# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_k11005-jjw-b
_database_code_depnum_ccdc_archive 'CCDC 2082461'
loop_
_audit_author_name
_audit_author_address
'Vishal Kudale'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-03
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H22 F2 O4'
_chemical_formula_sum            'C31 H22 F2 O4'
_chemical_formula_weight         496.48
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8605(5)
_cell_length_b                   11.7131(10)
_cell_length_c                   13.7225(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.580(5)
_cell_angle_gamma                90
_cell_volume                     1259.41(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9704
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      26.5040
_cell_measurement_theta_min      2.2750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.0
_exptl_crystal_size_min          0.0
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16457
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.289
_diffrn_ambient_temperature      143(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00 100.00   0.50   13.63    --   10.60  77.00   0.00  230
  2  ω    -79.00  36.00   0.50   13.63    --   10.60 -77.00 120.00  230
  3  ω    -79.00  41.00   0.50   13.63    --   10.60 -57.00 -90.00  240
  4  ω    -15.00 100.00   0.50   13.63    --   10.60  77.00-180.00  230
  5  ω    -79.00  41.00   0.50   13.63    --   10.60 -57.00-120.00  240
  6  ω    -17.00 100.00   0.50   13.63    --   10.60  82.00  60.00  234
  7  ω    -79.00  41.00   0.50   13.63    --   10.60 -57.00   0.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0686750000
_diffrn_orient_matrix_UB_12      -0.0162300000
_diffrn_orient_matrix_UB_13      -0.0277134000
_diffrn_orient_matrix_UB_21      -0.0457944000
_diffrn_orient_matrix_UB_22      0.0212102000
_diffrn_orient_matrix_UB_23      -0.0429828000
_diffrn_orient_matrix_UB_31      0.0372668000
_diffrn_orient_matrix_UB_32      0.0543387000
_diffrn_orient_matrix_UB_33      0.0085301000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                3603
_reflns_number_total             4297
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.7(14)
_refine_ls_extinction_coef       0.028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     955
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.000
_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)+(0.1032P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1473
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.7(14)
 -0.7(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim O1 \\sim O2
\\sim O3 \\sim O4 \\sim F1 \\sim F2: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
4.a Ternary CH refined with riding coordinates:
 C2(H2), C17(H17)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5476(3) 0.9767(2) 0.2871(2) 0.0627(8) Uani 1 1 d . U . . .
F2 F 0.9822(6) 0.0663(4) 0.6797(3) 0.1209(16) Uani 1 1 d . U . . .
O1 O 0.5210(4) 0.5161(3) 0.05329(18) 0.0511(8) Uani 1 1 d . U . . .
O2 O 0.5982(4) 0.2485(3) 0.1283(2) 0.0518(8) Uani 1 1 d . U . . .
O3 O 0.6100(4) 0.4551(3) 0.43388(18) 0.0506(8) Uani 1 1 d . U . . .
O4 O 0.2740(4) 0.3016(3) 0.44921(18) 0.0504(8) Uani 1 1 d . U . . .
C1 C 0.4495(5) 0.3928(4) 0.2561(2) 0.0390(9) Uani 1 1 d . U . . .
H1A H 0.399425 0.459209 0.284842 0.047 Uiso 1 1 calc R U . . .
H1B H 0.366161 0.362421 0.206833 0.047 Uiso 1 1 calc R U . . .
C2 C 0.6095(5) 0.4303(4) 0.2061(3) 0.0388(9) Uani 1 1 d . U . . .
H2 H 0.698892 0.453245 0.256128 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5604(5) 0.5329(4) 0.1399(2) 0.0403(9) Uani 1 1 d . U . . .
C4 C 0.5571(5) 0.6492(4) 0.1823(3) 0.0375(9) Uani 1 1 d . U . . .
C5 C 0.5989(5) 0.6728(4) 0.2807(3) 0.0419(9) Uani 1 1 d . U . . .
H5 H 0.629328 0.613260 0.323461 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5960(5) 0.7829(4) 0.3160(3) 0.0446(10) Uani 1 1 d . U . . .
H6 H 0.625102 0.798435 0.381654 0.053 Uiso 1 1 calc R U . . .
C7 C 0.5491(5) 0.8687(4) 0.2516(3) 0.0434(9) Uani 1 1 d . U . . .
C8 C 0.5041(5) 0.8504(4) 0.1541(3) 0.0455(10) Uani 1 1 d . U . . .
H8 H 0.471693 0.910669 0.112556 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5083(5) 0.7399(4) 0.1196(3) 0.0398(9) Uani 1 1 d . U . . .
H9 H 0.478416 0.725448 0.053798 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6768(5) 0.3365(4) 0.1438(2) 0.0402(9) Uani 1 1 d . U . . .
C11 C 0.8440(5) 0.3545(4) 0.1011(3) 0.0404(9) Uani 1 1 d . U . . .
C12 C 0.9406(5) 0.4542(4) 0.1175(3) 0.0464(10) Uani 1 1 d . U . . .
H12 H 0.900369 0.512508 0.155486 0.056 Uiso 1 1 calc R U . . .
C13 C 1.0938(5) 0.4659(5) 0.0780(3) 0.0525(11) Uani 1 1 d . U . . .
H13 H 1.158211 0.531902 0.089311 0.063 Uiso 1 1 calc R U . . .
C14 C 1.1530(6) 0.3785(5) 0.0205(3) 0.0564(12) Uani 1 1 d . U . . .
H14 H 1.257240 0.386623 -0.006334 0.068 Uiso 1 1 calc R U . . .
C15 C 1.0608(6) 0.2822(5) 0.0034(3) 0.0628(13) Uani 1 1 d . U . . .
H15 H 1.101416 0.224923 -0.035580 0.075 Uiso 1 1 calc R U . . .
C16 C 0.9055(5) 0.2683(5) 0.0439(3) 0.0528(11) Uani 1 1 d . U . . .
H16 H 0.842979 0.201535 0.032786 0.063 Uiso 1 1 calc R U . . .
C17 C 0.4870(5) 0.3019(4) 0.3362(2) 0.0393(9) Uani 1 1 d . U . . .
H17 H 0.545697 0.236762 0.309149 0.047 Uiso 1 1 calc R U . . .
C18 C 0.5988(5) 0.3525(4) 0.4233(3) 0.0422(9) Uani 1 1 d . U . . .
C19 C 0.6948(5) 0.2723(4) 0.4927(3) 0.0422(9) Uani 1 1 d . U . . .
C20 C 0.6733(5) 0.1565(4) 0.4890(3) 0.0470(10) Uani 1 1 d . U . . .
H20 H 0.593108 0.125405 0.443055 0.056 Uiso 1 1 calc R U . . .
C21 C 0.7685(6) 0.0846(5) 0.5524(3) 0.0568(12) Uani 1 1 d . U . . .
H21 H 0.754353 0.005770 0.549726 0.068 Uiso 1 1 calc R U . . .
C22 C 0.8851(7) 0.1351(5) 0.6194(4) 0.0679(14) Uani 1 1 d . U . . .
C23 C 0.9077(7) 0.2512(6) 0.6267(4) 0.0706(14) Uani 1 1 d . U . . .
H23 H 0.986439 0.282614 0.673345 0.085 Uiso 1 1 calc R U . . .
C24 C 0.8107(6) 0.3188(5) 0.5632(3) 0.0559(12) Uani 1 1 d . U . . .
H24 H 0.822590 0.397734 0.567356 0.067 Uiso 1 1 calc R U . . .
C25 C 0.3192(5) 0.2626(4) 0.3728(2) 0.0407(9) Uani 1 1 d . U . . .
C26 C 0.2089(5) 0.1791(4) 0.3151(3) 0.0398(9) Uani 1 1 d . U . . .
C27 C 0.2523(5) 0.1323(4) 0.2274(3) 0.0438(10) Uani 1 1 d . U . . .
H27 H 0.354578 0.152114 0.202037 0.053 Uiso 1 1 calc R U . . .
C28 C 0.1415(6) 0.0557(5) 0.1779(3) 0.0529(11) Uani 1 1 d . U . . .
H28 H 0.168138 0.025576 0.118295 0.064 Uiso 1 1 calc R U . . .
C29 C -0.0067(6) 0.0244(5) 0.2165(4) 0.0637(13) Uani 1 1 d . U . . .
H29 H -0.078351 -0.028438 0.183515 0.076 Uiso 1 1 calc R U . . .
C30 C -0.0514(6) 0.0695(5) 0.3027(4) 0.0647(13) Uani 1 1 d . U . . .
H30 H -0.153470 0.048681 0.327731 0.078 Uiso 1 1 calc R U . . .
C31 C 0.0582(6) 0.1470(5) 0.3527(3) 0.0545(11) Uani 1 1 d . U . . .
H31 H 0.029678 0.177353 0.411829 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C7 1.355(5) . ?
F2 C22 1.347(6) . ?
O1 C3 1.220(4) . ?
O2 C10 1.212(5) . ?
O3 C18 1.213(6) . ?
O4 C25 1.222(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.543(5) . ?
C1 C17 1.542(6) . ?
C2 H2 0.9800 . ?
C2 C3 1.537(6) . ?
C2 C10 1.513(6) . ?
C3 C4 1.482(6) . ?
C4 C5 1.393(5) . ?
C4 C9 1.402(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.369(6) . ?
C7 C8 1.374(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.496(6) . ?
C11 C12 1.401(6) . ?
C11 C16 1.388(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.351(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9800 . ?
C17 C18 1.544(5) . ?
C17 C25 1.520(6) . ?
C18 C19 1.498(6) . ?
C19 C20 1.366(7) . ?
C19 C24 1.387(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(7) . ?
C22 C23 1.374(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.364(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.492(6) . ?
C26 C27 1.390(6) . ?
C26 C31 1.381(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.367(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.367(7) . ?
C30 H30 0.9300 . ?
C30 C31 1.394(7) . ?
C31 H31 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
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C17 C1 H1A 108.9 . . ?
C17 C1 H1B 108.9 . . ?
C17 C1 C2 113.4(3) . . ?
C1 C2 H2 109.4 . . ?
C3 C2 C1 108.1(3) . . ?
C3 C2 H2 109.4 . . ?
C10 C2 C1 112.3(3) . . ?
C10 C2 H2 109.4 . . ?
C10 C2 C3 108.4(3) . . ?
O1 C3 C2 118.8(4) . . ?
O1 C3 C4 121.3(4) . . ?
C4 C3 C2 119.8(3) . . ?
C5 C4 C3 123.6(4) . . ?
C5 C4 C9 118.5(4) . . ?
C9 C4 C3 117.9(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.9 . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 H6 120.9 . . ?
F1 C7 C6 117.6(4) . . ?
F1 C7 C8 119.1(4) . . ?
C6 C7 C8 123.3(4) . . ?
C7 C8 H8 121.0 . . ?
C7 C8 C9 118.0(4) . . ?
C9 C8 H8 121.0 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.9(3) . . ?
C8 C9 H9 119.5 . . ?
O2 C10 C2 121.4(4) . . ?
O2 C10 C11 120.1(4) . . ?
C11 C10 C2 118.5(4) . . ?
C12 C11 C10 122.4(4) . . ?
C16 C11 C10 118.4(4) . . ?
C16 C11 C12 119.2(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(5) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 119.8(5) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C1 C17 H17 109.6 . . ?
C1 C17 C18 110.6(4) . . ?
C18 C17 H17 109.6 . . ?
C25 C17 C1 108.8(3) . . ?
C25 C17 H17 109.6 . . ?
C25 C17 C18 108.4(3) . . ?
O3 C18 C17 120.2(4) . . ?
O3 C18 C19 121.2(4) . . ?
C19 C18 C17 118.6(4) . . ?
C20 C19 C18 123.0(4) . . ?
C20 C19 C24 119.2(4) . . ?
C24 C19 C18 117.8(4) . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 121.5 . . ?
C22 C21 C20 117.0(5) . . ?
C22 C21 H21 121.5 . . ?
F2 C22 C21 117.8(5) . . ?
F2 C22 C23 118.9(5) . . ?
C23 C22 C21 123.2(4) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 C22 117.8(5) . . ?
C24 C23 H23 121.1 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.3(5) . . ?
C23 C24 H24 119.4 . . ?
O4 C25 C17 119.3(4) . . ?
O4 C25 C26 120.3(4) . . ?
C26 C25 C17 120.4(3) . . ?
C27 C26 C25 123.0(4) . . ?
C31 C26 C25 117.4(4) . . ?
C31 C26 C27 119.6(4) . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.3(4) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.3(4) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.2(4) . . ?
C30 C29 H29 119.4 . . ?
C29 C30 H30 120.5 . . ?
C29 C30 C31 119.1(5) . . ?
C31 C30 H30 120.5 . . ?
C26 C31 C30 120.6(4) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?

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
F1 C7 C8 C9 179.4(4) . . . . ?
F2 C22 C23 C24 178.4(5) . . . . ?
O1 C3 C4 C5 179.3(3) . . . . ?
O1 C3 C4 C9 -0.5(5) . . . . ?
O2 C10 C11 C12 -179.4(4) . . . . ?
O2 C10 C11 C16 0.0(5) . . . . ?
O3 C18 C19 C20 173.5(4) . . . . ?
O3 C18 C19 C24 -6.7(6) . . . . ?
O4 C25 C26 C27 179.5(4) . . . . ?
O4 C25 C26 C31 -1.4(6) . . . . ?
C1 C2 C3 O1 -95.8(4) . . . . ?
C1 C2 C3 C4 82.5(4) . . . . ?
C1 C2 C10 O2 7.8(5) . . . . ?
C1 C2 C10 C11 -172.2(3) . . . . ?
C1 C17 C18 O3 18.2(5) . . . . ?
C1 C17 C18 C19 -160.7(3) . . . . ?
C1 C17 C25 O4 -100.0(4) . . . . ?
C1 C17 C25 C26 78.7(5) . . . . ?
C2 C1 C17 C18 66.8(4) . . . . ?
C2 C1 C17 C25 -174.2(3) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C2 C3 C4 C9 -178.7(3) . . . . ?
C2 C10 C11 C12 0.6(5) . . . . ?
C2 C10 C11 C16 180.0(3) . . . . ?
C3 C2 C10 O2 -111.5(4) . . . . ?
C3 C2 C10 C11 68.5(4) . . . . ?
C3 C4 C5 C6 179.0(4) . . . . ?
C3 C4 C9 C8 -179.4(4) . . . . ?
C4 C5 C6 C7 0.6(6) . . . . ?
C5 C4 C9 C8 0.9(5) . . . . ?
C5 C6 C7 F1 -179.7(4) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 C4 0.0(6) . . . . ?
C9 C4 C5 C6 -1.2(5) . . . . ?
C10 C2 C3 O1 26.0(5) . . . . ?
C10 C2 C3 C4 -155.6(3) . . . . ?
C10 C11 C12 C13 179.1(4) . . . . ?
C10 C11 C16 C15 -179.8(4) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C12 C11 C16 C15 -0.4(6) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
C14 C15 C16 C11 0.9(7) . . . . ?
C16 C11 C12 C13 -0.2(6) . . . . ?
C17 C1 C2 C3 -171.4(3) . . . . ?
C17 C1 C2 C10 69.1(4) . . . . ?
C17 C18 C19 C20 -7.6(5) . . . . ?
C17 C18 C19 C24 172.2(4) . . . . ?
C17 C25 C26 C27 0.8(6) . . . . ?
C17 C25 C26 C31 179.9(4) . . . . ?
C18 C17 C25 O4 20.4(5) . . . . ?
C18 C17 C25 C26 -160.9(4) . . . . ?
C18 C19 C20 C21 177.8(4) . . . . ?
C18 C19 C24 C23 -177.5(4) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C20 C19 C24 C23 2.3(7) . . . . ?
C20 C21 C22 F2 -178.1(5) . . . . ?
C20 C21 C22 C23 1.1(8) . . . . ?
C21 C22 C23 C24 -0.8(9) . . . . ?
C22 C23 C24 C19 -0.9(8) . . . . ?
C24 C19 C20 C21 -2.0(6) . . . . ?
C25 C17 C18 O3 -101.1(4) . . . . ?
C25 C17 C18 C19 80.0(4) . . . . ?
C25 C26 C27 C28 -179.5(4) . . . . ?
C25 C26 C31 C30 179.9(4) . . . . ?
C26 C27 C28 C29 -1.7(7) . . . . ?
C27 C26 C31 C30 -0.9(7) . . . . ?
C27 C28 C29 C30 1.7(8) . . . . ?
C28 C29 C30 C31 -1.2(9) . . . . ?
C29 C30 C31 C26 0.8(8) . . . . ?
C31 C26 C27 C28 1.3(6) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.666
_oxdiff_exptl_absorpt_empirical_full_min 0.505
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.7(14)
2 -0.7(14)

####################################################################### 
# 
# 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_k11004-jjw-d
_database_code_depnum_ccdc_archive 'CCDC 2082727'
loop_
_audit_author_name
_audit_author_address
'Vishal Kudale'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2021-05-08 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-04-21
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H21 N O2'
_chemical_formula_sum            'C31 H21 N O2'
_chemical_formula_weight         439.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.98540(10)
_cell_length_b                   20.6879(4)
_cell_length_c                   18.0213(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.780(2)
_cell_angle_gamma                90
_cell_volume                     2220.15(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16095
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9560
_cell_measurement_theta_min      1.9680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25693
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.035
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00 100.00   0.50    8.65    --   10.60  57.00 -60.00  240
  2  ω    -20.00 100.00   0.50    8.65    --   10.60  57.00 120.00  240
  3  ω    -15.00 100.00   0.50    8.65    --   10.60  77.00 -60.00  230
  4  ω    -79.00  38.00   0.50    8.65    --   10.60 -82.00 -30.00  234
  5  ω   -100.00  15.00   0.50    8.65    --  -10.90 -77.00   0.00  230
  6  ω    -30.00  20.00   0.50    8.65    --  -10.90 -57.00  30.00  100
  7  ω     16.00  52.00   0.50    8.65    --  -10.90  38.00 -60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1051128000
_diffrn_orient_matrix_UB_12      -0.0146274000
_diffrn_orient_matrix_UB_13      -0.0042411000
_diffrn_orient_matrix_UB_21      -0.0560461000
_diffrn_orient_matrix_UB_22      -0.0269721000
_diffrn_orient_matrix_UB_23      -0.0176421000
_diffrn_orient_matrix_UB_31      0.0018124000
_diffrn_orient_matrix_UB_32      0.0153083000
_diffrn_orient_matrix_UB_33      -0.0351434000
_diffrn_oxdiff_digest_frames     
;
01b1b68829f8b2d8d65156215ba76a75e6000258f9a
;
_diffrn_oxdiff_digest_hkl        
;
01b80ea9874e6197b47a0f2205edb0d23cd341
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4037
_reflns_number_total             4684
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.067
_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)+(0.0446P)²+0.5723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0935
_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), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.27163(14) 0.44893(4) 0.36189(6) 0.0311(2) Uani 1 1 d . . . . .
O2 O 0.45622(13) 0.28565(4) 0.47360(5) 0.0240(2) Uani 1 1 d . . . . .
N1 N 0.58921(15) 0.36704(4) 0.26600(5) 0.0172(2) Uani 1 1 d . . . . .
C1 C 0.75130(17) 0.41139(5) 0.28040(6) 0.0166(2) Uani 1 1 d . . . . .
C2 C 0.89593(17) 0.41116(5) 0.34626(6) 0.0172(2) Uani 1 1 d . . . . .
C3 C 0.86787(18) 0.36366(5) 0.39870(6) 0.0187(2) Uani 1 1 d . . . . .
H3 H 0.964298 0.361685 0.442455 0.022 Uiso 1 1 calc R . . . .
C4 C 0.69511(18) 0.31899(5) 0.38566(6) 0.0173(2) Uani 1 1 d . . . . .
C5 C 0.56093(18) 0.32136(5) 0.31713(6) 0.0163(2) Uani 1 1 d . . . . .
C6 C 0.77415(18) 0.45930(5) 0.21976(6) 0.0175(2) Uani 1 1 d . . . . .
C7 C 0.59364(19) 0.49806(6) 0.19347(7) 0.0233(3) Uani 1 1 d . . . . .
H7 H 0.460230 0.495784 0.215705 0.028 Uiso 1 1 calc R . . . .
C8 C 0.6107(2) 0.54002(6) 0.13447(7) 0.0280(3) Uani 1 1 d . . . . .
H8 H 0.489629 0.566249 0.117938 0.034 Uiso 1 1 calc R . . . .
C9 C 0.8068(2) 0.54320(6) 0.09992(7) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.816749 0.570884 0.059726 0.032 Uiso 1 1 calc R . . . .
C10 C 0.9874(2) 0.50498(6) 0.12554(7) 0.0253(3) Uani 1 1 d . . . . .
H10 H 1.119241 0.506711 0.102360 0.030 Uiso 1 1 calc R . . . .
C11 C 0.97266(19) 0.46388(6) 0.18596(7) 0.0214(3) Uani 1 1 d . . . . .
H11 H 1.096456 0.439256 0.203920 0.026 Uiso 1 1 calc R . . . .
C12 C 1.07366(18) 0.46232(6) 0.36215(6) 0.0189(2) Uani 1 1 d . . . . .
C13 C 0.99626(18) 0.52858(6) 0.37865(6) 0.0180(2) Uani 1 1 d . . . . .
C14 C 0.79001(19) 0.53933(6) 0.40625(7) 0.0244(3) Uani 1 1 d . . . . .
H14 H 0.694072 0.504866 0.412667 0.029 Uiso 1 1 calc R . . . .
C15 C 0.7285(2) 0.60157(6) 0.42408(7) 0.0272(3) Uani 1 1 d . . . . .
H15 H 0.593738 0.608536 0.444377 0.033 Uiso 1 1 calc R . . . .
C16 C 0.8660(2) 0.65333(6) 0.41193(7) 0.0248(3) Uani 1 1 d . . . . .
H16 H 0.822388 0.695065 0.423127 0.030 Uiso 1 1 calc R . . . .
C17 C 1.0693(2) 0.64301(6) 0.38302(7) 0.0262(3) Uani 1 1 d . . . . .
H17 H 1.160795 0.677880 0.374023 0.031 Uiso 1 1 calc R . . . .
C18 C 1.1356(2) 0.58085(6) 0.36758(6) 0.0225(3) Uani 1 1 d . . . . .
H18 H 1.274072 0.573915 0.349705 0.027 Uiso 1 1 calc R . . . .
C19 C 0.63609(18) 0.27689(5) 0.44903(6) 0.0178(2) Uani 1 1 d . . . . .
C20 C 0.79939(18) 0.22836(5) 0.48236(6) 0.0178(2) Uani 1 1 d . . . . .
C21 C 0.99406(19) 0.21289(5) 0.44994(6) 0.0191(2) Uani 1 1 d . . . . .
H21 H 1.024972 0.233139 0.406052 0.023 Uiso 1 1 calc R . . . .
C22 C 1.1421(2) 0.16723(6) 0.48314(7) 0.0231(3) Uani 1 1 d . . . . .
H22 H 1.271623 0.156740 0.461299 0.028 Uiso 1 1 calc R . . . .
C23 C 1.0970(2) 0.13735(6) 0.54863(7) 0.0275(3) Uani 1 1 d . . . . .
H23 H 1.196468 0.106789 0.570732 0.033 Uiso 1 1 calc R . . . .
C24 C 0.9037(2) 0.15280(6) 0.58156(7) 0.0280(3) Uani 1 1 d . . . . .
H24 H 0.874749 0.132916 0.625871 0.034 Uiso 1 1 calc R . . . .
C25 C 0.7550(2) 0.19759(6) 0.54854(6) 0.0225(3) Uani 1 1 d . . . . .
H25 H 0.624652 0.207435 0.570270 0.027 Uiso 1 1 calc R . . . .
C26 C 0.38552(18) 0.27206(5) 0.29555(6) 0.0170(2) Uani 1 1 d . . . . .
C27 C 0.42314(19) 0.20667(5) 0.31094(6) 0.0184(2) Uani 1 1 d . . . . .
H27 H 0.559584 0.193483 0.335534 0.022 Uiso 1 1 calc R . . . .
C28 C 0.2589(2) 0.16118(6) 0.28990(6) 0.0217(3) Uani 1 1 d . . . . .
H28 H 0.285895 0.117692 0.300333 0.026 Uiso 1 1 calc R . . . .
C29 C 0.0544(2) 0.18022(6) 0.25334(6) 0.0227(3) Uani 1 1 d . . . . .
H29 H -0.056727 0.149713 0.240180 0.027 Uiso 1 1 calc R . . . .
C30 C 0.01653(19) 0.24488(6) 0.23655(6) 0.0224(3) Uani 1 1 d . . . . .
H30 H -0.119362 0.257793 0.211341 0.027 Uiso 1 1 calc R . . . .
C31 C 0.18116(18) 0.29034(6) 0.25730(6) 0.0191(2) Uani 1 1 d . . . . .
H31 H 0.154967 0.333636 0.245562 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.2173(14) . ?
O2 C19 1.2182(14) . ?
N1 C1 1.3415(14) . ?
N1 C5 1.3424(14) . ?
C1 C2 1.3969(15) . ?
C1 C6 1.4917(15) . ?
C2 C3 1.3852(16) . ?
C2 C12 1.5076(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.3891(15) . ?
C4 C5 1.4045(15) . ?
C4 C19 1.5063(15) . ?
C5 C26 1.4872(15) . ?
C6 C7 1.3899(16) . ?
C6 C11 1.3918(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.3843(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3843(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3810(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.3913(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.4864(16) . ?
C13 C14 1.3945(16) . ?
C13 C18 1.3923(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.3857(18) . ?
C15 H15 0.9300 . ?
C15 C16 1.3814(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3872(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.3823(17) . ?
C18 H18 0.9300 . ?
C19 C20 1.4852(16) . ?
C20 C21 1.3922(16) . ?
C20 C25 1.4007(16) . ?
C21 H21 0.9300 . ?
C21 C22 1.3885(16) . ?
C22 H22 0.9300 . ?
C22 C23 1.3828(17) . ?
C23 H23 0.9300 . ?
C23 C24 1.3897(18) . ?
C24 H24 0.9300 . ?
C24 C25 1.3779(17) . ?
C25 H25 0.9300 . ?
C26 C27 1.3946(16) . ?
C26 C31 1.3944(15) . ?
C27 H27 0.9300 . ?
C27 C28 1.3859(16) . ?
C28 H28 0.9300 . ?
C28 C29 1.3875(17) . ?
C29 H29 0.9300 . ?
C29 C30 1.3852(17) . ?
C30 H30 0.9300 . ?
C30 C31 1.3861(16) . ?
C31 H31 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
C1 N1 C5 119.18(10) . . ?
N1 C1 C2 122.42(10) . . ?
N1 C1 C6 115.51(9) . . ?
C2 C1 C6 122.01(10) . . ?
C1 C2 C12 121.60(10) . . ?
C3 C2 C1 118.35(10) . . ?
C3 C2 C12 120.02(10) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.72(10) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 118.39(10) . . ?
C3 C4 C19 118.93(10) . . ?
C5 C4 C19 122.00(10) . . ?
N1 C5 C4 121.85(10) . . ?
N1 C5 C26 115.97(9) . . ?
C4 C5 C26 122.14(10) . . ?
C7 C6 C1 120.50(10) . . ?
C7 C6 C11 118.69(10) . . ?
C11 C6 C1 120.73(10) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.58(11) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.45(11) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.54(11) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.16(11) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.7 . . ?
C10 C11 C6 120.55(11) . . ?
C10 C11 H11 119.7 . . ?
O1 C12 C2 120.53(10) . . ?
O1 C12 C13 122.25(10) . . ?
C13 C12 C2 117.21(9) . . ?
C14 C13 C12 121.56(10) . . ?
C18 C13 C12 118.97(10) . . ?
C18 C13 C14 119.46(11) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.75(11) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.48(11) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.94(11) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.96(11) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.35(11) . . ?
C17 C18 H18 119.8 . . ?
O2 C19 C4 118.22(10) . . ?
O2 C19 C20 121.56(10) . . ?
C20 C19 C4 120.16(9) . . ?
C21 C20 C19 122.02(10) . . ?
C21 C20 C25 119.44(11) . . ?
C25 C20 C19 118.55(10) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.01(11) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.07(11) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.26(12) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.99(11) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.23(11) . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C5 121.18(10) . . ?
C31 C26 C5 120.28(10) . . ?
C31 C26 C27 118.52(10) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.55(11) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.32(11) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.2 . . ?
C30 C29 C28 119.66(11) . . ?
C30 C29 H29 120.2 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.01(11) . . ?
C31 C30 H30 120.0 . . ?
C26 C31 H31 119.5 . . ?
C30 C31 C26 120.91(11) . . ?
C30 C31 H31 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C13 C14 -155.43(12) . . . . ?
O1 C12 C13 C18 23.28(17) . . . . ?
O2 C19 C20 C21 172.83(11) . . . . ?
O2 C19 C20 C25 -7.34(16) . . . . ?
N1 C1 C2 C3 -0.81(16) . . . . ?
N1 C1 C2 C12 -178.59(10) . . . . ?
N1 C1 C6 C7 58.00(14) . . . . ?
N1 C1 C6 C11 -118.85(12) . . . . ?
N1 C5 C26 C27 137.12(11) . . . . ?
N1 C5 C26 C31 -41.00(14) . . . . ?
C1 N1 C5 C4 0.56(16) . . . . ?
C1 N1 C5 C26 -177.08(9) . . . . ?
C1 C2 C3 C4 -1.69(16) . . . . ?
C1 C2 C12 O1 -110.06(13) . . . . ?
C1 C2 C12 C13 70.58(14) . . . . ?
C1 C6 C7 C8 -176.45(11) . . . . ?
C1 C6 C11 C10 174.91(11) . . . . ?
C2 C1 C6 C7 -124.77(12) . . . . ?
C2 C1 C6 C11 58.38(15) . . . . ?
C2 C3 C4 C5 3.49(16) . . . . ?
C2 C3 C4 C19 -167.27(10) . . . . ?
C2 C12 C13 C14 23.93(15) . . . . ?
C2 C12 C13 C18 -157.37(10) . . . . ?
C3 C2 C12 O1 72.20(15) . . . . ?
C3 C2 C12 C13 -107.17(12) . . . . ?
C3 C4 C5 N1 -2.99(16) . . . . ?
C3 C4 C5 C26 174.50(10) . . . . ?
C3 C4 C19 O2 111.35(12) . . . . ?
C3 C4 C19 C20 -65.80(14) . . . . ?
C4 C5 C26 C27 -40.50(15) . . . . ?
C4 C5 C26 C31 141.37(11) . . . . ?
C4 C19 C20 C21 -10.12(16) . . . . ?
C4 C19 C20 C25 169.71(10) . . . . ?
C5 N1 C1 C2 1.38(16) . . . . ?
C5 N1 C1 C6 178.60(9) . . . . ?
C5 C4 C19 O2 -59.06(15) . . . . ?
C5 C4 C19 C20 123.78(11) . . . . ?
C5 C26 C27 C28 -179.41(10) . . . . ?
C5 C26 C31 C30 179.72(10) . . . . ?
C6 C1 C2 C3 -177.85(10) . . . . ?
C6 C1 C2 C12 4.36(16) . . . . ?
C6 C7 C8 C9 1.11(19) . . . . ?
C7 C6 C11 C10 -2.00(17) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C11 -0.39(19) . . . . ?
C9 C10 C11 C6 1.98(18) . . . . ?
C11 C6 C7 C8 0.46(18) . . . . ?
C12 C2 C3 C4 176.13(10) . . . . ?
C12 C13 C14 C15 177.09(11) . . . . ?
C12 C13 C18 C17 -179.44(11) . . . . ?
C13 C14 C15 C16 2.59(19) . . . . ?
C14 C13 C18 C17 -0.71(17) . . . . ?
C14 C15 C16 C17 -1.25(19) . . . . ?
C15 C16 C17 C18 -1.08(18) . . . . ?
C16 C17 C18 C13 2.06(18) . . . . ?
C18 C13 C14 C15 -1.60(17) . . . . ?
C19 C4 C5 N1 167.48(10) . . . . ?
C19 C4 C5 C26 -15.04(16) . . . . ?
C19 C20 C21 C22 179.94(10) . . . . ?
C19 C20 C25 C24 -179.31(11) . . . . ?
C20 C21 C22 C23 -0.38(17) . . . . ?
C21 C20 C25 C24 0.53(17) . . . . ?
C21 C22 C23 C24 0.00(19) . . . . ?
C22 C23 C24 C25 0.64(19) . . . . ?
C23 C24 C25 C20 -0.90(19) . . . . ?
C25 C20 C21 C22 0.11(16) . . . . ?
C26 C27 C28 C29 -0.16(17) . . . . ?
C27 C26 C31 C30 1.54(16) . . . . ?
C27 C28 C29 C30 1.32(17) . . . . ?
C28 C29 C30 C31 -1.03(17) . . . . ?
C29 C30 C31 C26 -0.41(17) . . . . ?
C31 C26 C27 C28 -1.26(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.812
