(18) . . ?
C11 C2 C1 119.22(19) . . ?
C2 C3 C4 120.48(18) . . ?
C2 C3 C19 121.31(18) . . ?
C4 C3 C19 118.21(17) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 C9 117.2(2) . . ?
C9 C4 C3 124.13(19) . . ?
C6 C5 C4 122.3(2) . . ?
O2 C5 C4 120.5(2) . . ?
O2 C5 C6 117.2(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 118.6(2) . . ?
C6 C7 C10 120.9(2) . . ?
C8 C7 C10 120.5(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 H9 119.7 . . ?
C8 C9 C4 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11 115.1 . . ?
C12 C11 C2 129.7(2) . . ?
C12 C11 H11 115.1 . . ?
C11 C12 H12 117.3 . . ?
C11 C12 C13 125.3(2) . . ?
C13 C12 H12 117.3 . . ?
C14 C13 C12 123.3(2) . . ?
C14 C13 C18 116.9(2) . . ?
C18 C13 C12 119.8(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C3 120.04(19) . . ?
C20 C19 C24 118.5(2) . . ?
C24 C19 C3 121.44(19) . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 120.1(2) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C5 O2 C1 122.42(17) . . ?

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
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 C19 -177.95(18) . . . . ?
C1 C2 C11 C12 -11.3(3) . . . . ?
C2 C1 O2 C5 9.9(3) . . . . ?
C2 C3 C4 C5 4.0(3) . . . . ?
C2 C3 C4 C9 -177.1(2) . . . . ?
C2 C3 C19 C20 97.5(3) . . . . ?
C2 C3 C19 C24 -84.3(3) . . . . ?
C2 C11 C12 C13 180.0(2) . . . . ?
C3 C2 C11 C12 171.8(2) . . . . ?
C3 C4 C5 C6 177.88(19) . . . . ?
C3 C4 C5 O2 -2.7(3) . . . . ?
C3 C4 C9 C8 -178.2(2) . . . . ?
C3 C19 C20 C21 -179.8(2) . . . . ?
C3 C19 C24 C23 -179.5(2) . . . . ?
C4 C3 C19 C20 -81.9(3) . . . . ?
C4 C3 C19 C24 96.3(2) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C4 C5 O2 C1 -4.5(3) . . . . ?
C5 C4 C9 C8 0.6(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C10 -179.3(2) . . . . ?
C6 C5 O2 C1 174.9(2) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C9 C4 C5 C6 -1.0(3) . . . . ?
C9 C4 C5 O2 178.38(19) . . . . ?
C10 C7 C8 C9 178.9(2) . . . . ?
C11 C2 C3 C4 178.39(17) . . . . ?
C11 C2 C3 C19 -1.0(3) . . . . ?
C11 C12 C13 C14 -8.1(4) . . . . ?
C11 C12 C13 C18 172.1(2) . . . . ?
C12 C13 C14 C15 179.9(2) . . . . ?
C12 C13 C18 C17 -179.4(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C13 C18 C17 0.8(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C18 C13 C14 C15 -0.3(4) . . . . ?
C19 C3 C4 C5 -176.52(18) . . . . ?
C19 C3 C4 C9 2.3(3) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C20 C19 C24 C23 -1.3(4) . . . . ?
C20 C21 C22 C23 -1.3(5) . . . . ?
C21 C22 C23 C24 2.0(5) . . . . ?
C22 C23 C24 C19 -0.7(4) . . . . ?
C24 C19 C20 C21 1.9(4) . . . . ?
O1 C1 C2 C3 171.8(2) . . . . ?
O1 C1 C2 C11 -5.2(4) . . . . ?
O1 C1 O2 C5 -170.1(2) . . . . ?
O2 C1 C2 C3 -8.3(3) . . . . ?
O2 C1 C2 C11 174.73(18) . . . . ?
O2 C5 C6 C7 -179.02(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_201809374a
_database_code_depnum_ccdc_archive 'CCDC 1871889'
loop_
_audit_author_name
_audit_author_address
'Yabo Li'
;Zhengzhou University
China
;
_audit_update_record             
;
2018-10-08 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2018-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 O3'
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2Cl1
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'
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                   12.2348(12)
_cell_length_b                   6.8428(7)
_cell_length_c                   23.447(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.176(9)
_cell_angle_gamma                90
_cell_volume                     1932.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1079
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3270
_cell_measurement_theta_min      4.8080
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7182
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.670
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega   65.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega   82.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   59.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   18.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega   -1.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  8 omega   22.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
  9 omega   57.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   58.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega  122.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 14 omega  107.00  148.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 15 omega   55.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -24.0000  117.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   50.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 61

#__ type_ start__ end____ width___ exp.time_
 19 omega   79.00  148.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -180.0000 69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1151784000
_diffrn_orient_matrix_UB_12      0.0653381000
_diffrn_orient_matrix_UB_13      -0.0107024000
_diffrn_orient_matrix_UB_21      -0.0465912000
_diffrn_orient_matrix_UB_22      0.0228407000
_diffrn_orient_matrix_UB_23      -0.0651038000
_diffrn_orient_matrix_UB_31      -0.0302001000
_diffrn_orient_matrix_UB_32      0.2142691000
_diffrn_orient_matrix_UB_33      0.0101708000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1880
_reflns_number_total             3445
_reflns_odcompleteness_completeness 99.87
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      1.021
_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)+(0.1497P)²+0.0558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2180
_refine_ls_wR_factor_ref         0.2779
_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:
 C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C25(H25A,H25B,H25C)
;
_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
C1 C -0.1040(3) 0.7504(4) 0.50123(13) 0.0464(7) Uani 1 1 d . . . . .
C2 C -0.0231(2) 0.7424(4) 0.46107(12) 0.0431(7) Uani 1 1 d . . . . .
C3 C -0.0607(2) 0.7327(4) 0.40275(12) 0.0439(7) Uani 1 1 d . . . . .
C4 C -0.1788(3) 0.7342(4) 0.37986(13) 0.0459(7) Uani 1 1 d . . . . .
C5 C -0.2531(3) 0.7436(4) 0.41842(13) 0.0472(7) Uani 1 1 d . . . . .
C6 C -0.3668(3) 0.7472(4) 0.40053(15) 0.0547(8) Uani 1 1 d . . . . .
H6 H -0.4134 0.7514 0.4278 0.066 Uiso 1 1 calc R . . . .
C7 C -0.4112(3) 0.7446(5) 0.34258(15) 0.0571(8) Uani 1 1 d . . . . .
C8 C -0.3386(3) 0.7365(5) 0.30259(14) 0.0601(9) Uani 1 1 d . . . . .
H8 H -0.3675 0.7345 0.2631 0.072 Uiso 1 1 calc R . . . .
C9 C -0.2259(3) 0.7315(4) 0.32069(13) 0.0555(8) Uani 1 1 d . . . . .
H9 H -0.1796 0.7262 0.2933 0.067 Uiso 1 1 calc R . . . .
C10 C -0.5353(3) 0.7488(6) 0.32253(19) 0.0771(11) Uani 1 1 d . . . . .
H10A H -0.5678 0.6345 0.3364 0.116 Uiso 1 1 calc GR . . . .
H10B H -0.5515 0.7509 0.2810 0.116 Uiso 1 1 calc GR . . . .
H10C H -0.5655 0.8636 0.3374 0.116 Uiso 1 1 calc GR . . . .
C11 C 0.0169(2) 0.7197(5) 0.36048(12) 0.0502(8) Uani 1 1 d . . . . .
C12 C 0.0218(3) 0.5449(6) 0.32979(15) 0.0758(11) Uani 1 1 d . . . . .
H12 H -0.0222 0.4392 0.3363 0.091 Uiso 1 1 calc R . . . .
C13 C 0.0916(4) 0.5299(9) 0.29002(18) 0.0984(16) Uani 1 1 d . . . . .
H13 H 0.0934 0.4151 0.2690 0.118 Uiso 1 1 calc R . . . .
C14 C 0.1592(4) 0.6855(10) 0.28125(18) 0.1044(19) Uani 1 1 d . . . . .
H14 H 0.2072 0.6746 0.2548 0.125 Uiso 1 1 calc R . . . .
C15 C 0.1553(4) 0.8523(9) 0.31115(19) 0.0986(16) Uani 1 1 d . . . . .
H15 H 0.2007 0.9566 0.3051 0.118 Uiso 1 1 calc R . . . .
C16 C 0.0838(3) 0.8707(7) 0.35106(15) 0.0759(11) Uani 1 1 d . . . . .
H16 H 0.0819 0.9871 0.3714 0.091 Uiso 1 1 calc R . . . .
C17 C 0.0942(3) 0.7388(4) 0.48566(13) 0.0480(7) Uani 1 1 d . . . . .
H17 H 0.1411 0.7196 0.4589 0.058 Uiso 1 1 calc R . . . .
C18 C 0.1456(3) 0.7585(4) 0.53994(13) 0.0486(7) Uani 1 1 d . . . . .
H18 H 0.1005 0.7761 0.5676 0.058 Uiso 1 1 calc R . . . .
C19 C 0.2649(3) 0.7556(4) 0.56126(13) 0.0488(7) Uani 1 1 d . . . . .
C20 C 0.3447(3) 0.7523(5) 0.52545(14) 0.0620(9) Uani 1 1 d . . . . .
H20 H 0.3216 0.7528 0.4855 0.074 Uiso 1 1 calc R . . . .
C21 C 0.4579(3) 0.7483(5) 0.54786(15) 0.0682(10) Uani 1 1 d . . . . .
H21 H 0.5092 0.7459 0.5230 0.082 Uiso 1 1 calc R . . . .
C22 C 0.4938(3) 0.7478(5) 0.60711(14) 0.0576(8) Uani 1 1 d . . . . .
C23 C 0.4153(3) 0.7541(5) 0.64343(13) 0.0580(9) Uani 1 1 d . . . . .
H23 H 0.4386 0.7548 0.6834 0.070 Uiso 1 1 calc R . . . .
C24 C 0.3035(3) 0.7591(4) 0.62085(13) 0.0537(8) Uani 1 1 d . . . . .
H24 H 0.2526 0.7650 0.6459 0.064 Uiso 1 1 calc R . . . .
C25 C 0.6844(3) 0.7304(7) 0.5976(2) 0.0986(16) Uani 1 1 d . . . . .
H25A H 0.6772 0.8404 0.5718 0.148 Uiso 1 1 calc GR . . . .
H25B H 0.6742 0.6118 0.5754 0.148 Uiso 1 1 calc GR . . . .
H25C H 0.7569 0.7309 0.6212 0.148 Uiso 1 1 calc GR . . . .
O1 O -0.0829(2) 0.7553(3) 0.55310(9) 0.0603(7) Uani 1 1 d . . . . .
O2 O -0.21523(18) 0.7491(3) 0.47710(9) 0.0505(6) Uani 1 1 d . . . . .
O3 O 0.6021(2) 0.7427(4) 0.63385(11) 0.0793(9) 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
C1 C2 1.483(4) . ?
C1 O1 1.198(4) . ?
C1 O2 1.379(4) . ?
C2 C3 1.365(4) . ?
C2 C17 1.450(4) . ?
C3 C4 1.450(4) . ?
C3 C11 1.492(4) . ?
C4 C5 1.392(4) . ?
C4 C9 1.405(4) . ?
C5 C6 1.380(4) . ?
C5 O2 1.372(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(5) . ?
C7 C8 1.402(5) . ?
C7 C10 1.508(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.370(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.403(5) . ?
C11 C16 1.360(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.345(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.395(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.323(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.457(4) . ?
C19 C20 1.396(5) . ?
C19 C24 1.394(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(5) . ?
C22 C23 1.392(5) . ?
C22 O3 1.362(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.377(5) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 O3 1.430(5) . ?

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
O1 C1 C2 126.7(3) . . ?
O1 C1 O2 115.9(3) . . ?
O2 C1 C2 117.4(3) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 C17 122.2(3) . . ?
C17 C2 C1 118.2(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 C11 121.8(3) . . ?
C4 C3 C11 117.7(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C9 116.2(3) . . ?
C9 C4 C3 125.0(3) . . ?
C6 C5 C4 122.8(3) . . ?
O2 C5 C4 120.6(3) . . ?
O2 C5 C6 116.6(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 118.5(3) . . ?
C6 C7 C10 120.6(3) . . ?
C8 C7 C10 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.3(3) . . ?
C8 C9 H9 119.3 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C3 118.8(3) . . ?
C16 C11 C3 122.3(3) . . ?
C16 C11 C12 118.9(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(4) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.7(5) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 120.5(4) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C2 C17 H17 114.7 . . ?
C18 C17 C2 130.5(3) . . ?
C18 C17 H17 114.7 . . ?
C17 C18 H18 116.4 . . ?
C17 C18 C19 127.2(3) . . ?
C19 C18 H18 116.4 . . ?
C20 C19 C18 124.0(3) . . ?
C24 C19 C18 119.0(3) . . ?
C24 C19 C20 117.0(3) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 C19 121.9(3) . . ?
C21 C20 H20 119.1 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 118.9(3) . . ?
O3 C22 C21 125.0(3) . . ?
O3 C22 C23 116.1(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.6 . . ?
C19 C24 H24 119.2 . . ?
C23 C24 C19 121.5(3) . . ?
C23 C24 H24 119.2 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
C5 O2 C1 123.1(2) . . ?
C22 O3 C25 117.2(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
C1 C2 C3 C4 1.3(4) . . . . ?
C1 C2 C3 C11 -178.6(3) . . . . ?
C1 C2 C17 C18 -6.6(5) . . . . ?
C2 C1 O2 C5 -0.9(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C9 177.7(3) . . . . ?
C2 C3 C11 C12 110.8(3) . . . . ?
C2 C3 C11 C16 -68.6(4) . . . . ?
C2 C17 C18 C19 -179.2(3) . . . . ?
C3 C2 C17 C18 175.4(3) . . . . ?
C3 C4 C5 C6 179.5(3) . . . . ?
C3 C4 C5 O2 -0.8(4) . . . . ?
C3 C4 C9 C8 -178.9(3) . . . . ?
C3 C11 C12 C13 179.2(3) . . . . ?
C3 C11 C16 C15 180.0(4) . . . . ?
C4 C3 C11 C12 -69.1(4) . . . . ?
C4 C3 C11 C16 111.6(3) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C4 C5 O2 C1 1.6(4) . . . . ?
C5 C4 C9 C8 -0.5(4) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C5 C6 C7 C10 -179.9(3) . . . . ?
C6 C5 O2 C1 -178.7(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C4 0.0(5) . . . . ?
C9 C4 C5 C6 1.0(4) . . . . ?
C9 C4 C5 O2 -179.3(3) . . . . ?
C10 C7 C8 C9 -179.6(3) . . . . ?
C11 C3 C4 C5 179.2(3) . . . . ?
C11 C3 C4 C9 -2.4(4) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C12 C11 C16 C15 0.6(5) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C14 C15 C16 C11 0.1(7) . . . . ?
C16 C11 C12 C13 -1.4(5) . . . . ?
C17 C2 C3 C4 179.2(2) . . . . ?
C17 C2 C3 C11 -0.6(4) . . . . ?
C17 C18 C19 C20 7.4(5) . . . . ?
C17 C18 C19 C24 -173.6(3) . . . . ?
C18 C19 C20 C21 -179.6(3) . . . . ?
C18 C19 C24 C23 179.1(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C19 C24 C23 -1.8(5) . . . . ?
C20 C21 C22 C23 -0.9(5) . . . . ?
C20 C21 C22 O3 179.5(3) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C21 C22 O3 C25 -2.2(5) . . . . ?
C22 C23 C24 C19 0.9(5) . . . . ?
C23 C22 O3 C25 178.2(3) . . . . ?
C24 C19 C20 C21 1.4(5) . . . . ?
O1 C1 C2 C3 178.4(3) . . . . ?
O1 C1 C2 C17 0.4(4) . . . . ?
O1 C1 O2 C5 -180.0(2) . . . . ?
O2 C1 C2 C3 -0.5(4) . . . . ?
O2 C1 C2 C17 -178.5(2) . . . . ?
O2 C5 C6 C7 179.2(3) . . . . ?
O3 C22 C23 C24 -179.9(3) . . . . ?

_olex2_date_sample_data_collection 1537181979.33
_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_201809371
_database_code_depnum_ccdc_archive 'CCDC 1871888'
loop_
_audit_author_name
_audit_author_address
'Yabo Li'
;Zhengzhou University
China
;
_audit_update_record             
;
2018-10-08 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2018-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H17 Cl O2'
_chemical_formula_sum            'C24 H17 Cl O2'
_chemical_formula_weight         372.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N4Cl1
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   12.6928(4)
_cell_length_b                   7.0340(3)
_cell_length_c                   21.7643(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1943.16(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1460
_cell_measurement_theta_min      4.0160
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    1.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4210
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.032
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   33.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   60.0000 164

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00  -22.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   36.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00   82.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega   60.00   88.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega   76.00  106.00   0.5000    3.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00  104.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 130

#__ type_ start__ end____ width___ exp.time_
  8 omega   54.00  107.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
  9 omega   54.00   80.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   62.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  169.00   0.5000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -120.0000 262
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1064366000
_diffrn_orient_matrix_UB_12      -0.0495235000
_diffrn_orient_matrix_UB_13      -0.0300128000
_diffrn_orient_matrix_UB_21      -0.0386947000
_diffrn_orient_matrix_UB_22      0.0846571000
_diffrn_orient_matrix_UB_23      -0.0612662000
_diffrn_orient_matrix_UB_31      0.0436408000
_diffrn_orient_matrix_UB_32      0.1958040000
_diffrn_orient_matrix_UB_33      0.0189016000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1302
_reflns_number_total             1890
_reflns_odcompleteness_completeness 99.66
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.295
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1890
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0728
_refine_ls_restrained_S_all      1.214
_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)+(0.1336P)²+0.3204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2326
_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. Restrained distances
 C6-C5
 1.4 with sigma of 0.02
 C6-C1
 1.4 with sigma of 0.02
 C5-C4
 1.4 with sigma of 0.02
 C4-C3
 1.5 with sigma of 0.02
 C2-C1
 1.4 with sigma of 0.02
 C3-C2
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: H18A(0.5) H18B(0.5) H18C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C16(H16),
 C17(H17), C20(H20), C21(H21)
5.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
C1 C 0.1668(6) 0.2500 0.2650(2) 0.117(2) Uani 1 2 d DS TU P . .
H1 H 0.0946 0.2500 0.2576 0.140 Uiso 1 2 calc RS T P . .
C2 C 0.2341(7) 0.2500 0.2149(3) 0.125(2) Uani 1 2 d DS TU P . .
H2 H 0.2073 0.2500 0.1752 0.150 Uiso 1 2 calc RS T P . .
C3 C 0.3399(8) 0.2500 0.2246(3) 0.151(3) Uani 1 2 d DS TU P . .
H3 H 0.3872 0.2500 0.1920 0.182 Uiso 1 2 calc RS T P . .
C4 C 0.3744(9) 0.2500 0.2844(4) 0.204(4) Uani 1 2 d DS TU P . .
H4 H 0.4465 0.2500 0.2921 0.245 Uiso 1 2 calc RS T P . .
C5 C 0.3059(6) 0.2500 0.3333(3) 0.157(3) Uani 1 2 d DS TU P . .
H5 H 0.3322 0.2500 0.3732 0.188 Uiso 1 2 calc RS T P . .
C6 C 0.1998(4) 0.2500 0.32403(19) 0.0845(13) Uani 1 2 d DS TU P . .
C7 C 0.1241(4) 0.2500 0.37431(19) 0.0764(11) Uani 1 2 d S T P . .
H7 H 0.0533 0.2500 0.3635 0.092 Uiso 1 2 calc RS T P . .
C8 C 0.1454(3) 0.2500 0.43280(16) 0.0665(10) Uani 1 2 d S T P . .
H8 H 0.2170 0.2500 0.4420 0.080 Uiso 1 2 calc RS T P . .
C9 C -0.0389(3) 0.2500 0.47813(16) 0.0592(9) Uani 1 2 d S T P . .
C10 C 0.0767(3) 0.2500 0.48629(14) 0.0534(8) Uani 1 2 d S T P . .
C11 C 0.1167(3) 0.2500 0.54469(16) 0.0586(9) Uani 1 2 d S T P . .
C12 C 0.0481(3) 0.2500 0.59719(16) 0.0606(9) Uani 1 2 d S T P . .
C13 C -0.0597(3) 0.2500 0.58784(16) 0.0570(8) Uani 1 2 d S T P . .
C14 C -0.1310(3) 0.2500 0.6365(2) 0.0723(11) Uani 1 2 d S T P . .
H14 H -0.2029 0.2500 0.6285 0.087 Uiso 1 2 calc RS T P . .
C15 C -0.0964(4) 0.2500 0.6958(2) 0.0813(12) Uani 1 2 d S T P . .
C16 C 0.0112(4) 0.2500 0.7060(2) 0.0979(16) Uani 1 2 d S T P . .
H16 H 0.0361 0.2500 0.7462 0.117 Uiso 1 2 calc RS T P . .
C17 C 0.0821(4) 0.2500 0.65843(19) 0.0868(14) Uani 1 2 d S T P . .
H17 H 0.1539 0.2500 0.6670 0.104 Uiso 1 2 calc RS T P . .
C18 C -0.1726(5) 0.2500 0.7482(3) 0.116(2) Uani 1 2 d S T P . .
H18A H -0.2344 0.1796 0.7370 0.175 Uiso 0.5 1 calc GR . . A -1
H18B H -0.1919 0.3785 0.7580 0.175 Uiso 0.5 1 calc GR . . A -1
H18C H -0.1403 0.1919 0.7834 0.175 Uiso 0.5 1 calc GR . . A -1
C19 C 0.2334(3) 0.2500 0.55504(16) 0.0668(10) Uani 1 2 d S T P . .
C20 C 0.2879(3) 0.4141(7) 0.5597(2) 0.1045(13) Uani 1 1 d . . . . .
H20 H 0.2518 0.5289 0.5567 0.125 Uiso 1 1 calc R . . . .
C21 C 0.3965(3) 0.4167(8) 0.5686(2) 0.1210(16) Uani 1 1 d . . . . .
H21 H 0.4329 0.5311 0.5713 0.145 Uiso 1 1 calc R . . . .
C22 C 0.4473(4) 0.2500 0.5734(3) 0.1055(19) Uani 1 2 d S T P . .
Cl1 Cl 0.58328(11) 0.2500 0.58469(14) 0.1863(13) Uani 1 2 d S T P . .
O1 O -0.0854(2) 0.2500 0.43058(12) 0.0785(9) Uani 1 2 d S T P . .
O2 O -0.10079(18) 0.2500 0.52985(12) 0.0659(7) Uani 1 2 d S 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
C1 H1 0.9300 . ?
C1 C2 1.385(8) . ?
C1 C6 1.351(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.362(9) . ?
C6 C7 1.456(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.301(6) . ?
C8 H8 0.9300 . ?
C8 C10 1.455(5) . ?
C9 C10 1.478(5) . ?
C9 O1 1.191(4) . ?
C9 O2 1.373(4) . ?
C10 C11 1.369(5) . ?
C11 C12 1.437(5) . ?
C11 C19 1.498(5) . ?
C12 C13 1.383(5) . ?
C12 C17 1.401(6) . ?
C13 C14 1.393(5) . ?
C13 O2 1.365(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.362(7) . ?
C15 C16 1.384(7) . ?
C15 C18 1.496(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(7) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.350(5) 8_565 ?
C19 C20 1.350(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.342(6) . ?
C22 C21 1.342(6) 8_565 ?
C22 Cl1 1.743(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.1 . . ?
C6 C1 H1 118.1 . . ?
C6 C1 C2 123.9(7) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.5(7) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.2(10) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(8) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 116.6(5) . . ?
C1 C6 C7 120.7(5) . . ?
C5 C6 C7 122.7(5) . . ?
C6 C7 H7 116.6 . . ?
C8 C7 C6 126.8(5) . . ?
C8 C7 H7 116.6 . . ?
C7 C8 H8 114.4 . . ?
C7 C8 C10 131.2(4) . . ?
C10 C8 H8 114.4 . . ?
O1 C9 C10 126.6(3) . . ?
O1 C9 O2 115.4(3) . . ?
O2 C9 C10 118.0(3) . . ?
C8 C10 C9 119.9(3) . . ?
C11 C10 C8 121.4(3) . . ?
C11 C10 C9 118.7(3) . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 C19 120.4(3) . . ?
C12 C11 C19 118.7(3) . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 C17 116.4(3) . . ?
C17 C12 C11 124.7(4) . . ?
C12 C13 C14 122.0(4) . . ?
O2 C13 C12 120.9(3) . . ?
O2 C13 C14 117.1(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 118.0(4) . . ?
C14 C15 C18 120.9(5) . . ?
C16 C15 C18 121.0(5) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.8(4) . . ?
C17 C16 H16 119.1 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.0(4) . . ?
C16 C17 H17 119.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C11 121.2(2) . . ?
C20 C19 C11 121.2(2) 8_565 . ?
C20 C19 C20 117.6(4) 8_565 . ?
C19 C20 H20 119.0 . . ?
C19 C20 C21 121.9(4) . . ?
C21 C20 H20 119.0 . . ?
C20 C21 H21 120.8 . . ?
C22 C21 C20 118.4(5) . . ?
C22 C21 H21 120.8 . . ?
C21 C22 C21 121.8(5) . 8_565 ?
C21 C22 Cl1 119.1(2) 8_565 . ?
C21 C22 Cl1 119.1(2) . . ?
C13 O2 C9 122.7(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
C1 C2 C3 C4 0.000(1) . . . . ?
C1 C6 C7 C8 180.000(1) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
C2 C1 C6 C7 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C4 C5 C6 C1 0.000(1) . . . . ?
C4 C5 C6 C7 180.000(1) . . . . ?
C5 C6 C7 C8 0.000(1) . . . . ?
C6 C1 C2 C3 0.000(1) . . . . ?
C6 C7 C8 C10 180.000(1) . . . . ?
C7 C8 C10 C9 0.000(1) . . . . ?
C7 C8 C10 C11 180.000(1) . . . . ?
C8 C10 C11 C12 180.000(1) . . . . ?
C8 C10 C11 C19 0.000(1) . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C9 C10 C11 C19 180.000(1) . . . . ?
C10 C9 O2 C13 0.000(1) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
C10 C11 C12 C17 180.000(1) . . . . ?
C10 C11 C19 C20 89.8(4) . . . . ?
C10 C11 C19 C20 -89.8(4) . . . 8_565 ?
C11 C12 C13 C14 180.000(1) . . . . ?
C11 C12 C13 O2 0.000(1) . . . . ?
C11 C12 C17 C16 180.000(1) . . . . ?
C11 C19 C20 C21 -179.3(4) . . . . ?
C12 C11 C19 C20 -90.2(4) . . . . ?
C12 C11 C19 C20 90.2(4) . . . 8_565 ?
C12 C13 C14 C15 0.000(2) . . . . ?
C12 C13 O2 C9 0.000(1) . . . . ?
C13 C12 C17 C16 0.000(2) . . . . ?
C13 C14 C15 C16 0.000(2) . . . . ?
C13 C14 C15 C18 180.000(2) . . . . ?
C14 C13 O2 C9 180.000(1) . . . . ?
C14 C15 C16 C17 0.000(2) . . . . ?
C15 C16 C17 C12 0.000(2) . . . . ?
C17 C12 C13 C14 0.000(1) . . . . ?
C17 C12 C13 O2 180.000(1) . . . . ?
C18 C15 C16 C17 180.000(2) . . . . ?
C19 C11 C12 C13 180.000(1) . . . . ?
C19 C11 C12 C17 0.000(1) . . . . ?
C19 C20 C21 C22 -0.7(8) . . . . ?
C20 C19 C20 C21 0.2(8) 8_565 . . . ?
C20 C21 C22 C21 1.2(10) . . . 8_565 ?
C20 C21 C22 Cl1 -180.0(4) . . . . ?
O1 C9 C10 C8 0.000(1) . . . . ?
O1 C9 C10 C11 180.000(1) . . . . ?
O1 C9 O2 C13 180.000(1) . . . . ?
O2 C9 C10 C8 180.000(1) . . . . ?
O2 C9 C10 C11 0.000(1) . . . . ?
O2 C13 C14 C15 180.000(1) . . . . ?

_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_201808345
_database_code_depnum_ccdc_archive 'CCDC 1863491'
loop_
_audit_author_name
_audit_author_address
'Yabo Li'
;Zhengzhou University
China
;
_audit_update_record             
;
2018-08-23 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2018-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H18 O2'
_chemical_formula_sum            'C27 H18 O2'
_chemical_formula_weight         374.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2
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'
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                   9.4150(6)
_cell_length_b                   10.3881(7)
_cell_length_c                   11.1903(7)
_cell_angle_alpha                78.293(6)
_cell_angle_beta                 85.937(5)
_cell_angle_gamma                65.446(6)
_cell_volume                     974.65(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1239
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.1670
_cell_measurement_theta_min      4.7570
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6939
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.035
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   37.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   90.0000 172

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -15.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -60.0000 174

#__ type_ start__ end____ width___ exp.time_
  3 omega   14.00  107.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 186

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   77.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 162

#__ type_ start__ end____ width___ exp.time_
  5 omega   -4.00   77.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 162

#__ type_ start__ end____ width___ exp.time_
  6 omega   18.00  105.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 174

#__ type_ start__ end____ width___ exp.time_
  7 omega    8.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 196

#__ type_ start__ end____ width___ exp.time_
  8 omega  -33.00   65.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 196

#__ type_ start__ end____ width___ exp.time_
  9 omega   20.00   46.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega   57.00   93.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 72

#__ type_ start__ end____ width___ exp.time_
 11 omega   10.00   36.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   20.00   66.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
 13 omega   60.00  109.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   98.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 15 omega  144.00  170.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega   37.00   85.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   68.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
 18 omega   69.00  128.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 118

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00  115.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 156

#__ type_ start__ end____ width___ exp.time_
 20 omega   45.00   83.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 76

#__ type_ start__ end____ width___ exp.time_
 21 omega  102.00  128.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 22 omega   78.00  104.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
 23 omega   82.00  115.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
 24 omega  125.00  153.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 25 omega   67.00  117.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 26 omega   59.00   85.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 27 omega  141.00  178.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
 28 omega   42.00   87.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 29 omega   83.00  135.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
 30 omega   68.00  104.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
 31 omega   43.00  122.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 158

#__ type_ start__ end____ width___ exp.time_
 32 omega   37.00   66.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 33 omega   88.00  130.00   0.5000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1543770000
_diffrn_orient_matrix_UB_12      0.1361133000
_diffrn_orient_matrix_UB_13      -0.0216485000
_diffrn_orient_matrix_UB_21      -0.0889986000
_diffrn_orient_matrix_UB_22      -0.0880724000
_diffrn_orient_matrix_UB_23      0.0672038000
_diffrn_orient_matrix_UB_31      0.0248501000
_diffrn_orient_matrix_UB_32      0.0361815000
_diffrn_orient_matrix_UB_33      0.1215986000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2039
_reflns_number_total             3476
_reflns_odcompleteness_completeness 99.83
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.018
_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)+(0.0754P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1704
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26),
  C27(H27)
;
_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
C1 C 0.0402(3) 1.0537(3) 0.2186(2) 0.0627(6) Uani 1 1 d . . . . .
C2 C 0.0425(3) 0.9168(2) 0.2003(2) 0.0557(6) Uani 1 1 d . . . . .
C3 C 0.1467(3) 0.8448(3) 0.1077(2) 0.0629(6) Uani 1 1 d . . . . .
H3 H 0.1334 0.7664 0.0908 0.076 Uiso 1 1 calc R . . . .
C4 C 0.2565(3) 0.8752(3) 0.0452(2) 0.0659(7) Uani 1 1 d . . . . .
H4 H 0.2683 0.9560 0.0575 0.079 Uiso 1 1 calc R . . . .
C5 C 0.3613(3) 0.7940(3) -0.0418(2) 0.0639(6) Uani 1 1 d . . . . .
C6 C 0.4908(4) 0.8204(3) -0.0830(3) 0.0841(9) Uani 1 1 d . . . . .
H6 H 0.5071 0.8928 -0.0570 0.101 Uiso 1 1 calc R . . . .
C7 C 0.5960(4) 0.7427(4) -0.1612(3) 0.0957(10) Uani 1 1 d . . . . .
H7 H 0.6837 0.7605 -0.1857 0.115 Uiso 1 1 calc R . . . .
C8 C 0.5699(4) 0.6397(4) -0.2020(3) 0.1068(12) Uani 1 1 d . . . . .
H8 H 0.6401 0.5865 -0.2548 0.128 Uiso 1 1 calc R . . . .
C9 C 0.4409(5) 0.6140(4) -0.1659(3) 0.1103(12) Uani 1 1 d . . . . .
H9 H 0.4227 0.5453 -0.1963 0.132 Uiso 1 1 calc R . . . .
C10 C 0.3377(4) 0.6884(4) -0.0852(3) 0.0858(9) Uani 1 1 d . . . . .
H10 H 0.2519 0.6679 -0.0598 0.103 Uiso 1 1 calc R . . . .
C11 C -0.0482(3) 0.8577(2) 0.2703(2) 0.0539(6) Uani 1 1 d . . . . .
C12 C -0.0554(3) 0.7228(2) 0.2481(2) 0.0559(6) Uani 1 1 d . . . . .
C13 C -0.1333(4) 0.7258(3) 0.1478(3) 0.0881(10) Uani 1 1 d . . . . .
H13 H -0.1827 0.8126 0.0938 0.106 Uiso 1 1 calc R . . . .
C14 C -0.1398(5) 0.6027(4) 0.1255(3) 0.1054(12) Uani 1 1 d . . . . .
H14 H -0.1943 0.6073 0.0575 0.126 Uiso 1 1 calc R . . . .
C15 C -0.0665(4) 0.4741(3) 0.2029(3) 0.0870(9) Uani 1 1 d . . . . .
H15 H -0.0689 0.3905 0.1872 0.104 Uiso 1 1 calc R . . . .
C16 C 0.0104(3) 0.4694(3) 0.3037(3) 0.0768(8) Uani 1 1 d . . . . .
H16 H 0.0594 0.3823 0.3573 0.092 Uiso 1 1 calc R . . . .
C17 C 0.0162(3) 0.5927(3) 0.3268(2) 0.0662(7) Uani 1 1 d . . . . .
H17 H 0.0688 0.5880 0.3960 0.079 Uiso 1 1 calc R . . . .
C18 C -0.1436(3) 1.0542(2) 0.3817(2) 0.0574(6) Uani 1 1 d . . . . .
C19 C -0.1414(3) 0.9247(2) 0.3667(2) 0.0567(6) Uani 1 1 d . . . . .
C20 C -0.2318(3) 0.8654(3) 0.4471(2) 0.0666(7) Uani 1 1 d . . . . .
H20 H -0.2324 0.7784 0.4386 0.080 Uiso 1 1 calc R . . . .
C21 C -0.3170(3) 0.9331(3) 0.5360(2) 0.0722(7) Uani 1 1 d . . . . .
H21 H -0.3726 0.8905 0.5891 0.087 Uiso 1 1 calc R . . . .
C22 C -0.3229(3) 1.0683(3) 0.5494(2) 0.0678(7) Uani 1 1 d . . . . .
C23 C -0.2362(3) 1.1316(3) 0.4703(2) 0.0605(6) Uani 1 1 d . . . . .
C24 C -0.2476(3) 1.2692(3) 0.4804(3) 0.0742(8) Uani 1 1 d . . . . .
H24 H -0.1903 1.3115 0.4290 0.089 Uiso 1 1 calc R . . . .
C25 C -0.3428(4) 1.3398(3) 0.5654(3) 0.0867(9) Uani 1 1 d . . . . .
H25 H -0.3510 1.4308 0.5707 0.104 Uiso 1 1 calc R . . . .
C26 C -0.4270(4) 1.2778(4) 0.6436(3) 0.0937(11) Uani 1 1 d . . . . .
H26 H -0.4909 1.3274 0.7012 0.112 Uiso 1 1 calc R . . . .
C27 C -0.4173(3) 1.1445(4) 0.6373(3) 0.0836(9) Uani 1 1 d . . . . .
H27 H -0.4735 1.1036 0.6914 0.100 Uiso 1 1 calc R . . . .
O1 O -0.0568(2) 1.11518(17) 0.31015(16) 0.0659(5) Uani 1 1 d . . . . .
O2 O 0.1091(2) 1.12025(19) 0.16372(18) 0.0830(6) 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
C1 C2 1.468(3) . ?
C1 O1 1.392(3) . ?
C1 O2 1.192(3) . ?
C2 C3 1.468(3) . ?
C2 C11 1.367(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.318(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.462(3) . ?
C5 C6 1.385(4) . ?
C5 C10 1.387(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.359(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.365(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.501(3) . ?
C11 C19 1.442(3) . ?
C12 C13 1.372(3) . ?
C12 C17 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(3) . ?
C18 C23 1.418(3) . ?
C18 O1 1.358(3) . ?
C19 C20 1.420(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.352(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.421(4) . ?
C22 C23 1.410(4) . ?
C22 C27 1.411(3) . ?
C23 C24 1.415(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.364(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.366(4) . ?
C27 H27 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
O1 C1 C2 116.1(2) . . ?
O2 C1 C2 128.2(2) . . ?
O2 C1 O1 115.7(2) . . ?
C1 C2 C3 118.4(2) . . ?
C11 C2 C1 120.1(2) . . ?
C11 C2 C3 121.5(2) . . ?
C2 C3 H3 115.4 . . ?
C4 C3 C2 129.3(2) . . ?
C4 C3 H3 115.4 . . ?
C3 C4 H4 116.9 . . ?
C3 C4 C5 126.3(3) . . ?
C5 C4 H4 116.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 C10 117.5(3) . . ?
C10 C5 C4 122.4(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.1(3) . . ?
C9 C10 H10 120.0 . . ?
C2 C11 C12 121.1(2) . . ?
C2 C11 C19 120.7(2) . . ?
C19 C11 C12 118.2(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 C17 118.1(2) . . ?
C17 C12 C11 121.3(2) . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 120.4(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C23 122.7(2) . . ?
O1 C18 C19 121.1(2) . . ?
O1 C18 C23 116.2(2) . . ?
C18 C19 C11 118.3(2) . . ?
C18 C19 C20 117.9(2) . . ?
C20 C19 C11 123.8(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 C27 118.5(3) . . ?
C27 C22 C21 122.0(3) . . ?
C22 C23 C18 117.6(2) . . ?
C22 C23 C24 119.4(2) . . ?
C24 C23 C18 123.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.6(3) . . ?
C27 C26 H26 119.7 . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C18 O1 C1 123.58(19) . . ?

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
C1 C2 C3 C4 9.0(4) . . . . ?
C1 C2 C11 C12 176.2(2) . . . . ?
C1 C2 C11 C19 -3.0(3) . . . . ?
C2 C1 O1 C18 1.2(3) . . . . ?
C2 C3 C4 C5 176.8(2) . . . . ?
C2 C11 C12 C13 -72.5(3) . . . . ?
C2 C11 C12 C17 107.1(3) . . . . ?
C2 C11 C19 C18 3.7(3) . . . . ?
C2 C11 C19 C20 -176.5(2) . . . . ?
C3 C2 C11 C12 -5.3(4) . . . . ?
C3 C2 C11 C19 175.5(2) . . . . ?
C3 C4 C5 C6 -167.2(3) . . . . ?
C3 C4 C5 C10 12.2(4) . . . . ?
C4 C5 C6 C7 177.4(3) . . . . ?
C4 C5 C10 C9 -179.2(3) . . . . ?
C5 C6 C7 C8 1.9(5) . . . . ?
C6 C5 C10 C9 0.2(5) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C10 -1.9(6) . . . . ?
C8 C9 C10 C5 1.7(6) . . . . ?
C10 C5 C6 C7 -2.0(5) . . . . ?
C11 C2 C3 C4 -169.5(2) . . . . ?
C11 C12 C13 C14 179.4(3) . . . . ?
C11 C12 C17 C16 -178.9(2) . . . . ?
C11 C19 C20 C21 180.0(2) . . . . ?
C12 C11 C19 C18 -175.5(2) . . . . ?
C12 C11 C19 C20 4.3(3) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C12 C17 C16 0.7(4) . . . . ?
C13 C14 C15 C16 1.3(6) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C17 C12 C13 C14 -0.2(5) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C18 C23 C24 C25 177.9(3) . . . . ?
C19 C11 C12 C13 106.7(3) . . . . ?
C19 C11 C12 C17 -73.7(3) . . . . ?
C19 C18 C23 C22 3.1(4) . . . . ?
C19 C18 C23 C24 -175.3(2) . . . . ?
C19 C18 O1 C1 -0.5(3) . . . . ?
C19 C20 C21 C22 2.0(4) . . . . ?
C20 C21 C22 C23 -1.2(4) . . . . ?
C20 C21 C22 C27 176.6(3) . . . . ?
C21 C22 C23 C18 -1.3(4) . . . . ?
C21 C22 C23 C24 177.2(2) . . . . ?
C21 C22 C27 C26 -176.5(3) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C23 C18 C19 C11 177.4(2) . . . . ?
C23 C18 C19 C20 -2.4(4) . . . . ?
C23 C18 O1 C1 -179.9(2) . . . . ?
C23 C22 C27 C26 1.4(4) . . . . ?
C23 C24 C25 C26 1.0(5) . . . . ?
C24 C25 C26 C27 -0.3(5) . . . . ?
C25 C26 C27 C22 -1.0(5) . . . . ?
C27 C22 C23 C18 -179.2(2) . . . . ?
C27 C22 C23 C24 -0.7(4) . . . . ?
O1 C1 C2 C3 -178.0(2) . . . . ?
O1 C1 C2 C11 0.6(3) . . . . ?
O1 C18 C19 C11 -2.0(3) . . . . ?
O1 C18 C19 C20 178.2(2) . . . . ?
O1 C18 C23 C22 -177.5(2) . . . . ?
O1 C18 C23 C24 4.1(4) . . . . ?
O2 C1 C2 C3 3.3(4) . . . . ?
O2 C1 C2 C11 -178.1(3) . . . . ?
O2 C1 O1 C18 -179.9(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_201808347
_database_code_depnum_ccdc_archive 'CCDC 1888680'
loop_
_audit_author_name
_audit_author_address
'Yabo Li'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-01-04 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;
_audit_creation_date             2018-08-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H17 F O2'
_chemical_formula_sum            'C24 H17 F O2'
_chemical_formula_weight         356.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N2
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'
F F 0.0727 0.0534 '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                   10.4181(5)
_cell_length_b                   9.8070(5)
_cell_length_c                   18.1210(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.548(4)
_cell_angle_gamma                90
_cell_volume                     1813.94(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1814
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0780
_cell_measurement_theta_min      4.9600
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6891
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.332
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -14.50   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 175

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00  -15.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   29.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000   30.0000 116

#__ type_ start__ end____ width___ exp.time_
  4 omega -102.00  -61.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00   97.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega   80.00  105.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   42.00  102.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 120

#__ type_ start__ end____ width___ exp.time_
  8 omega   47.00   74.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega  -29.00    3.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   87.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega  139.00  167.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00   69.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
 13 omega   51.00   77.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   92.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 108

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00   77.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   85.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
 17 omega   70.00   98.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 56

#__ type_ start__ end____ width___ exp.time_
 18 omega   50.00   89.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
 19 omega   41.00   99.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 116

#__ type_ start__ end____ width___ exp.time_
 20 omega   40.00  156.00   0.5000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   90.0000 232

#__ type_ start__ end____ width___ exp.time_
 21 omega  -34.00   10.00   0.5000    3.6000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1252546000
_diffrn_orient_matrix_UB_12      -0.0861670000
_diffrn_orient_matrix_UB_13      0.0223394000
_diffrn_orient_matrix_UB_21      -0.0293830000
_diffrn_orient_matrix_UB_22      -0.0696735000
_diffrn_orient_matrix_UB_23      -0.0777908000
_diffrn_orient_matrix_UB_31      0.0788998000
_diffrn_orient_matrix_UB_32      0.1113952000
_diffrn_orient_matrix_UB_33      -0.0312374000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2216
_reflns_number_total             3224
_reflns_odcompleteness_completeness 99.51
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.023
_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)+(0.0935P)²+0.2786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1846
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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
C1 C 1.0568(3) 0.2774(3) 0.48442(13) 0.0640(7) Uani 1 1 d . . . . .
C2 C 0.9832(2) 0.3235(3) 0.41083(12) 0.0546(6) Uani 1 1 d . . . . .
C3 C 0.8737(3) 0.2410(3) 0.37176(14) 0.0613(6) Uani 1 1 d . . . . .
H3 H 0.8309 0.2745 0.3253 0.074 Uiso 1 1 calc R . . . .
C4 C 0.8262(3) 0.1237(3) 0.39340(14) 0.0637(7) Uani 1 1 d . . . . .
H4 H 0.8619 0.0903 0.4411 0.076 Uiso 1 1 calc R . . . .
C5 C 0.7207(3) 0.0447(3) 0.34598(15) 0.0645(6) Uani 1 1 d . . . . .
C6 C 0.6744(4) 0.0719(3) 0.27025(17) 0.0833(9) Uani 1 1 d . . . . .
H6 H 0.7100 0.1447 0.2483 0.100 Uiso 1 1 calc R . . . .
C7 C 0.5794(4) -0.0038(4) 0.2272(2) 0.1031(13) Uani 1 1 d . . . . .
H7 H 0.5533 0.0153 0.1761 0.124 Uiso 1 1 calc R . . . .
C8 C 0.5207(4) -0.1097(4) 0.2591(3) 0.1046(12) Uani 1 1 d . . . . .
H8 H 0.4519 -0.1587 0.2305 0.126 Uiso 1 1 calc R . . . .
C9 C 0.5664(4) -0.1407(4) 0.3337(2) 0.0987(11) Uani 1 1 d . . . . .
H9 H 0.5306 -0.2136 0.3555 0.118 Uiso 1 1 calc R . . . .
C10 C 0.6650(4) -0.0640(4) 0.37614(19) 0.0869(9) Uani 1 1 d . . . . .
H10 H 0.6947 -0.0861 0.4266 0.104 Uiso 1 1 calc R . . . .
C11 C 1.0192(2) 0.4397(3) 0.37893(12) 0.0552(6) Uani 1 1 d . . . . .
C12 C 0.9474(3) 0.4878(3) 0.30308(12) 0.0566(6) Uani 1 1 d . . . . .
C13 C 0.9811(3) 0.4399(3) 0.23841(13) 0.0635(7) Uani 1 1 d . . . . .
H13 H 1.0490 0.3772 0.2420 0.076 Uiso 1 1 calc R . . . .
C14 C 0.9162(3) 0.4830(3) 0.16770(13) 0.0675(7) Uani 1 1 d . . . . .
H14 H 0.9406 0.4516 0.1241 0.081 Uiso 1 1 calc R . . . .
C15 C 0.8157(3) 0.5729(3) 0.16462(14) 0.0675(7) Uani 1 1 d . . . . .
C16 C 0.7793(3) 0.6236(4) 0.22690(16) 0.0783(8) Uani 1 1 d . . . . .
H16 H 0.7109 0.6860 0.2227 0.094 Uiso 1 1 calc R . . . .
C17 C 0.8461(3) 0.5805(3) 0.29713(14) 0.0694(7) Uani 1 1 d . . . . .
H17 H 0.8224 0.6142 0.3405 0.083 Uiso 1 1 calc R . . . .
C18 C 1.1306(2) 0.5177(3) 0.41630(13) 0.0585(6) Uani 1 1 d . . . . .
C19 C 1.2024(3) 0.4703(3) 0.48405(12) 0.0580(6) Uani 1 1 d . . . . .
C20 C 1.3129(3) 0.5384(3) 0.52297(15) 0.0690(7) Uani 1 1 d . . . . .
H20 H 1.3595 0.5026 0.5679 0.083 Uiso 1 1 calc R . . . .
C21 C 1.3532(3) 0.6580(3) 0.49534(16) 0.0719(8) Uani 1 1 d . . . . .
C22 C 1.2810(3) 0.7087(3) 0.42784(16) 0.0724(7) Uani 1 1 d . . . . .
H22 H 1.3063 0.7901 0.4087 0.087 Uiso 1 1 calc R . . . .
C23 C 1.1730(3) 0.6404(3) 0.38900(15) 0.0688(7) Uani 1 1 d . . . . .
H23 H 1.1272 0.6761 0.3438 0.083 Uiso 1 1 calc R . . . .
C24 C 1.4710(3) 0.7348(4) 0.53687(19) 0.0913(10) Uani 1 1 d . . . . .
H24A H 1.5419 0.6722 0.5531 0.137 Uiso 1 1 calc GR . . . .
H24B H 1.4494 0.7794 0.5799 0.137 Uiso 1 1 calc GR . . . .
H24C H 1.4968 0.8017 0.5040 0.137 Uiso 1 1 calc GR . . . .
F1 F 0.7516(2) 0.6149(3) 0.09556(9) 0.1067(7) Uani 1 1 d . . . . .
O1 O 1.1667(2) 0.3532(2) 0.51626(9) 0.0699(5) Uani 1 1 d . . . . .
O2 O 1.0338(2) 0.1830(2) 0.52068(11) 0.0860(7) 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
C1 C2 1.470(3) . ?
C1 O1 1.390(3) . ?
C1 O2 1.187(3) . ?
C2 C3 1.460(4) . ?
C2 C11 1.365(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.342(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.472(4) . ?
C5 C6 1.386(4) . ?
C5 C10 1.378(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.353(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.503(3) . ?
C11 C18 1.441(4) . ?
C12 C13 1.372(4) . ?
C12 C17 1.380(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.361(4) . ?
C15 C16 1.355(4) . ?
C15 F1 1.359(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(3) . ?
C18 C23 1.405(4) . ?
C19 C20 1.394(4) . ?
C19 O1 1.373(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(4) . ?
C21 C22 1.393(4) . ?
C21 C24 1.507(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(4) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 C1 C2 116.7(2) . . ?
O2 C1 C2 128.0(3) . . ?
O2 C1 O1 115.3(2) . . ?
C3 C2 C1 119.0(2) . . ?
C11 C2 C1 120.2(2) . . ?
C11 C2 C3 120.8(2) . . ?
C2 C3 H3 115.4 . . ?
C4 C3 C2 129.2(2) . . ?
C4 C3 H3 115.4 . . ?
C3 C4 H4 118.1 . . ?
C3 C4 C5 123.8(2) . . ?
C5 C4 H4 118.1 . . ?
C6 C5 C4 123.2(3) . . ?
C10 C5 C4 120.0(3) . . ?
C10 C5 C6 116.8(3) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.3(3) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 119.1 . . ?
C9 C10 C5 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C2 C11 C12 121.4(2) . . ?
C2 C11 C18 120.6(2) . . ?
C18 C11 C12 118.0(2) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 C17 118.8(2) . . ?
C17 C12 C11 120.7(2) . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 H14 121.2 . . ?
C16 C15 C14 123.0(2) . . ?
C16 C15 F1 119.2(3) . . ?
F1 C15 C14 117.8(3) . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.6(3) . . ?
C17 C16 H16 120.7 . . ?
C12 C17 C16 120.5(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C11 118.7(2) . . ?
C19 C18 C23 116.6(2) . . ?
C23 C18 C11 124.7(2) . . ?
C18 C19 C20 122.2(3) . . ?
O1 C19 C18 120.9(2) . . ?
O1 C19 C20 116.9(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 C24 121.5(3) . . ?
C22 C21 C24 120.2(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.3(3) . . ?
C22 C23 H23 119.4 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 O1 C1 122.80(19) . . ?

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
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C11 C12 178.8(2) . . . . ?
C1 C2 C11 C18 0.8(4) . . . . ?
C2 C1 O1 C19 3.9(4) . . . . ?
C2 C3 C4 C5 -175.2(3) . . . . ?
C2 C11 C12 C13 -86.2(3) . . . . ?
C2 C11 C12 C17 93.6(3) . . . . ?
C2 C11 C18 C19 1.8(4) . . . . ?
C2 C11 C18 C23 -178.1(3) . . . . ?
C3 C2 C11 C12 0.5(4) . . . . ?
C3 C2 C11 C18 -177.4(2) . . . . ?
C3 C4 C5 C6 10.5(5) . . . . ?
C3 C4 C5 C10 -170.8(3) . . . . ?
C4 C5 C6 C7 178.5(3) . . . . ?
C4 C5 C10 C9 -179.8(3) . . . . ?
C5 C6 C7 C8 2.6(6) . . . . ?
C6 C5 C10 C9 -1.1(5) . . . . ?
C6 C7 C8 C9 -3.7(7) . . . . ?
C7 C8 C9 C10 2.5(7) . . . . ?
C8 C9 C10 C5 -0.1(6) . . . . ?
C10 C5 C6 C7 -0.1(5) . . . . ?
C11 C2 C3 C4 178.7(3) . . . . ?
C11 C12 C13 C14 -179.9(3) . . . . ?
C11 C12 C17 C16 -179.4(3) . . . . ?
C11 C18 C19 C20 178.8(2) . . . . ?
C11 C18 C19 O1 -1.7(4) . . . . ?
C11 C18 C23 C22 -179.6(3) . . . . ?
C12 C11 C18 C19 -176.2(2) . . . . ?
C12 C11 C18 C23 3.8(4) . . . . ?
C12 C13 C14 C15 -1.3(4) . . . . ?
C13 C12 C17 C16 0.4(4) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C13 C14 C15 F1 -179.7(3) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C17 C12 C13 C14 0.3(4) . . . . ?
C18 C11 C12 C13 91.9(3) . . . . ?
C18 C11 C12 C17 -88.4(3) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C18 C19 O1 C1 -1.3(4) . . . . ?
C19 C18 C23 C22 0.4(4) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C19 C20 C21 C24 179.0(3) . . . . ?
C20 C19 O1 C1 178.3(2) . . . . ?
C20 C21 C22 C23 -0.9(5) . . . . ?
C21 C22 C23 C18 0.7(5) . . . . ?
C23 C18 C19 C20 -1.3(4) . . . . ?
C23 C18 C19 O1 178.3(2) . . . . ?
C24 C21 C22 C23 -179.9(3) . . . . ?
F1 C15 C16 C17 -179.6(3) . . . . ?
O1 C1 C2 C3 174.7(2) . . . . ?
O1 C1 C2 C11 -3.6(4) . . . . ?
O1 C19 C20 C21 -178.5(2) . . . . ?
O2 C1 C2 C3 -5.6(4) . . . . ?
O2 C1 C2 C11 176.1(3) . . . . ?
O2 C1 O1 C19 -175.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
