# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2026

####################################################################### 
# 
# 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_nq01
_audit_block_doi                 10.5517/ccdc.csd.cc2mkxmr
_database_code_depnum_ccdc_archive 'CCDC 2430295'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2026-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H18 N2 O'
_chemical_formula_sum            'C32 H18 N2 O'
_chemical_formula_weight         446.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C32H20N2O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.4359(3)
_cell_length_b                   15.9420(6)
_cell_length_c                   21.1245(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4188.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5444
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      76.6280
_cell_measurement_theta_min      4.1890
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
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    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1856
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 13 0.0783
-8 0 0 0.0616
8 0 0 0.0616
0 10 -3 0.0093
0 -10 3 0.0093
0 -2 -13 0.0130

_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.019
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.5248 2.4457 13.2956 -0.0312 -0.0227 -0.9993
-8.0669 0.1722 -0.2356 -0.5655 0.8231 -0.0515
8.0669 -0.1722 0.2356 0.5655 -0.8231 0.0515
0.1448 10.1309 -2.8121 -0.8241 -0.5663 0.0090
-0.1448 -10.1309 2.8121 0.8241 0.5663 -0.0090
0.4657 -2.0553 -13.4163 -0.0051 0.0075 1.0000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21301
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.189
_diffrn_reflns_theta_min         4.186
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  19.00   0.50   35.00    --  -48.45  16.00 100.00   66
  2  ω    -23.00  19.00   0.50   35.00    --   48.45 -16.00 -69.00   84
  3  ω   -151.00-110.00   0.50  100.00    --  -90.00-126.00  84.00   82
  4  ω     41.00 104.00   0.50  100.00    --  111.50-111.00 167.00  126
  5  ω    104.00 152.00   0.50  100.00    --  111.50  16.00 100.00   96
  6  ω    -13.00  26.00   0.50   35.00    --  -48.45  19.00-120.00   78
  7  ω    -34.00  12.00   0.50   35.00    --  -48.45  37.00-180.00   92
  8  ω    -67.00 -20.00   0.50   35.00    --  -48.45 125.00 -60.00   94
  9  ω    108.00 178.00   0.50  100.00    --  111.50  45.00-180.00  140
 10  ω     45.00 102.00   0.50  100.00    --  111.50-125.00 -90.00  114
 11  ω     55.00 107.00   0.50  100.00    --  111.50-125.00   0.00  104
 12  ω     40.00  77.00   0.50  100.00    --  111.50 -61.00  90.00   74
 13  ω     91.00 124.00   0.50  100.00    --  111.50-144.00 -83.00   66
 14  ω     40.00  68.00   0.50  100.00    --  111.50 -61.00  30.00   56
 15  ω    128.00 174.00   0.50  100.00    --  111.50  45.00  90.00   92
 16  ω     40.00  76.00   0.50  100.00    --  111.50 -61.00  60.00   72
 17  ω     52.00  77.00   0.50  100.00    --  111.50-126.00  84.00   50
 18  ω    -77.00 -52.00   0.50  100.00    --  -90.00 126.00 161.00   50
 19  ω   -119.00 -54.00   0.50   50.00    --  -48.32 -57.00 -60.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0680075000
_diffrn_orient_matrix_UB_12      -0.0782322000
_diffrn_orient_matrix_UB_13      0.0147262000
_diffrn_orient_matrix_UB_21      -0.1032908000
_diffrn_orient_matrix_UB_22      -0.0533079000
_diffrn_orient_matrix_UB_23      0.0040242000
_diffrn_orient_matrix_UB_31      0.0080661000
_diffrn_orient_matrix_UB_32      -0.0190315000
_diffrn_orient_matrix_UB_33      -0.0713377000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3071
_reflns_number_total             4433
_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 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.00119(15)
_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   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.038
_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)+(0.0708P)²+1.9554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1500
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H5 of C5, H1A of C1, H8 of C8, H12 of C12, H13 of C13, H4 of C4, H20 of C20,
   H11 of C11, H9 of C9, H6 of C6, H21 of C21, H27 of C27, H29 of C29, H25 of
  C25, H28 of C28, H22 of C22, H24 of C24
 At 1.5 times of:
  H1 of C24
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32182(12) 0.63028(10) 0.25766(7) 0.0285(4) Uani 1 1 d D . . . .
N1 N 0.45570(14) 0.57108(12) 0.31784(8) 0.0250(4) Uani 1 1 d . . . . .
N2 N 0.62720(14) 0.60552(13) 0.30153(8) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.34416(17) 0.56185(15) 0.29784(10) 0.0259(5) Uani 1 1 d . . . . .
H1A H 0.296838 0.565850 0.335997 0.031 Uiso 1 1 calc R U . . .
C2 C 0.53609(17) 0.58205(15) 0.27460(10) 0.0255(5) Uani 1 1 d . . . . .
C3 C 0.52501(17) 0.56784(15) 0.20642(10) 0.0261(5) Uani 1 1 d . . . . .
C4 C 0.58769(17) 0.61885(16) 0.16790(11) 0.0294(5) Uani 1 1 d . . . . .
H4 H 0.620261 0.667494 0.185425 0.035 Uiso 1 1 calc R U . . .
C5 C 0.60380(18) 0.60029(16) 0.10425(10) 0.0305(5) Uani 1 1 d . . . . .
H5 H 0.642963 0.637560 0.077795 0.037 Uiso 1 1 calc R U . . .
C6 C 0.56203(17) 0.52707(16) 0.08036(10) 0.0290(5) Uani 1 1 d . . . . .
H6 H 0.579393 0.510859 0.038312 0.035 Uiso 1 1 calc R U . . .
C7 C 0.49439(18) 0.47572(16) 0.11663(10) 0.0282(5) Uani 1 1 d . . . . .
C8 C 0.45546(19) 0.39871(16) 0.09030(10) 0.0319(5) Uani 1 1 d . . . . .
H8 H 0.476619 0.382936 0.048756 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3895(2) 0.34841(16) 0.12339(11) 0.0338(5) Uani 1 1 d . . . . .
H9 H 0.370165 0.295156 0.106722 0.041 Uiso 1 1 calc R U . . .
C10 C 0.34801(19) 0.37427(16) 0.18357(10) 0.0306(5) Uani 1 1 d . . . . .
C11 C 0.2673(2) 0.32532(16) 0.21230(11) 0.0336(5) Uani 1 1 d . . . . .
H11 H 0.248287 0.272839 0.194170 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2160(2) 0.35201(16) 0.26573(11) 0.0332(5) Uani 1 1 d . . . . .
H12 H 0.161133 0.318812 0.284489 0.040 Uiso 1 1 calc R U . . .
C13 C 0.24519(18) 0.42867(16) 0.29237(10) 0.0302(5) Uani 1 1 d . . . . .
H13 H 0.208525 0.447787 0.329091 0.036 Uiso 1 1 calc R U . . .
C14 C 0.32624(17) 0.47780(15) 0.26680(9) 0.0265(5) Uani 1 1 d . . . . .
C15 C 0.38284(18) 0.45088(15) 0.21165(10) 0.0268(5) Uani 1 1 d . . . . .
C16 C 0.46618(17) 0.49927(15) 0.17965(10) 0.0259(5) Uani 1 1 d . . . . .
C17 C 0.60448(17) 0.61081(14) 0.36533(10) 0.0255(5) Uani 1 1 d . . . . .
C18 C 0.49859(17) 0.59022(15) 0.37705(10) 0.0260(5) Uani 1 1 d . . . . .
C19 C 0.45315(18) 0.58803(15) 0.43969(10) 0.0269(5) Uani 1 1 d . . . . .
C20 C 0.35277(18) 0.55489(16) 0.45635(11) 0.0296(5) Uani 1 1 d . . . . .
H20 H 0.308842 0.529938 0.424739 0.036 Uiso 1 1 calc R U . . .
C21 C 0.31677(19) 0.55807(16) 0.51834(11) 0.0320(5) Uani 1 1 d . . . . .
H21 H 0.248362 0.535372 0.528702 0.038 Uiso 1 1 calc R U . . .
C22 C 0.37881(19) 0.59368(16) 0.56514(10) 0.0318(5) Uani 1 1 d . . . . .
H22 H 0.351440 0.597674 0.607022 0.038 Uiso 1 1 calc R U . . .
C23 C 0.48134(19) 0.62392(16) 0.55164(10) 0.0303(5) Uani 1 1 d . . . . .
C24 C 0.5492(2) 0.65743(16) 0.60067(11) 0.0340(6) Uani 1 1 d . . . . .
H24 H 0.522257 0.661420 0.642640 0.041 Uiso 1 1 calc R U . . .
H1 H 0.2575(17) 0.620(2) 0.2399(12) 0.051 Uiso 1 1 d D U . . .
C25 C 0.6502(2) 0.68330(16) 0.58826(11) 0.0344(6) Uani 1 1 d . . . . .
H25 H 0.692100 0.706878 0.621402 0.041 Uiso 1 1 calc R U . . .
C26 C 0.69596(19) 0.67605(15) 0.52623(10) 0.0297(5) Uani 1 1 d . . . . .
C27 C 0.8034(2) 0.69648(16) 0.51422(11) 0.0333(6) Uani 1 1 d . . . . .
H27 H 0.846479 0.719178 0.547156 0.040 Uiso 1 1 calc R U . . .
C28 C 0.84748(19) 0.68396(16) 0.45483(11) 0.0320(5) Uani 1 1 d . . . . .
H28 H 0.921292 0.696152 0.447793 0.038 Uiso 1 1 calc R U . . .
C29 C 0.78540(18) 0.65402(15) 0.40586(10) 0.0288(5) Uani 1 1 d . . . . .
H29 H 0.816973 0.645219 0.365457 0.035 Uiso 1 1 calc R U . . .
C30 C 0.67665(18) 0.63647(15) 0.41493(10) 0.0269(5) Uani 1 1 d . . . . .
C31 C 0.63015(19) 0.64537(15) 0.47618(10) 0.0271(5) Uani 1 1 d . . . . .
C32 C 0.52098(18) 0.62055(15) 0.48853(10) 0.0274(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
O1 C1 1.410(3) . ?
O1 H1 0.899(18) . ?
N1 C1 1.457(3) . ?
N1 C2 1.365(3) . ?
N1 C18 1.394(3) . ?
N2 C2 1.322(3) . ?
N2 C17 1.379(3) . ?
C1 H1A 1.0000 . ?
C1 C14 1.508(3) . ?
C2 C3 1.464(3) . ?
C3 C4 1.390(3) . ?
C3 C16 1.432(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.402(3) . ?
C7 C8 1.432(3) . ?
C7 C16 1.427(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.343(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.433(3) . ?
C10 C11 1.409(3) . ?
C10 C15 1.425(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.365(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C14 C15 1.427(3) . ?
C15 C16 1.458(3) . ?
C17 C18 1.380(3) . ?
C17 C30 1.439(3) . ?
C18 C19 1.439(3) . ?
C19 C20 1.400(3) . ?
C19 C32 1.430(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.393(3) . ?
C23 C24 1.439(3) . ?
C23 C32 1.422(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.348(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.433(3) . ?
C26 C27 1.398(3) . ?
C26 C31 1.424(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.384(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.376(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.394(3) . ?
C30 C31 1.424(3) . ?
C31 C32 1.438(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 107(2) . . ?
C2 N1 C1 121.05(17) . . ?
C2 N1 C18 106.99(17) . . ?
C18 N1 C1 130.28(18) . . ?
C2 N2 C17 105.20(17) . . ?
O1 C1 N1 106.50(18) . . ?
O1 C1 H1A 108.7 . . ?
O1 C1 C14 113.36(17) . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 C14 110.87(18) . . ?
C14 C1 H1A 108.7 . . ?
N1 C2 C3 124.70(19) . . ?
N2 C2 N1 112.08(18) . . ?
N2 C2 C3 123.21(19) . . ?
C4 C3 C2 115.6(2) . . ?
C4 C3 C16 120.1(2) . . ?
C16 C3 C2 123.7(2) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.5(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 C16 120.3(2) . . ?
C16 C7 C8 120.3(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 C15 120.8(2) . . ?
C15 C10 C9 120.4(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.1(2) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C1 116.1(2) . . ?
C13 C14 C15 120.4(2) . . ?
C15 C14 C1 123.3(2) . . ?
C10 C15 C14 116.6(2) . . ?
C10 C15 C16 118.4(2) . . ?
C14 C15 C16 124.7(2) . . ?
C3 C16 C15 125.73(19) . . ?
C7 C16 C3 116.3(2) . . ?
C7 C16 C15 117.9(2) . . ?
N2 C17 C30 126.94(19) . . ?
C18 C17 N2 110.88(19) . . ?
C18 C17 C30 122.15(19) . . ?
N1 C18 C19 132.0(2) . . ?
C17 C18 N1 104.85(18) . . ?
C17 C18 C19 123.1(2) . . ?
C20 C19 C18 126.2(2) . . ?
C20 C19 C32 118.77(19) . . ?
C32 C19 C18 115.0(2) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.9(2) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 121.2(2) . . ?
C22 C23 C32 119.8(2) . . ?
C32 C23 C24 119.0(2) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.3(2) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 119.2 . . ?
C24 C25 C26 121.5(2) . . ?
C26 C25 H25 119.2 . . ?
C27 C26 C25 121.8(2) . . ?
C27 C26 C31 119.6(2) . . ?
C31 C26 C25 118.6(2) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.6(2) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.7(2) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C17 124.2(2) . . ?
C29 C30 C31 119.9(2) . . ?
C31 C30 C17 115.9(2) . . ?
C26 C31 C30 118.4(2) . . ?
C26 C31 C32 120.2(2) . . ?
C30 C31 C32 121.4(2) . . ?
C19 C32 C31 121.73(19) . . ?
C23 C32 C19 119.0(2) . . ?
C23 C32 C31 119.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N2 0.899(18) 1.856(18) 2.753(2) 175(3) 6_556 yes

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 C1 C14 C13 -115.4(2) . . . . ?
O1 C1 C14 C15 60.4(3) . . . . ?
N1 C1 C14 C13 124.8(2) . . . . ?
N1 C1 C14 C15 -59.3(3) . . . . ?
N1 C2 C3 C4 148.4(2) . . . . ?
N1 C2 C3 C16 -40.1(3) . . . . ?
N1 C18 C19 C20 8.2(4) . . . . ?
N1 C18 C19 C32 -174.2(2) . . . . ?
N2 C2 C3 C4 -33.2(3) . . . . ?
N2 C2 C3 C16 138.4(2) . . . . ?
N2 C17 C18 N1 0.4(3) . . . . ?
N2 C17 C18 C19 178.2(2) . . . . ?
N2 C17 C30 C29 -5.3(4) . . . . ?
N2 C17 C30 C31 173.4(2) . . . . ?
C1 N1 C2 N2 167.5(2) . . . . ?
C1 N1 C2 C3 -13.9(3) . . . . ?
C1 N1 C18 C17 -165.8(2) . . . . ?
C1 N1 C18 C19 16.8(4) . . . . ?
C1 C14 C15 C10 -172.7(2) . . . . ?
C1 C14 C15 C16 1.8(3) . . . . ?
C2 N1 C1 O1 -52.1(3) . . . . ?
C2 N1 C1 C14 71.6(3) . . . . ?
C2 N1 C18 C17 -0.8(2) . . . . ?
C2 N1 C18 C19 -178.2(2) . . . . ?
C2 N2 C17 C18 0.1(3) . . . . ?
C2 N2 C17 C30 -178.0(2) . . . . ?
C2 C3 C4 C5 165.4(2) . . . . ?
C2 C3 C16 C7 -157.5(2) . . . . ?
C2 C3 C16 C15 20.9(3) . . . . ?
C3 C4 C5 C6 -4.1(3) . . . . ?
C4 C3 C16 C7 13.7(3) . . . . ?
C4 C3 C16 C15 -167.9(2) . . . . ?
C4 C5 C6 C7 7.0(3) . . . . ?
C5 C6 C7 C8 -178.1(2) . . . . ?
C5 C6 C7 C16 0.7(3) . . . . ?
C6 C7 C8 C9 -179.2(2) . . . . ?
C6 C7 C16 C3 -10.9(3) . . . . ?
C6 C7 C16 C15 170.6(2) . . . . ?
C7 C8 C9 C10 6.0(4) . . . . ?
C8 C7 C16 C3 168.0(2) . . . . ?
C8 C7 C16 C15 -10.5(3) . . . . ?
C8 C9 C10 C11 170.9(2) . . . . ?
C8 C9 C10 C15 -5.1(4) . . . . ?
C9 C10 C11 C12 -172.2(2) . . . . ?
C9 C10 C15 C14 171.1(2) . . . . ?
C9 C10 C15 C16 -3.8(3) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C10 C15 C16 C3 -167.1(2) . . . . ?
C10 C15 C16 C7 11.2(3) . . . . ?
C11 C10 C15 C14 -4.7(3) . . . . ?
C11 C10 C15 C16 -179.6(2) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C12 C13 C14 C1 176.0(2) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C10 2.9(3) . . . . ?
C13 C14 C15 C16 177.4(2) . . . . ?
C14 C15 C16 C3 18.4(3) . . . . ?
C14 C15 C16 C7 -163.2(2) . . . . ?
C15 C10 C11 C12 3.7(4) . . . . ?
C16 C3 C4 C5 -6.5(3) . . . . ?
C16 C7 C8 C9 1.9(3) . . . . ?
C17 N2 C2 N1 -0.6(3) . . . . ?
C17 N2 C2 C3 -179.2(2) . . . . ?
C17 C18 C19 C20 -168.8(2) . . . . ?
C17 C18 C19 C32 8.8(3) . . . . ?
C17 C30 C31 C26 -175.8(2) . . . . ?
C17 C30 C31 C32 7.0(3) . . . . ?
C18 N1 C1 O1 111.0(2) . . . . ?
C18 N1 C1 C14 -125.2(2) . . . . ?
C18 N1 C2 N2 0.9(3) . . . . ?
C18 N1 C2 C3 179.5(2) . . . . ?
C18 C17 C30 C29 176.8(2) . . . . ?
C18 C17 C30 C31 -4.5(3) . . . . ?
C18 C19 C20 C21 -178.6(2) . . . . ?
C18 C19 C32 C23 177.6(2) . . . . ?
C18 C19 C32 C31 -6.0(3) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C19 C32 C23 -4.6(3) . . . . ?
C20 C19 C32 C31 171.8(2) . . . . ?
C20 C21 C22 C23 -2.9(4) . . . . ?
C21 C22 C23 C24 -176.8(2) . . . . ?
C21 C22 C23 C32 2.1(4) . . . . ?
C22 C23 C24 C25 177.0(2) . . . . ?
C22 C23 C32 C19 1.7(4) . . . . ?
C22 C23 C32 C31 -174.8(2) . . . . ?
C23 C24 C25 C26 -2.1(4) . . . . ?
C24 C23 C32 C19 -179.4(2) . . . . ?
C24 C23 C32 C31 4.2(3) . . . . ?
C24 C25 C26 C27 -174.8(2) . . . . ?
C24 C25 C26 C31 3.8(4) . . . . ?
C25 C26 C27 C28 175.9(2) . . . . ?
C25 C26 C31 C30 -178.6(2) . . . . ?
C25 C26 C31 C32 -1.4(3) . . . . ?
C26 C27 C28 C29 2.4(4) . . . . ?
C26 C31 C32 C19 -178.8(2) . . . . ?
C26 C31 C32 C23 -2.5(3) . . . . ?
C27 C26 C31 C30 0.0(3) . . . . ?
C27 C26 C31 C32 177.2(2) . . . . ?
C27 C28 C29 C30 0.6(4) . . . . ?
C28 C29 C30 C17 175.3(2) . . . . ?
C28 C29 C30 C31 -3.3(4) . . . . ?
C29 C30 C31 C26 2.9(3) . . . . ?
C29 C30 C31 C32 -174.2(2) . . . . ?
C30 C17 C18 N1 178.6(2) . . . . ?
C30 C17 C18 C19 -3.6(4) . . . . ?
C30 C31 C32 C19 -1.8(4) . . . . ?
C30 C31 C32 C23 174.6(2) . . . . ?
C31 C26 C27 C28 -2.6(4) . . . . ?
C32 C19 C20 C21 3.9(4) . . . . ?
C32 C23 C24 C25 -1.9(4) . . . . ?

_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 2.098
_oxdiff_exptl_absorpt_empirical_full_min 0.385
####################################################################### 
# 
# 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_lb-01-007
_audit_block_doi                 10.5517/ccdc.csd.cc2mkyhn
_database_code_depnum_ccdc_archive 'CCDC 2430322'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2026-01-26 downloaded from the CCDC.
;
_audit_creation_date             2024-05-15
_audit_creation_method           
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H B F15 O, C32 H17 N2 O'
_chemical_formula_sum            'C50 H18 B F15 N2 O2'
_chemical_formula_weight         974.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         C50H17BF16N2O
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'
B B 0.0090 0.0039 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.61620(10)
_cell_length_b                   7.91840(10)
_cell_length_c                   30.8317(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.4280(10)
_cell_angle_gamma                90
_cell_volume                     3780.51(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18671
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.1950
_cell_measurement_theta_min      2.8400
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.120a (Rigaku Oxford Diffraction, 2024)
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    1.712
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 -1 0.0201
-9 0 11 0.0194
3 5 -9 0.0369
-10 0 9 0.0183
8 -3 -3 0.0225
6 3 9 0.0267
-8 1 -8 0.0172
-1 -4 -12 0.0346
-2 2 -18 0.0192
0 5 -5 0.0317
0 1 19 0.0187
5 -4 9 0.0267

_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9995 -0.9995 -0.9998 0.0955 -0.0297 0.2593
-8.9728 -0.3616 11.4227 -0.9289 0.2228 -0.2960
2.5812 4.5324 -8.5227 0.7073 -0.0935 -0.7007
-9.5381 0.0902 9.1562 -0.9024 0.1185 -0.4144
7.7327 -3.3141 -3.1237 0.4022 -0.0523 0.9141
5.9272 3.1889 8.8450 0.5965 0.7771 -0.2007
-8.4297 1.1935 -7.8675 -0.4583 -0.5980 -0.6576
-0.5996 -4.0584 -11.9649 -0.1898 -0.7892 0.5841
-2.0502 1.6537 -17.8326 0.2474 -0.8338 -0.4935
-0.2466 4.9517 -5.2299 0.4625 -0.0115 -0.8865
0.0677 1.3774 19.1010 -0.1813 0.9774 -0.1085
5.3446 -3.5347 8.5502 0.0101 0.4107 0.9117

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            49661
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.706
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -32.00   0.50   18.01    --  -47.13 -38.00 -45.00  178
  2  ω    -35.00  27.00   0.50   18.01    --  -47.13  38.00 108.00  124
  3  ω    -26.00  49.00   0.50   18.01    --   47.13 -38.00 -45.00  150
  4  ω     33.00 121.00   0.50   18.01    --   47.13  38.00 108.00  176
  5  ω   -165.00 -77.00   0.50   72.06    --  -91.75 -38.00 -45.00  176
  6  ω     99.00 178.00   0.50   72.06    --  113.25  38.00 108.00  158
  7  ω    -16.00  28.00   0.50   18.01    --  -47.13  19.00 -30.00   88
  8  ω    -16.00  28.00   0.50   18.01    --  -47.13  19.00  90.00   88
  9  ω    -16.00  28.00   0.50   18.01    --  -47.13  19.00-120.00   88
 10  ω    -85.00 -22.00   0.50   72.06    --  -91.75 125.00 150.00  126
 11  ω    -65.00 -19.00   0.50   72.06    --  -91.75  61.00-150.00   92
 12  ω     41.00  79.00   0.50   72.06    --  113.25 -61.00  30.00   76
 13  ω     41.00  79.00   0.50   72.06    --  113.25 -61.00-180.00   76
 14  ω     41.00  79.00   0.50   72.06    --  113.25 -61.00 -30.00   76
 15  ω     41.00  79.00   0.50   72.06    --  113.25 -61.00   0.00   76
 16  ω     41.00 137.00   0.50   72.06    --  113.25 -77.00-120.00  192
 17  ω     99.00 178.00   0.50   72.06    --  113.25  30.00-120.00  158
 18  ω     41.00  79.00   0.50   72.06    --  113.25 -61.00 -90.00   76
 19  ω     41.00  79.00   0.50   72.06    --  113.25 -61.00  90.00   76
 20  ω     99.00 178.00   0.50   72.06    --  113.25  45.00-180.00  158
 21  ω     96.00 178.00   0.50   72.06    --  113.25  61.00-150.00  164
 22  ω     41.00 137.00   0.50   72.06    --  113.25 -77.00-120.00  192
 23  ω     96.00 178.00   0.50   72.06    --  113.25  61.00 120.00  164
 24  ω     95.00 178.00   0.50   72.06    --  113.25 125.00  30.00  166
 25  ω     95.00 178.00   0.50   72.06    --  113.25 125.00  30.00  166
 26  ω     41.00 106.00   0.50   72.06    --  113.25 -94.00  60.00  130
 27  ω     99.00 178.00   0.50   72.06    --  113.25  45.00 -30.00  158
 28  ω     41.00 106.00   0.50   72.06    --  113.25 -94.00-150.00  130
 29  ω     41.00 106.00   0.50   72.06    --  113.25 -94.00  90.00  130
 30  ω     41.00  79.00   0.50   72.06    --  113.25 -61.00 120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0803870000
_diffrn_orient_matrix_UB_12      0.0809208000
_diffrn_orient_matrix_UB_13      -0.0156094000
_diffrn_orient_matrix_UB_21      0.0336261000
_diffrn_orient_matrix_UB_22      0.0494986000
_diffrn_orient_matrix_UB_23      0.0474836000
_diffrn_orient_matrix_UB_31      0.0479823000
_diffrn_orient_matrix_UB_32      -0.1698859000
_diffrn_orient_matrix_UB_33      0.0064025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6676
_reflns_number_total             8087
_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 1.171.43.120a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.120a (release 16-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         8087
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0403
_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)+(0.0525P)²+2.7286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1110
_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:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens   mixed
_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 0.43951(6) 0.85015(13) 0.28336(3) 0.0271(2) Uani 1 1 d . . . . .
F2 F 0.57773(6) 0.65311(15) 0.28591(4) 0.0320(2) Uani 1 1 d . . . . .
F3 F 0.56622(7) 0.31563(15) 0.30416(4) 0.0320(2) Uani 1 1 d . . . . .
F4 F 0.41113(7) 0.18228(14) 0.31536(4) 0.0325(2) Uani 1 1 d . . . . .
F5 F 0.27038(6) 0.37201(13) 0.30971(4) 0.0289(2) Uani 1 1 d . . . . .
F6 F 0.23640(8) 0.52577(15) 0.21904(4) 0.0371(3) Uani 1 1 d . . . . .
F7 F 0.22966(9) 0.60252(17) 0.13388(4) 0.0432(3) Uani 1 1 d . . . . .
F8 F 0.22486(8) 0.92870(17) 0.10723(3) 0.0382(3) Uani 1 1 d . . . . .
F9 F 0.23828(8) 1.18013(15) 0.16792(4) 0.0358(3) Uani 1 1 d . . . . .
F10 F 0.25133(7) 1.11041(14) 0.25229(3) 0.0313(2) Uani 1 1 d . . . . .
F11 F 0.07614(7) 0.74852(15) 0.25027(4) 0.0334(2) Uani 1 1 d . . . . .
F12 F -0.05424(7) 0.61587(17) 0.28507(4) 0.0424(3) Uani 1 1 d . . . . .
F13 F -0.02933(8) 0.46920(16) 0.36588(4) 0.0427(3) Uani 1 1 d . . . . .
F14 F 0.13149(8) 0.47681(16) 0.41303(4) 0.0390(3) Uani 1 1 d . . . . .
F15 F 0.26436(7) 0.60673(14) 0.37843(3) 0.0301(2) Uani 1 1 d . . . . .
O2 O 0.29217(8) 0.90665(17) 0.32160(4) 0.0233(2) Uani 1 1 d . . . . .
H2A H 0.3084(18) 0.983(4) 0.3104(9) 0.045(8) Uiso 1 1 d . . . . .
C33 C 0.34675(11) 0.6233(2) 0.29677(5) 0.0222(3) Uani 1 1 d . . . . .
C34 C 0.42835(11) 0.6841(2) 0.29104(5) 0.0239(3) Uani 1 1 d . . . . .
C35 C 0.50169(11) 0.5851(2) 0.29257(6) 0.0258(4) Uani 1 1 d . . . . .
C36 C 0.49609(11) 0.4155(2) 0.30090(6) 0.0258(4) Uani 1 1 d . . . . .
C37 C 0.41701(12) 0.3479(2) 0.30669(6) 0.0258(4) Uani 1 1 d . . . . .
C38 C 0.34501(11) 0.4509(2) 0.30409(6) 0.0244(3) Uani 1 1 d . . . . .
C39 C 0.24724(10) 0.8129(2) 0.24085(5) 0.0229(3) Uani 1 1 d . . . . .
C40 C 0.23940(11) 0.6908(2) 0.20807(6) 0.0266(4) Uani 1 1 d . . . . .
C41 C 0.23348(12) 0.7265(3) 0.16388(6) 0.0300(4) Uani 1 1 d . . . . .
C42 C 0.23228(11) 0.8916(3) 0.15016(6) 0.0293(4) Uani 1 1 d . . . . .
C43 C 0.23833(11) 1.0182(2) 0.18077(6) 0.0272(4) Uani 1 1 d . . . . .
C44 C 0.24544(11) 0.9768(2) 0.22478(5) 0.0236(3) Uani 1 1 d . . . . .
C45 C 0.17886(11) 0.6804(2) 0.31184(6) 0.0239(3) Uani 1 1 d . . . . .
C46 C 0.09493(11) 0.6798(2) 0.29050(6) 0.0267(4) Uani 1 1 d . . . . .
C47 C 0.02515(11) 0.6110(3) 0.30795(7) 0.0312(4) Uani 1 1 d . . . . .
C48 C 0.03698(12) 0.5405(3) 0.34886(7) 0.0330(4) Uani 1 1 d . . . . .
C49 C 0.11827(13) 0.5430(2) 0.37245(6) 0.0301(4) Uani 1 1 d . . . . .
C50 C 0.18589(11) 0.6120(2) 0.35371(6) 0.0261(4) Uani 1 1 d . . . . .
B1 B 0.26484(12) 0.7585(3) 0.29299(6) 0.0224(4) Uani 1 1 d . . . . .
O1 O 0.22692(9) 1.0319(2) 0.53206(4) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.26000(10) 0.9225(2) 0.46799(5) 0.0276(3) Uani 1 1 d . . . . .
N2 N 0.31080(10) 0.9475(2) 0.40547(5) 0.0261(3) Uani 1 1 d . . . . .
H2 H 0.3068(19) 0.937(4) 0.3716(10) 0.062(8) Uiso 1 1 d . . . . .
C1 C 0.34801(11) 0.8776(2) 0.47573(6) 0.0274(4) Uani 1 1 d . . . . .
C2 C 0.37770(11) 0.8927(2) 0.43584(6) 0.0265(4) Uani 1 1 d . . . . .
C3 C 0.46355(12) 0.8494(2) 0.42834(6) 0.0280(4) Uani 1 1 d . . . . .
C4 C 0.49476(12) 0.8726(3) 0.38867(6) 0.0307(4) Uani 1 1 d . . . . .
H4 H 0.458845 0.921327 0.364693 0.037 Uiso 1 1 calc R U . . .
C5 C 0.57929(12) 0.8242(3) 0.38401(7) 0.0356(4) Uani 1 1 d . . . . .
H5 H 0.600977 0.841316 0.356942 0.043 Uiso 1 1 calc R U . . .
C6 C 0.63090(12) 0.7519(3) 0.41846(7) 0.0361(4) Uani 1 1 d . . . . .
H6 H 0.687546 0.716678 0.414538 0.043 Uiso 1 1 calc R U . . .
C7 C 0.60212(12) 0.7288(3) 0.45932(7) 0.0336(4) Uani 1 1 d . . . . .
C8 C 0.65550(13) 0.6542(3) 0.49565(7) 0.0387(5) Uani 1 1 d . . . . .
H8 H 0.712523 0.619846 0.492226 0.046 Uiso 1 1 calc R U . . .
C9 C 0.62638(14) 0.6319(3) 0.53467(7) 0.0401(5) Uani 1 1 d . . . . .
H9 H 0.663497 0.583108 0.558194 0.048 Uiso 1 1 calc R U . . .
C10 C 0.54026(13) 0.6806(3) 0.54124(6) 0.0350(4) Uani 1 1 d . . . . .
C11 C 0.50919(15) 0.6516(3) 0.58111(7) 0.0413(5) Uani 1 1 d . . . . .
H11 H 0.545444 0.598996 0.604358 0.050 Uiso 1 1 calc R U . . .
C12 C 0.42658(15) 0.6984(3) 0.58706(7) 0.0429(5) Uani 1 1 d . . . . .
H12 H 0.406514 0.677031 0.614346 0.051 Uiso 1 1 calc R U . . .
C13 C 0.37225(14) 0.7761(3) 0.55387(6) 0.0371(4) Uani 1 1 d . . . . .
H13 H 0.315756 0.808876 0.558746 0.045 Uiso 1 1 calc R U . . .
C14 C 0.40006(12) 0.8066(3) 0.51329(6) 0.0305(4) Uani 1 1 d . . . . .
C15 C 0.48504(12) 0.7575(2) 0.50622(6) 0.0302(4) Uani 1 1 d . . . . .
C16 C 0.51656(12) 0.7800(3) 0.46476(6) 0.0298(4) Uani 1 1 d . . . . .
C17 C 0.24008(11) 0.9640(2) 0.42520(6) 0.0262(4) Uani 1 1 d . . . . .
C18 C 0.20116(12) 0.9549(3) 0.49974(6) 0.0295(4) Uani 1 1 d . . . . .
C19 C 0.11587(12) 0.8719(2) 0.49156(6) 0.0293(4) Uani 1 1 d . . . . .
C20 C 0.09140(13) 0.8027(3) 0.52966(7) 0.0351(4) Uani 1 1 d . . . . .
H20 H 0.128449 0.814206 0.556467 0.042 Uiso 1 1 calc R U . . .
C21 C 0.01351(14) 0.7170(3) 0.52899(8) 0.0401(5) Uani 1 1 d . . . . .
H21 H -0.001497 0.665418 0.554792 0.048 Uiso 1 1 calc R U . . .
C22 C -0.04114(14) 0.7080(3) 0.49067(8) 0.0405(5) Uani 1 1 d . . . . .
H22 H -0.094334 0.649321 0.490164 0.049 Uiso 1 1 calc R U . . .
C23 C -0.02065(13) 0.7834(3) 0.45185(7) 0.0352(4) Uani 1 1 d . . . . .
C24 C -0.08482(13) 0.7874(3) 0.41442(8) 0.0418(5) Uani 1 1 d . . . . .
H24 H -0.136787 0.725203 0.414649 0.050 Uiso 1 1 calc R U . . .
C25 C -0.07268(13) 0.8776(3) 0.37898(8) 0.0412(5) Uani 1 1 d . . . . .
H25 H -0.117531 0.883796 0.355078 0.049 Uiso 1 1 calc R U . . .
C26 C 0.00673(13) 0.9648(3) 0.37657(7) 0.0345(4) Uani 1 1 d . . . . .
C27 C 0.01556(14) 1.0605(3) 0.33891(7) 0.0383(5) Uani 1 1 d . . . . .
H27 H -0.032288 1.070428 0.316657 0.046 Uiso 1 1 calc R U . . .
C28 C 0.09140(14) 1.1395(3) 0.33360(7) 0.0373(5) Uani 1 1 d . . . . .
H28 H 0.095435 1.209903 0.309003 0.045 Uiso 1 1 calc R U . . .
C29 C 0.16249(13) 1.1142(3) 0.36508(6) 0.0320(4) Uani 1 1 d . . . . .
H29 H 0.215966 1.165735 0.361288 0.038 Uiso 1 1 calc R U . . .
C30 C 0.15725(12) 1.0155(2) 0.40195(6) 0.0275(4) Uani 1 1 d . . . . .
C31 C 0.07658(12) 0.9475(2) 0.41083(6) 0.0288(4) Uani 1 1 d . . . . .
C32 C 0.06052(12) 0.8634(2) 0.45108(6) 0.0295(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C34 1.352(2) . ?
F2 C35 1.344(2) . ?
F3 C36 1.344(2) . ?
F4 C37 1.344(2) . ?
F5 C38 1.3528(19) . ?
F6 C40 1.352(2) . ?
F7 C41 1.345(2) . ?
F8 C42 1.346(2) . ?
F9 C43 1.342(2) . ?
F10 C44 1.351(2) . ?
F11 C46 1.352(2) . ?
F12 C47 1.345(2) . ?
F13 C48 1.344(2) . ?
F14 C49 1.347(2) . ?
F15 C50 1.357(2) . ?
O2 H2A 0.76(3) . ?
O2 B1 1.496(2) . ?
C33 C34 1.394(2) . ?
C33 C38 1.385(3) . ?
C33 B1 1.661(3) . ?
C34 C35 1.384(2) . ?
C35 C36 1.372(3) . ?
C36 C37 1.379(3) . ?
C37 C38 1.383(3) . ?
C39 C40 1.392(3) . ?
C39 C44 1.388(3) . ?
C39 B1 1.653(3) . ?
C40 C41 1.383(3) . ?
C41 C42 1.373(3) . ?
C42 C43 1.372(3) . ?
C43 C44 1.386(2) . ?
C45 C46 1.388(2) . ?
C45 C50 1.391(2) . ?
C45 B1 1.651(2) . ?
C46 C47 1.388(2) . ?
C47 C48 1.369(3) . ?
C48 C49 1.379(3) . ?
C49 C50 1.380(2) . ?
O1 C18 1.193(2) . ?
N1 C1 1.410(2) . ?
N1 C17 1.356(2) . ?
N1 C18 1.449(2) . ?
N2 H2 1.04(3) . ?
N2 C2 1.380(2) . ?
N2 C17 1.334(2) . ?
C1 C2 1.375(2) . ?
C1 C14 1.440(3) . ?
C2 C3 1.431(3) . ?
C3 C4 1.386(3) . ?
C3 C16 1.417(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.403(3) . ?
C7 C8 1.434(3) . ?
C7 C16 1.427(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.351(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.438(3) . ?
C10 C11 1.398(3) . ?
C10 C15 1.429(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(3) . ?
C14 C15 1.426(3) . ?
C15 C16 1.439(3) . ?
C17 C30 1.454(3) . ?
C18 C19 1.477(3) . ?
C19 C20 1.394(3) . ?
C19 C32 1.425(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.367(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.411(3) . ?
C23 C24 1.428(3) . ?
C23 C32 1.420(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.340(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.430(3) . ?
C26 C27 1.408(3) . ?
C26 C31 1.424(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.368(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.391(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.391(3) . ?
C30 C31 1.429(3) . ?
C31 C32 1.458(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O2 H2A 116(2) . . ?
C34 C33 B1 118.49(15) . . ?
C38 C33 C34 113.47(16) . . ?
C38 C33 B1 128.02(15) . . ?
F1 C34 C33 119.90(15) . . ?
F1 C34 C35 115.61(15) . . ?
C35 C34 C33 124.49(17) . . ?
F2 C35 C34 120.78(17) . . ?
F2 C35 C36 119.99(16) . . ?
C36 C35 C34 119.23(16) . . ?
F3 C36 C35 121.25(16) . . ?
F3 C36 C37 119.78(17) . . ?
C35 C36 C37 118.96(16) . . ?
F4 C37 C36 119.36(16) . . ?
F4 C37 C38 120.72(16) . . ?
C36 C37 C38 119.92(17) . . ?
F5 C38 C33 120.75(15) . . ?
F5 C38 C37 115.34(16) . . ?
C37 C38 C33 123.91(16) . . ?
C40 C39 B1 120.88(16) . . ?
C44 C39 C40 113.23(15) . . ?
C44 C39 B1 125.71(15) . . ?
F6 C40 C39 119.48(16) . . ?
F6 C40 C41 116.36(16) . . ?
C41 C40 C39 124.15(18) . . ?
F7 C41 C40 121.29(18) . . ?
F7 C41 C42 119.05(16) . . ?
C42 C41 C40 119.65(17) . . ?
F8 C42 C41 120.43(17) . . ?
F8 C42 C43 120.44(18) . . ?
C43 C42 C41 119.12(16) . . ?
F9 C43 C42 119.84(16) . . ?
F9 C43 C44 120.77(17) . . ?
C42 C43 C44 119.39(18) . . ?
F10 C44 C39 120.75(15) . . ?
F10 C44 C43 114.82(16) . . ?
C43 C44 C39 124.42(16) . . ?
C46 C45 C50 113.25(16) . . ?
C46 C45 B1 126.55(16) . . ?
C50 C45 B1 120.16(15) . . ?
F11 C46 C45 120.87(15) . . ?
F11 C46 C47 115.20(16) . . ?
C47 C46 C45 123.93(17) . . ?
F12 C47 C46 120.12(18) . . ?
F12 C47 C48 120.01(16) . . ?
C48 C47 C46 119.86(17) . . ?
F13 C48 C47 120.77(18) . . ?
F13 C48 C49 120.19(19) . . ?
C47 C48 C49 119.04(16) . . ?
F14 C49 C48 120.29(16) . . ?
F14 C49 C50 120.59(18) . . ?
C48 C49 C50 119.12(18) . . ?
F15 C50 C45 119.35(15) . . ?
F15 C50 C49 115.90(16) . . ?
C49 C50 C45 124.73(17) . . ?
O2 B1 C33 107.79(14) . . ?
O2 B1 C39 111.61(14) . . ?
O2 B1 C45 105.61(13) . . ?
C39 B1 C33 105.42(13) . . ?
C45 B1 C33 112.83(14) . . ?
C45 B1 C39 113.55(14) . . ?
C1 N1 C18 128.29(15) . . ?
C17 N1 C1 108.77(14) . . ?
C17 N1 C18 121.90(16) . . ?
C2 N2 H2 126.6(17) . . ?
C17 N2 H2 121.3(16) . . ?
C17 N2 C2 108.66(15) . . ?
N1 C1 C14 132.15(16) . . ?
C2 C1 N1 105.11(15) . . ?
C2 C1 C14 122.19(17) . . ?
N2 C2 C3 127.50(16) . . ?
C1 C2 N2 108.74(16) . . ?
C1 C2 C3 123.71(17) . . ?
C4 C3 C2 123.65(17) . . ?
C4 C3 C16 120.98(17) . . ?
C16 C3 C2 115.37(16) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.86(18) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.13(18) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.67(18) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 122.26(19) . . ?
C6 C7 C16 118.80(18) . . ?
C16 C7 C8 118.94(18) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.38(19) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.24(19) . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 121.14(19) . . ?
C11 C10 C15 119.39(19) . . ?
C15 C10 C9 119.46(19) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.71(19) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C1 125.37(18) . . ?
C13 C14 C15 119.53(18) . . ?
C15 C14 C1 115.02(16) . . ?
C10 C15 C16 118.81(18) . . ?
C14 C15 C10 118.90(17) . . ?
C14 C15 C16 122.28(17) . . ?
C3 C16 C7 118.51(17) . . ?
C3 C16 C15 121.33(17) . . ?
C7 C16 C15 120.15(18) . . ?
N1 C17 C30 128.70(16) . . ?
N2 C17 N1 108.70(16) . . ?
N2 C17 C30 122.59(16) . . ?
O1 C18 N1 118.68(17) . . ?
O1 C18 C19 124.69(17) . . ?
N1 C18 C19 116.25(16) . . ?
C20 C19 C18 111.76(17) . . ?
C20 C19 C32 121.22(18) . . ?
C32 C19 C18 127.00(17) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.0(2) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.76(19) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C24 118.85(19) . . ?
C22 C23 C32 120.3(2) . . ?
C32 C23 C24 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(2) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C27 C26 C25 118.74(19) . . ?
C27 C26 C31 121.10(19) . . ?
C31 C26 C25 120.1(2) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.55(19) . . ?
C28 C27 H27 119.2 . . ?
C27 C28 H28 120.8 . . ?
C27 C28 C29 118.4(2) . . ?
C29 C28 H28 120.8 . . ?
C28 C29 H29 119.2 . . ?
C30 C29 C28 121.66(19) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 C17 114.72(17) . . ?
C29 C30 C31 121.01(17) . . ?
C31 C30 C17 123.36(17) . . ?
C26 C31 C30 115.56(18) . . ?
C26 C31 C32 118.42(17) . . ?
C30 C31 C32 126.02(17) . . ?
C19 C32 C31 124.91(17) . . ?
C23 C32 C19 116.61(18) . . ?
C23 C32 C31 118.04(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A F4 0.76(3) 2.24(3) 2.8886(17) 144(3) 1_565 yes
O2 H2A F10 0.76(3) 2.15(3) 2.6877(17) 129(3) . yes
N2 H2 O2 1.04(3) 1.55(3) 2.5849(19) 174(3) . yes

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 C34 C35 F2 -1.2(2) . . . . ?
F1 C34 C35 C36 179.00(15) . . . . ?
F2 C35 C36 F3 2.5(3) . . . . ?
F2 C35 C36 C37 -178.60(15) . . . . ?
F3 C36 C37 F4 -0.3(3) . . . . ?
F3 C36 C37 C38 178.90(15) . . . . ?
F4 C37 C38 F5 -1.6(2) . . . . ?
F4 C37 C38 C33 177.70(16) . . . . ?
F6 C40 C41 F7 -3.4(3) . . . . ?
F6 C40 C41 C42 177.18(16) . . . . ?
F7 C41 C42 F8 1.9(3) . . . . ?
F7 C41 C42 C43 -178.41(16) . . . . ?
F8 C42 C43 F9 -1.1(3) . . . . ?
F8 C42 C43 C44 179.65(15) . . . . ?
F9 C43 C44 F10 0.5(2) . . . . ?
F9 C43 C44 C39 -179.04(16) . . . . ?
F11 C46 C47 F12 -0.1(3) . . . . ?
F11 C46 C47 C48 -178.97(17) . . . . ?
F12 C47 C48 F13 2.9(3) . . . . ?
F12 C47 C48 C49 -177.41(18) . . . . ?
F13 C48 C49 F14 -1.3(3) . . . . ?
F13 C48 C49 C50 177.89(17) . . . . ?
F14 C49 C50 F15 0.5(3) . . . . ?
F14 C49 C50 C45 178.86(17) . . . . ?
C33 C34 C35 F2 178.77(15) . . . . ?
C33 C34 C35 C36 -1.1(3) . . . . ?
C34 C33 C38 F5 -179.12(15) . . . . ?
C34 C33 C38 C37 1.6(3) . . . . ?
C34 C33 B1 O2 -50.07(19) . . . . ?
C34 C33 B1 C39 69.26(19) . . . . ?
C34 C33 B1 C45 -166.28(15) . . . . ?
C34 C35 C36 F3 -177.71(15) . . . . ?
C34 C35 C36 C37 1.2(3) . . . . ?
C35 C36 C37 F4 -179.23(16) . . . . ?
C35 C36 C37 C38 -0.1(3) . . . . ?
C36 C37 C38 F5 179.22(15) . . . . ?
C36 C37 C38 C33 -1.5(3) . . . . ?
C38 C33 C34 F1 179.61(15) . . . . ?
C38 C33 C34 C35 -0.3(3) . . . . ?
C38 C33 B1 O2 131.68(18) . . . . ?
C38 C33 B1 C39 -109.00(19) . . . . ?
C38 C33 B1 C45 15.5(2) . . . . ?
C39 C40 C41 F7 177.17(16) . . . . ?
C39 C40 C41 C42 -2.2(3) . . . . ?
C40 C39 C44 F10 179.25(15) . . . . ?
C40 C39 C44 C43 -1.2(2) . . . . ?
C40 C39 B1 O2 166.16(15) . . . . ?
C40 C39 B1 C33 49.4(2) . . . . ?
C40 C39 B1 C45 -74.6(2) . . . . ?
C40 C41 C42 F8 -178.70(16) . . . . ?
C40 C41 C42 C43 1.0(3) . . . . ?
C41 C42 C43 F9 179.21(16) . . . . ?
C41 C42 C43 C44 0.0(3) . . . . ?
C42 C43 C44 F10 179.76(15) . . . . ?
C42 C43 C44 C39 0.2(3) . . . . ?
C44 C39 C40 F6 -177.15(15) . . . . ?
C44 C39 C40 C41 2.2(3) . . . . ?
C44 C39 B1 O2 -8.6(2) . . . . ?
C44 C39 B1 C33 -125.33(17) . . . . ?
C44 C39 B1 C45 110.67(18) . . . . ?
C45 C46 C47 F12 179.91(17) . . . . ?
C45 C46 C47 C48 1.0(3) . . . . ?
C46 C45 C50 F15 -179.20(15) . . . . ?
C46 C45 C50 C49 2.5(3) . . . . ?
C46 C45 B1 O2 112.96(19) . . . . ?
C46 C45 B1 C33 -129.53(18) . . . . ?
C46 C45 B1 C39 -9.6(3) . . . . ?
C46 C47 C48 F13 -178.21(17) . . . . ?
C46 C47 C48 C49 1.5(3) . . . . ?
C47 C48 C49 F14 179.01(17) . . . . ?
C47 C48 C49 C50 -1.8(3) . . . . ?
C48 C49 C50 F15 -178.61(16) . . . . ?
C48 C49 C50 C45 -0.3(3) . . . . ?
C50 C45 C46 F11 177.08(16) . . . . ?
C50 C45 C46 C47 -2.9(3) . . . . ?
C50 C45 B1 O2 -64.5(2) . . . . ?
C50 C45 B1 C33 53.0(2) . . . . ?
C50 C45 B1 C39 172.93(16) . . . . ?
B1 C33 C34 F1 1.1(2) . . . . ?
B1 C33 C34 C35 -178.83(16) . . . . ?
B1 C33 C38 F5 -0.8(3) . . . . ?
B1 C33 C38 C37 179.91(16) . . . . ?
B1 C39 C40 F6 7.5(2) . . . . ?
B1 C39 C40 C41 -173.13(16) . . . . ?
B1 C39 C44 F10 -5.7(2) . . . . ?
B1 C39 C44 C43 173.87(16) . . . . ?
B1 C45 C46 F11 -0.5(3) . . . . ?
B1 C45 C46 C47 179.54(17) . . . . ?
B1 C45 C50 F15 -1.4(2) . . . . ?
B1 C45 C50 C49 -179.70(17) . . . . ?
O1 C18 C19 C20 -36.5(3) . . . . ?
O1 C18 C19 C32 141.5(2) . . . . ?
N1 C1 C2 N2 1.1(2) . . . . ?
N1 C1 C2 C3 -176.31(17) . . . . ?
N1 C1 C14 C13 -4.9(4) . . . . ?
N1 C1 C14 C15 171.83(19) . . . . ?
N1 C17 C30 C29 154.42(19) . . . . ?
N1 C17 C30 C31 -36.5(3) . . . . ?
N1 C18 C19 C20 136.31(18) . . . . ?
N1 C18 C19 C32 -45.7(3) . . . . ?
N2 C2 C3 C4 6.5(3) . . . . ?
N2 C2 C3 C16 -173.72(18) . . . . ?
N2 C17 C30 C29 -26.8(3) . . . . ?
N2 C17 C30 C31 142.28(19) . . . . ?
C1 N1 C17 N2 0.0(2) . . . . ?
C1 N1 C17 C30 178.90(18) . . . . ?
C1 N1 C18 O1 40.2(3) . . . . ?
C1 N1 C18 C19 -133.0(2) . . . . ?
C1 C2 C3 C4 -176.62(19) . . . . ?
C1 C2 C3 C16 3.2(3) . . . . ?
C1 C14 C15 C10 -177.90(18) . . . . ?
C1 C14 C15 C16 0.9(3) . . . . ?
C2 N2 C17 N1 0.7(2) . . . . ?
C2 N2 C17 C30 -178.29(17) . . . . ?
C2 C1 C14 C13 -175.1(2) . . . . ?
C2 C1 C14 C15 1.6(3) . . . . ?
C2 C3 C4 C5 -178.98(19) . . . . ?
C2 C3 C16 C7 178.01(18) . . . . ?
C2 C3 C16 C15 -0.6(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C3 C16 C7 -2.2(3) . . . . ?
C4 C3 C16 C15 179.16(19) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
C5 C6 C7 C16 0.8(3) . . . . ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C6 C7 C16 C3 1.2(3) . . . . ?
C6 C7 C16 C15 179.83(19) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C7 C16 C3 -178.36(19) . . . . ?
C8 C7 C16 C15 0.3(3) . . . . ?
C8 C9 C10 C11 177.6(2) . . . . ?
C8 C9 C10 C15 -1.4(3) . . . . ?
C9 C10 C11 C12 -179.9(2) . . . . ?
C9 C10 C15 C14 -179.46(19) . . . . ?
C9 C10 C15 C16 1.7(3) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C10 C15 C16 C3 177.47(18) . . . . ?
C10 C15 C16 C7 -1.2(3) . . . . ?
C11 C10 C15 C14 1.5(3) . . . . ?
C11 C10 C15 C16 -177.3(2) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C1 176.4(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 -1.0(3) . . . . ?
C13 C14 C15 C16 177.81(19) . . . . ?
C14 C1 C2 N2 173.62(17) . . . . ?
C14 C1 C2 C3 -3.8(3) . . . . ?
C14 C15 C16 C3 -1.3(3) . . . . ?
C14 C15 C16 C7 -179.96(19) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
C16 C3 C4 C5 1.2(3) . . . . ?
C16 C7 C8 C9 0.0(3) . . . . ?
C17 N1 C1 C2 -0.7(2) . . . . ?
C17 N1 C1 C14 -172.2(2) . . . . ?
C17 N1 C18 O1 -126.8(2) . . . . ?
C17 N1 C18 C19 60.0(2) . . . . ?
C17 N2 C2 C1 -1.1(2) . . . . ?
C17 N2 C2 C3 176.15(19) . . . . ?
C17 C30 C31 C26 -158.94(17) . . . . ?
C17 C30 C31 C32 20.9(3) . . . . ?
C18 N1 C1 C2 -169.03(18) . . . . ?
C18 N1 C1 C14 19.5(3) . . . . ?
C18 N1 C17 N2 169.25(17) . . . . ?
C18 N1 C17 C30 -11.9(3) . . . . ?
C18 C19 C20 C21 -179.25(18) . . . . ?
C18 C19 C32 C23 -176.95(18) . . . . ?
C18 C19 C32 C31 -4.7(3) . . . . ?
C19 C20 C21 C22 -3.0(3) . . . . ?
C20 C19 C32 C23 0.9(3) . . . . ?
C20 C19 C32 C31 173.12(18) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C21 C22 C23 C24 -172.4(2) . . . . ?
C21 C22 C23 C32 3.6(3) . . . . ?
C22 C23 C24 C25 170.7(2) . . . . ?
C22 C23 C32 C19 -3.9(3) . . . . ?
C22 C23 C32 C31 -176.70(18) . . . . ?
C23 C24 C25 C26 3.6(3) . . . . ?
C24 C23 C32 C19 172.03(18) . . . . ?
C24 C23 C32 C31 -0.8(3) . . . . ?
C24 C25 C26 C27 -178.8(2) . . . . ?
C24 C25 C26 C31 4.3(3) . . . . ?
C25 C26 C27 C28 -176.50(19) . . . . ?
C25 C26 C31 C30 169.70(18) . . . . ?
C25 C26 C31 C32 -10.1(3) . . . . ?
C26 C27 C28 C29 4.3(3) . . . . ?
C26 C31 C32 C19 -163.87(18) . . . . ?
C26 C31 C32 C23 8.3(3) . . . . ?
C27 C26 C31 C30 -7.1(3) . . . . ?
C27 C26 C31 C32 173.01(18) . . . . ?
C27 C28 C29 C30 -1.9(3) . . . . ?
C28 C29 C30 C17 164.09(18) . . . . ?
C28 C29 C30 C31 -5.3(3) . . . . ?
C29 C30 C31 C26 9.5(3) . . . . ?
C29 C30 C31 C32 -170.65(18) . . . . ?
C30 C31 C32 C19 16.3(3) . . . . ?
C30 C31 C32 C23 -171.54(18) . . . . ?
C31 C26 C27 C28 0.4(3) . . . . ?
C32 C19 C20 C21 2.6(3) . . . . ?
C32 C23 C24 C25 -5.3(3) . . . . ?

_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 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.832
####################################################################### 
# 
# 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_re50-2
_database_code_depnum_ccdc_archive 'CCDC 2256234'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2026-01-26 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H16 N2 O'
_chemical_formula_sum            'C32 H16 N2 O'
_chemical_formula_weight         444.47
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C32H16N2O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   3.95070(10)
_cell_length_b                   17.9552(4)
_cell_length_c                   13.8102(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.658(2)
_cell_angle_gamma                90
_cell_volume                     973.03(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.8080
_cell_measurement_theta_min      4.0440
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.032
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19374
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.388
_diffrn_reflns_theta_min         2.461
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -38.00   0.50    5.00    --  -48.31 -42.00  -7.00  164
  2  ω    -40.00  23.00   0.50    5.00    --  -48.31  42.00 144.00  126
  3  ω    -23.00  54.00   0.50    5.00    --   48.31 -42.00  -7.00  154
  4  ω     38.00 120.00   0.50    5.00    --   48.31  42.00 144.00  164
  5  ω   -161.00 -79.00   0.50   35.00    --  -90.00 -42.00  -7.00  164
  6  ω    101.00 178.00   0.50   35.00    --  111.50  42.00 144.00  154
  7  ω   -119.00 -34.00   0.50    5.00    --  -48.31 -57.00-120.00  170
  8  ω   -120.00 -38.00   0.50    5.00    --  -48.31 -40.00 -93.77  164
  9  ω   -119.00 -73.00   0.50    5.00    --  -48.31-125.00  60.00   92
 10  ω   -119.00 -27.00   0.50    5.00    --  -48.31 -77.00-150.00  184
 11  ω     38.00 121.00   0.50    5.00    --   48.31  37.00-120.00  166
 12  ω     34.00  95.00   0.50    5.00    --   48.31-125.00-120.00  122
 13  ω   -161.00 -72.00   0.50   35.00    --  -90.00 -68.00-138.68  178
 14  ω   -161.00 -69.00   0.50   35.00    --  -90.00 -74.00 -53.28  184
 15  ω   -161.00 -69.00   0.50   35.00    --  -90.00 -74.00 -81.43  184
 16  ω   -161.00 -68.00   0.50   35.00    --  -90.00 -77.00 -60.00  186
 17  ω   -161.00 -70.00   0.50   35.00    --  -90.00 -72.00 -78.48  182
 18  ω   -161.00 -70.00   0.50   35.00    --  -90.00 -73.00-117.10  182
 19  ω   -161.00 -71.00   0.50   35.00    --  -90.00 -69.00-109.81  180
 20  ω    -65.00 -18.00   0.50   35.00    --  -90.00  61.00 -30.00   94
 21  ω   -161.00 -69.00   0.50   35.00    --  -90.00 -74.00-106.89  184
 22  ω   -130.00 -71.00   0.50   35.00    --  -90.00 -72.00-104.05  118
 23  ω   -104.00 -78.00   0.50   35.00    --  -90.00 -65.00-158.95   52
 24  ω   -100.00 -69.00   0.50   35.00    --  -90.00 -77.00 -90.00   62
 25  ω     40.00  97.00   0.50   35.00    --  111.50-125.00 -30.00  114
 26  ω     91.00 173.00   0.50   35.00    --  111.50  77.00 -60.00  164
 27  ω    135.00 161.00   0.50   35.00    --  111.50  30.00-150.00   52
 28  ω    105.00 134.00   0.50   35.00    --  111.50  30.00-150.00   58
 29  ω    153.00 178.00   0.50   35.00    --  111.50 125.00  30.00   50
 30  ω     96.00 145.00   0.50   35.00    --  111.50 125.00  30.00   98
 31  ω    105.00 161.00   0.50   35.00    --  111.50  45.00-120.00  112
 32  ω     91.00 116.00   0.50   35.00    --  111.50  77.00-120.00   50
 33  ω     49.00  74.00   0.50   35.00    --  111.50 -61.00   0.00   50
 34  ω     44.00  73.00   0.50   35.00    --  111.50 -61.00 150.00   58
 35  ω    142.00 169.00   0.50   35.00    --  111.50  15.00  30.00   54
 36  ω    103.00 148.00   0.50   35.00    --  111.50  30.00 120.00   90
 37  ω    101.00 137.00   0.50   35.00    --  111.50  15.00  30.00   72
 38  ω     94.00 123.00   0.50   35.00    --  111.50  77.00-180.00   58
 39  ω     40.00  84.00   0.50   35.00    --  111.50-125.00 -60.00   88
 40  ω    145.00 174.00   0.50   35.00    --  111.50  45.00-180.00   58
 41  ω     40.00  65.00   0.50   35.00    --  111.50 -61.00 -30.00   50
 42  ω     97.00 122.00   0.50   35.00    --  111.50  61.00-150.00   50
 43  ω    101.00 135.00   0.50   35.00    --  111.50  61.00-120.00   68
 44  ω    153.00 178.00   0.50   35.00    --  111.50  61.00-120.00   50
 45  ω     96.00 123.00   0.50   35.00    --  111.50  61.00 -90.00   54
 46  ω     70.00  96.00   0.50   35.00    --  111.50 -94.00  60.00   52
 47  ω    102.00 142.00   0.50   35.00    --  111.50  45.00 120.00   80
 48  ω     93.00 174.00   0.50   35.00    --  111.50  77.00 -90.00  162
 49  ω     79.00 105.00   0.50   35.00    --  111.50 -94.00   0.00   52
 50  ω     45.00  71.00   0.50   35.00    --  111.50 -94.00   0.00   52
 51  ω     40.00  65.00   0.50   35.00    --  111.50 -61.00-120.00   50
 52  ω     40.00  87.00   0.50   35.00    --  111.50 -94.00 120.00   94
 53  ω     49.00  78.00   0.50   35.00    --  111.50 -61.00-180.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1947850000
_diffrn_orient_matrix_UB_12      -0.0166041000
_diffrn_orient_matrix_UB_13      -0.1009226000
_diffrn_orient_matrix_UB_21      -0.2724015000
_diffrn_orient_matrix_UB_22      -0.0427428000
_diffrn_orient_matrix_UB_23      0.0489925000
_diffrn_orient_matrix_UB_31      -0.2046131000
_diffrn_orient_matrix_UB_32      0.0725432000
_diffrn_orient_matrix_UB_33      0.0057797000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.862
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                3173
_reflns_number_total             3747
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0734P)²+0.3173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1424
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
# end Validation Reply Form
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(9)
 0.1(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C16A) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C14A) \\sim Ueq,
Uanis(C12A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C19A) \\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C21A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C21) = Uanis(C11A)
Uanis(C15A) = Uanis(C32)
4. Others
 Sof(O1A)=Sof(N1A)=Sof(C17A)=Sof(C16A)=Sof(N2A)=Sof(C14A)=Sof(C1A)=Sof(C15A)=
 Sof(C13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=
 Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(O1)=Sof(N1)=Sof(N2)=Sof(C1)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=
 Sof(H12)=Sof(C13)=Sof(C14)=Sof(C17)=Sof(C18)=Sof(C19)=Sof(C20)=Sof(H20)=
 Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C32)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C12A(H12A), C11A(H11A), C10A(H10A),
 C19A(H19A), C20A(H20A), C21A(H21A), C24(H24), C25(H25), C27(H27), C28(H28),
 C29(H29), C10(H10), C11(H11), C12(H12), C20(H20), C21(H21), C22(H22)
5.b Fitted pentagon refined as free rotating group:
 N1A(C17A,C16A,N2A,C14A)
5.c Fitted hexagon refined as free rotating group:
 C15A(C13A,C12A,C11A,C10A,C23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3860(12) 0.1173(2) 0.4359(3) 0.0446(12) Uani 0.699(6) 1 d . . P A 1
O1A O 0.625(3) 0.3848(6) 0.5531(8) 0.049(3) Uani 0.301(6) 1 d . . P A 2
N1A N 0.488(3) 0.2764(5) 0.4766(10) 0.039(4) Uani 0.301(6) 1 d G . P A 2
C17A C 0.498(3) 0.2307(7) 0.5609(8) 0.045(5) Uani 0.301(6) 1 d G U P A 2
C16A C 0.615(4) 0.1590(6) 0.5366(7) 0.066(8) Uani 0.301(6) 1 d G U P A 2
N2A N 0.677(3) 0.1604(5) 0.4373(7) 0.034(3) Uani 0.301(6) 1 d G . P A 2
C14A C 0.599(3) 0.2329(6) 0.4003(7) 0.040(4) Uani 0.301(6) 1 d G U P A 2
C1A C 0.497(6) 0.3519(10) 0.4764(14) 0.032(4) Uani 0.301(6) 1 d . . P A 2
C2 C 0.6550(11) 0.1045(2) 0.5982(3) 0.0382(10) Uani 1 1 d . . . . .
C3 C 0.8074(12) 0.0391(3) 0.5703(3) 0.0430(10) Uani 1 1 d . . . . .
H3 H 0.826542 0.030794 0.503215 0.052 Uiso 1 1 calc R U . . .
C4 C 0.9293(14) -0.0132(3) 0.6367(4) 0.0504(12) Uani 1 1 d . . . . .
H4 H 1.036980 -0.056841 0.616402 0.060 Uiso 1 1 calc R U . . .
C5 C 0.8951(14) -0.0022(3) 0.7324(4) 0.0493(11) Uani 1 1 d . . . . .
H5 H 0.982367 -0.038507 0.778727 0.059 Uiso 1 1 calc R U . . .
C6 C 0.7347(11) 0.0614(2) 0.7648(3) 0.0389(10) Uani 1 1 d . . . . .
C7 C 0.6825(12) 0.0666(2) 0.8652(3) 0.0427(11) Uani 1 1 d . . . . .
H7 H 0.765814 0.028189 0.908971 0.051 Uiso 1 1 calc R U . . .
C8 C 0.5190(12) 0.1243(3) 0.8985(3) 0.0448(11) Uani 1 1 d . . . . .
H8 H 0.479026 0.125429 0.964978 0.054 Uiso 1 1 calc R U . . .
C9 C 0.4019(11) 0.1851(3) 0.8353(3) 0.0409(10) Uani 1 1 d . . . . .
C15 C 0.4586(11) 0.1844(2) 0.7357(3) 0.0381(10) Uani 1 1 d . . . . .
C15A C 0.548(3) 0.3031(6) 0.2576(4) 0.0267(11) Uani 0.301(6) 1 d G . P A 2
C13A C 0.682(5) 0.2408(8) 0.3080(7) 0.062(8) Uani 0.301(6) 1 d G . P A 2
C12A C 0.861(4) 0.1879(6) 0.2609(11) 0.061(8) Uani 0.301(6) 1 d G U P A 2
H12A H 0.952322 0.145309 0.295384 0.074 Uiso 0.301(6) 1 calc R U P A 2
C11A C 0.907(3) 0.1974(5) 0.1634(11) 0.0431(19) Uani 0.301(6) 1 d G . P A 2
H11A H 1.029055 0.161340 0.131196 0.052 Uiso 0.301(6) 1 calc R U P A 2
C10A C 0.773(3) 0.2598(5) 0.1130(6) 0.031(5) Uani 0.301(6) 1 d G . P A 2
H10A H 0.803926 0.266313 0.046329 0.037 Uiso 0.301(6) 1 calc R U P A 2
C23 C 0.5935(12) 0.3126(2) 0.1601(3) 0.0433(11) Uani 1 1 d G . . . .
C16 C 0.6182(10) 0.1193(2) 0.6979(3) 0.0342(9) Uani 1 1 d . . . . .
C18A C 0.385(6) 0.2484(15) 0.6559(12) 0.025(5) Uani 0.301(6) 1 d . . P A 2
C19A C 0.225(5) 0.3067(10) 0.6896(16) 0.042(4) Uani 0.301(6) 1 d . U P A 2
H19A H 0.160419 0.346873 0.646735 0.051 Uiso 0.301(6) 1 calc R U P A 2
C20A C 0.146(5) 0.3108(12) 0.7893(19) 0.038(5) Uani 0.301(6) 1 d . U P A 2
H20A H 0.025020 0.352913 0.808668 0.046 Uiso 0.301(6) 1 calc R U P A 2
C21A C 0.239(7) 0.2570(14) 0.8564(17) 0.037(5) Uani 0.301(6) 1 d . U P A 2
H21A H 0.197242 0.266058 0.921660 0.045 Uiso 0.301(6) 1 calc R U P A 2
C24 C 0.4902(12) 0.3707(3) 0.0943(3) 0.0468(12) Uani 1 1 d . . . . .
H24 H 0.533236 0.366374 0.028315 0.056 Uiso 1 1 calc R U . . .
C25 C 0.3333(13) 0.4318(3) 0.1225(3) 0.0464(11) Uani 1 1 d . . . . .
H25 H 0.257017 0.468816 0.075878 0.056 Uiso 1 1 calc R U . . .
C26 C 0.2799(11) 0.4416(3) 0.2227(3) 0.0394(10) Uani 1 1 d . . . . .
C27 C 0.1341(14) 0.5078(3) 0.2528(4) 0.0486(11) Uani 1 1 d . . . . .
H27 H 0.065380 0.545335 0.206080 0.058 Uiso 1 1 calc R U . . .
C28 C 0.0899(14) 0.5190(3) 0.3489(4) 0.0490(12) Uani 1 1 d . . . . .
H28 H -0.012794 0.563605 0.368139 0.059 Uiso 1 1 calc R U . . .
C29 C 0.1936(12) 0.4658(3) 0.4172(3) 0.0423(10) Uani 1 1 d . . . . .
H29 H 0.169877 0.474794 0.483837 0.051 Uiso 1 1 calc R U . . .
C30 C 0.3341(11) 0.3984(3) 0.3901(3) 0.0390(10) Uani 1 1 d . . . . .
C31 C 0.3797(10) 0.3847(2) 0.2914(3) 0.0336(9) Uani 1 1 d . . . . .
N1 N 0.5171(14) 0.2270(3) 0.5125(5) 0.0355(13) Uani 0.699(6) 1 d . . P A 1
N2 N 0.3360(13) 0.3380(3) 0.5537(4) 0.0345(12) Uani 0.699(6) 1 d . . P A 1
C1 C 0.502(2) 0.1483(4) 0.5114(5) 0.0373(16) Uani 0.699(6) 1 d . . P A 1
C10 C 0.233(3) 0.2385(6) 0.8845(7) 0.039(2) Uani 0.699(6) 1 d . . P A 1
H10 H 0.201804 0.232970 0.951280 0.047 Uiso 0.699(6) 1 calc R U P A 1
C11 C 0.112(2) 0.3000(4) 0.8313(6) 0.0349(15) Uani 0.699(6) 1 d . . P A 1
H11 H -0.007126 0.338281 0.860642 0.042 Uiso 0.699(6) 1 calc R U P A 1
C12 C 0.1687(17) 0.3049(4) 0.7349(7) 0.0310(15) Uani 0.699(6) 1 d . . P A 1
H12 H 0.086017 0.347199 0.698124 0.037 Uiso 0.699(6) 1 calc R U P A 1
C13 C 0.344(3) 0.2495(7) 0.6892(6) 0.0312(19) Uani 0.699(6) 1 d . . P A 1
C14 C 0.4043(15) 0.2721(3) 0.5877(5) 0.0336(14) Uani 0.699(6) 1 d . . P A 1
C17 C 0.390(2) 0.3372(5) 0.4553(6) 0.0352(19) Uani 0.699(6) 1 d . . P A 1
C18 C 0.5064(16) 0.2707(4) 0.4294(6) 0.0327(16) Uani 0.699(6) 1 d . . P A 1
C19 C 0.6022(19) 0.2583(4) 0.3282(6) 0.0324(17) Uani 0.699(6) 1 d . . P A 1
C20 C 0.773(2) 0.1951(4) 0.3001(6) 0.0407(17) Uani 0.699(6) 1 d . . P A 1
H20 H 0.836483 0.156811 0.346116 0.049 Uiso 0.699(6) 1 calc R U P A 1
C21 C 0.845(2) 0.1886(4) 0.2094(7) 0.0431(19) Uani 0.699(6) 1 d . . P A 1
H21 H 0.961256 0.145229 0.191827 0.052 Uiso 0.699(6) 1 calc R U P A 1
C22 C 0.758(3) 0.2417(5) 0.1395(8) 0.051(3) Uani 0.699(6) 1 d . . P A 1
H22 H 0.806435 0.232240 0.074820 0.061 Uiso 0.699(6) 1 calc R U P A 1
C32 C 0.5265(19) 0.3217(3) 0.2601(4) 0.0267(11) Uani 0.699(6) 1 d . . P A 1


_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 C1 1.224(9) . ?
O1A C1A 1.27(2) . ?
N1A C17A 1.4200 . ?
N1A C14A 1.4200 . ?
N1A C1A 1.36(2) . ?
C17A C16A 1.4200 . ?
C17A C18A 1.47(2) . ?
C16A N2A 1.4200 . ?
C16A C2 1.295(9) . ?
N2A C14A 1.4200 . ?
C14A C13A 1.359(14) . ?
C1A C30 1.53(2) . ?
C2 C3 1.394(6) . ?
C2 C16 1.425(6) . ?
C2 C1 1.501(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.360(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.358(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(7) . ?
C6 C7 1.428(6) . ?
C6 C16 1.431(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.331(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.439(7) . ?
C9 C15 1.419(6) . ?
C9 C21A 1.49(3) . ?
C9 C10 1.390(13) . ?
C15 C16 1.455(6) . ?
C15 C18A 1.60(2) . ?
C15 C13 1.383(14) . ?
C15A C13A 1.3900 . ?
C15A C23 1.3900 . ?
C15A C31 1.696(10) . ?
C13A C12A 1.3900 . ?
C12A H12A 0.9500 . ?
C12A C11A 1.3900 . ?
C11A H11A 0.9500 . ?
C11A C10A 1.3900 . ?
C10A H10A 0.9500 . ?
C10A C23 1.3900 . ?
C23 C24 1.412(7) . ?
C23 C22 1.473(11) . ?
C23 C32 1.445(8) . ?
C18A C19A 1.33(4) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.45(3) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.36(3) . ?
C21A H21A 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.339(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.435(7) . ?
C26 C27 1.404(7) . ?
C26 C31 1.418(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.374(7) . ?
C28 H28 0.9500 . ?
C28 C29 1.370(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.400(6) . ?
C30 C31 1.417(6) . ?
C30 C17 1.422(10) . ?
C31 C32 1.364(7) . ?
N1 C1 1.415(9) . ?
N1 C14 1.428(8) . ?
N1 C18 1.386(8) . ?
N2 C14 1.291(7) . ?
N2 C17 1.400(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.404(14) . ?
C13 C14 1.504(9) . ?
C17 C18 1.343(12) . ?
C18 C19 1.506(12) . ?
C19 C20 1.398(9) . ?
C19 C32 1.486(9) . ?
C20 H20 0.9500 . ?
C20 C21 1.321(12) . ?
C21 H21 0.9500 . ?
C21 C22 1.371(13) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14A N1A C17A 108.0 . . ?
C1A N1A C17A 125.5(13) . . ?
C1A N1A C14A 122.5(13) . . ?
N1A C17A C18A 128.6(13) . . ?
C16A C17A N1A 108.0 . . ?
C16A C17A C18A 123.2(13) . . ?
C17A C16A N2A 108.0 . . ?
C2 C16A C17A 123.2(9) . . ?
C2 C16A N2A 128.8(9) . . ?
C14A N2A C16A 108.0 . . ?
N1A C14A N2A 108.0 . . ?
C13A C14A N1A 140.1(10) . . ?
C13A C14A N2A 111.5(10) . . ?
O1A C1A N1A 118.2(17) . . ?
O1A C1A C30 119.1(14) . . ?
N1A C1A C30 122.5(14) . . ?
C16A C2 C3 118.6(6) . . ?
C16A C2 C16 118.4(7) . . ?
C3 C2 C16 121.3(4) . . ?
C3 C2 C1 111.5(5) . . ?
C16 C2 C1 126.7(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.9(5) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 118.9(4) . . ?
C5 C6 C16 120.5(4) . . ?
C7 C6 C16 120.6(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(4) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.1(4) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C21A 131.0(10) . . ?
C15 C9 C8 120.4(4) . . ?
C15 C9 C21A 108.5(10) . . ?
C10 C9 C8 111.5(5) . . ?
C10 C9 C15 128.1(5) . . ?
C9 C15 C16 118.6(4) . . ?
C9 C15 C18A 128.9(10) . . ?
C16 C15 C18A 112.5(10) . . ?
C13 C15 C9 111.3(5) . . ?
C13 C15 C16 130.1(5) . . ?
C13A C15A C23 120.0 . . ?
C13A C15A C31 134.2(5) . . ?
C23 C15A C31 105.0(5) . . ?
C14A C13A C15A 115.7(10) . . ?
C14A C13A C12A 124.0(10) . . ?
C12A C13A C15A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C23 C10A C11A 120.0 . . ?
C23 C10A H10A 120.0 . . ?
C15A C23 C24 130.8(5) . . ?
C10A C23 C15A 120.0 . . ?
C10A C23 C24 109.1(5) . . ?
C24 C23 C22 128.0(6) . . ?
C24 C23 C32 117.4(4) . . ?
C32 C23 C22 114.6(6) . . ?
C2 C16 C6 115.3(4) . . ?
C2 C16 C15 126.4(4) . . ?
C6 C16 C15 118.2(4) . . ?
C17A C18A C15 114.2(19) . . ?
C19A C18A C17A 133(2) . . ?
C19A C18A C15 112.3(14) . . ?
C18A C19A H19A 118.8 . . ?
C18A C19A C20A 122.4(18) . . ?
C20A C19A H19A 118.8 . . ?
C19A C20A H20A 118.7 . . ?
C21A C20A C19A 122.7(18) . . ?
C21A C20A H20A 118.7 . . ?
C9 C21A H21A 117.5 . . ?
C20A C21A C9 125.0(18) . . ?
C20A C21A H21A 117.5 . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.8(4) . . ?
C25 C24 H24 119.1 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 120.0(4) . . ?
C27 C26 C31 120.3(4) . . ?
C31 C26 C25 119.7(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.7(4) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.1(4) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.0(4) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 C1A 113.9(8) . . ?
C29 C30 C31 120.4(4) . . ?
C29 C30 C17 122.4(5) . . ?
C31 C30 C1A 124.4(8) . . ?
C31 C30 C17 116.6(5) . . ?
C26 C31 C15A 121.8(4) . . ?
C30 C31 C15A 120.8(4) . . ?
C30 C31 C26 117.5(4) . . ?
C32 C31 C26 118.8(4) . . ?
C32 C31 C30 123.7(4) . . ?
C1 N1 C14 123.8(6) . . ?
C18 N1 C1 124.0(6) . . ?
C18 N1 C14 107.5(6) . . ?
C14 N2 C17 107.2(6) . . ?
O1 C1 C2 121.2(6) . . ?
O1 C1 N1 118.3(6) . . ?
N1 C1 C2 120.2(6) . . ?
C9 C10 H10 121.7 . . ?
C11 C10 C9 116.6(8) . . ?
C11 C10 H10 121.7 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.7(7) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 118.9 . . ?
C11 C12 C13 122.2(7) . . ?
C13 C12 H12 118.9 . . ?
C15 C13 C12 122.8(7) . . ?
C15 C13 C14 125.6(8) . . ?
C12 C13 C14 111.5(10) . . ?
N1 C14 C13 128.5(6) . . ?
N2 C14 N1 108.9(6) . . ?
N2 C14 C13 122.5(7) . . ?
N2 C17 C30 125.3(8) . . ?
C18 C17 C30 123.4(8) . . ?
C18 C17 N2 111.3(8) . . ?
N1 C18 C19 134.2(6) . . ?
C17 C18 N1 105.1(7) . . ?
C17 C18 C19 120.6(7) . . ?
C20 C19 C18 124.0(7) . . ?
C20 C19 C32 121.0(7) . . ?
C32 C19 C18 114.9(6) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.9(8) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 118.6 . . ?
C20 C21 C22 122.8(8) . . ?
C22 C21 H21 118.6 . . ?
C23 C22 H22 118.5 . . ?
C21 C22 C23 123.0(9) . . ?
C21 C22 H22 118.5 . . ?
C23 C32 C19 118.2(6) . . ?
C31 C32 C23 121.9(5) . . ?
C31 C32 C19 119.8(6) . . ?

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
O1A C1A C30 C29 -30(2) . . . . ?
O1A C1A C30 C31 136.9(15) . . . . ?
N1A C17A C16A N2A 0.0 . . . . ?
N1A C17A C16A C2 179.4(15) . . . . ?
N1A C17A C18A C15 -176.3(11) . . . . ?
N1A C17A C18A C19A 5(3) . . . . ?
N1A C14A C13A C15A -22(2) . . . . ?
N1A C14A C13A C12A 163.7(10) . . . . ?
N1A C1A C30 C29 145.5(16) . . . . ?
N1A C1A C30 C31 -48(2) . . . . ?
C17A N1A C14A N2A 0.0 . . . . ?
C17A N1A C14A C13A -172(2) . . . . ?
C17A N1A C1A O1A 23(3) . . . . ?
C17A N1A C1A C30 -152.4(13) . . . . ?
C17A C16A N2A C14A 0.0 . . . . ?
C17A C16A C2 C3 -172.8(6) . . . . ?
C17A C16A C2 C16 -7.4(12) . . . . ?
C17A C18A C19A C20A -178.8(19) . . . . ?
C16A C17A C18A C15 9(2) . . . . ?
C16A C17A C18A C19A -169.1(18) . . . . ?
C16A N2A C14A N1A 0.0 . . . . ?
C16A N2A C14A C13A 174.3(14) . . . . ?
C16A C2 C3 C4 164.5(9) . . . . ?
C16A C2 C16 C6 -167.4(8) . . . . ?
C16A C2 C16 C15 16.3(10) . . . . ?
N2A C16A C2 C3 6.5(16) . . . . ?
N2A C16A C2 C16 171.9(9) . . . . ?
N2A C14A C13A C15A 166.3(7) . . . . ?
N2A C14A C13A C12A -7.9(17) . . . . ?
C14A N1A C17A C16A 0.0 . . . . ?
C14A N1A C17A C18A -175.0(17) . . . . ?
C14A N1A C1A O1A -131.7(16) . . . . ?
C14A N1A C1A C30 53(2) . . . . ?
C14A C13A C12A C11A 173.9(19) . . . . ?
C1A N1A C17A C16A -157.9(17) . . . . ?
C1A N1A C17A C18A 27(2) . . . . ?
C1A N1A C14A N2A 158.7(16) . . . . ?
C1A N1A C14A C13A -13(2) . . . . ?
C1A C30 C31 C15A 14.1(12) . . . . ?
C1A C30 C31 C26 -165.9(10) . . . . ?
C2 C16A N2A C14A -179.4(16) . . . . ?
C2 C3 C4 C5 1.5(8) . . . . ?
C3 C2 C16 C6 -2.5(6) . . . . ?
C3 C2 C16 C15 -178.7(4) . . . . ?
C3 C2 C1 O1 31.5(9) . . . . ?
C3 C2 C1 N1 -142.9(6) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 C7 174.9(5) . . . . ?
C4 C5 C6 C16 -3.7(8) . . . . ?
C5 C6 C7 C8 -177.2(4) . . . . ?
C5 C6 C16 C2 4.4(6) . . . . ?
C5 C6 C16 C15 -179.0(4) . . . . ?
C6 C7 C8 C9 -2.7(7) . . . . ?
C7 C6 C16 C2 -174.1(4) . . . . ?
C7 C6 C16 C15 2.5(6) . . . . ?
C7 C8 C9 C15 0.1(7) . . . . ?
C7 C8 C9 C21A -174.9(14) . . . . ?
C7 C8 C9 C10 178.9(6) . . . . ?
C8 C9 C15 C16 3.7(6) . . . . ?
C8 C9 C15 C18A -173.5(11) . . . . ?
C8 C9 C15 C13 -176.6(6) . . . . ?
C8 C9 C21A C20A 178.5(15) . . . . ?
C8 C9 C10 C11 179.2(7) . . . . ?
C9 C15 C16 C2 171.3(4) . . . . ?
C9 C15 C16 C6 -4.9(6) . . . . ?
C9 C15 C18A C17A 175.8(9) . . . . ?
C9 C15 C18A C19A -5(2) . . . . ?
C9 C15 C13 C12 -5.2(11) . . . . ?
C9 C15 C13 C14 171.5(7) . . . . ?
C9 C10 C11 C12 -0.6(13) . . . . ?
C15 C9 C21A C20A 3(3) . . . . ?
C15 C9 C10 C11 -2.1(12) . . . . ?
C15 C18A C19A C20A 3(3) . . . . ?
C15 C13 C14 N1 15.2(14) . . . . ?
C15 C13 C14 N2 -169.3(7) . . . . ?
C15A C13A C12A C11A 0.0 . . . . ?
C15A C23 C24 C25 3.6(11) . . . . ?
C13A C15A C23 C10A 0.0 . . . . ?
C13A C15A C23 C24 -178.7(7) . . . . ?
C13A C15A C31 C26 176.0(5) . . . . ?
C13A C15A C31 C30 -4.0(8) . . . . ?
C13A C12A C11A C10A 0.0 . . . . ?
C12A C11A C10A C23 0.0 . . . . ?
C11A C10A C23 C15A 0.0 . . . . ?
C11A C10A C23 C24 178.9(6) . . . . ?
C10A C23 C24 C25 -175.2(6) . . . . ?
C23 C15A C13A C14A -174.4(17) . . . . ?
C23 C15A C13A C12A 0.0 . . . . ?
C23 C15A C31 C26 7.0(11) . . . . ?
C23 C15A C31 C30 -172.9(6) . . . . ?
C23 C24 C25 C26 3.1(8) . . . . ?
C16 C2 C3 C4 -0.4(7) . . . . ?
C16 C2 C1 O1 -140.3(6) . . . . ?
C16 C2 C1 N1 45.4(10) . . . . ?
C16 C6 C7 C8 1.4(7) . . . . ?
C16 C15 C18A C17A -1.6(17) . . . . ?
C16 C15 C18A C19A 177.3(12) . . . . ?
C16 C15 C13 C12 174.5(6) . . . . ?
C16 C15 C13 C14 -8.9(13) . . . . ?
C18A C17A C16A N2A 175.4(16) . . . . ?
C18A C17A C16A C2 -5.2(15) . . . . ?
C18A C15 C16 C2 -11.0(10) . . . . ?
C18A C15 C16 C6 172.8(9) . . . . ?
C18A C19A C20A C21A 2(3) . . . . ?
C19A C20A C21A C9 -6(3) . . . . ?
C21A C9 C15 C16 179.7(11) . . . . ?
C21A C9 C15 C18A 2.5(15) . . . . ?
C24 C23 C22 C21 -179.3(6) . . . . ?
C24 C23 C32 C31 -2.1(9) . . . . ?
C24 C23 C32 C19 174.2(5) . . . . ?
C24 C25 C26 C27 176.1(5) . . . . ?
C24 C25 C26 C31 -2.9(7) . . . . ?
C25 C26 C27 C28 -178.2(4) . . . . ?
C25 C26 C31 C15A -2.5(8) . . . . ?
C25 C26 C31 C30 177.5(4) . . . . ?
C25 C26 C31 C32 0.3(7) . . . . ?
C26 C27 C28 C29 1.1(8) . . . . ?
C26 C31 C32 C23 2.2(8) . . . . ?
C26 C31 C32 C19 -174.0(5) . . . . ?
C27 C26 C31 C15A 178.5(7) . . . . ?
C27 C26 C31 C30 -1.5(6) . . . . ?
C27 C26 C31 C32 -178.7(5) . . . . ?
C27 C28 C29 C30 -2.4(8) . . . . ?
C28 C29 C30 C1A 169.2(10) . . . . ?
C28 C29 C30 C31 1.6(7) . . . . ?
C28 C29 C30 C17 -168.8(5) . . . . ?
C29 C30 C31 C15A -179.7(7) . . . . ?
C29 C30 C31 C26 0.3(6) . . . . ?
C29 C30 C31 C32 177.4(5) . . . . ?
C29 C30 C17 N2 -4.7(10) . . . . ?
C29 C30 C17 C18 176.2(6) . . . . ?
C30 C31 C32 C23 -174.8(5) . . . . ?
C30 C31 C32 C19 9.0(8) . . . . ?
C30 C17 C18 N1 -178.8(6) . . . . ?
C30 C17 C18 C19 2.8(10) . . . . ?
C31 C15A C13A C14A 18.0(11) . . . . ?
C31 C15A C13A C12A -167.6(12) . . . . ?
C31 C15A C23 C10A 170.8(9) . . . . ?
C31 C15A C23 C24 -7.8(13) . . . . ?
C31 C26 C27 C28 0.8(8) . . . . ?
C31 C30 C17 N2 -175.5(6) . . . . ?
C31 C30 C17 C18 5.4(9) . . . . ?
N1 C18 C19 C20 -7.8(12) . . . . ?
N1 C18 C19 C32 176.8(6) . . . . ?
N2 C17 C18 N1 2.0(7) . . . . ?
N2 C17 C18 C19 -176.4(6) . . . . ?
C1 C2 C3 C4 -172.7(5) . . . . ?
C1 C2 C16 C6 168.6(5) . . . . ?
C1 C2 C16 C15 -7.7(7) . . . . ?
C1 N1 C14 N2 -157.5(6) . . . . ?
C1 N1 C14 C13 18.5(11) . . . . ?
C1 N1 C18 C17 155.7(7) . . . . ?
C1 N1 C18 C19 -26.2(11) . . . . ?
C10 C9 C15 C16 -174.9(7) . . . . ?
C10 C9 C15 C13 4.8(9) . . . . ?
C10 C11 C12 C13 0.0(12) . . . . ?
C11 C12 C13 C15 3.3(13) . . . . ?
C11 C12 C13 C14 -173.8(7) . . . . ?
C12 C13 C14 N1 -167.8(6) . . . . ?
C12 C13 C14 N2 7.6(11) . . . . ?
C13 C15 C16 C2 -8.3(9) . . . . ?
C13 C15 C16 C6 175.5(7) . . . . ?
C14 N1 C1 O1 132.7(7) . . . . ?
C14 N1 C1 C2 -52.8(10) . . . . ?
C14 N1 C18 C17 -0.7(6) . . . . ?
C14 N1 C18 C19 177.4(7) . . . . ?
C14 N2 C17 C30 178.2(7) . . . . ?
C14 N2 C17 C18 -2.7(7) . . . . ?
C17 C30 C31 C26 171.3(5) . . . . ?
C17 C30 C31 C32 -11.6(7) . . . . ?
C17 N2 C14 N1 2.1(6) . . . . ?
C17 N2 C14 C13 -174.1(7) . . . . ?
C17 C18 C19 C20 169.9(7) . . . . ?
C17 C18 C19 C32 -5.4(9) . . . . ?
C18 N1 C1 O1 -20.0(11) . . . . ?
C18 N1 C1 C2 154.6(6) . . . . ?
C18 N1 C14 N2 -1.0(6) . . . . ?
C18 N1 C14 C13 175.0(7) . . . . ?
C18 C19 C20 C21 179.5(7) . . . . ?
C18 C19 C32 C23 -176.6(6) . . . . ?
C18 C19 C32 C31 -0.3(8) . . . . ?
C19 C20 C21 C22 -0.2(12) . . . . ?
C20 C19 C32 C23 7.9(9) . . . . ?
C20 C19 C32 C31 -175.8(7) . . . . ?
C20 C21 C22 C23 3.4(13) . . . . ?
C22 C23 C24 C25 178.0(6) . . . . ?
C22 C23 C32 C31 179.1(7) . . . . ?
C22 C23 C32 C19 -4.7(8) . . . . ?
C32 C23 C24 C25 -0.6(8) . . . . ?
C32 C23 C22 C21 -0.6(11) . . . . ?
C32 C19 C20 C21 -5.4(11) . . . . ?

_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 2.298
_oxdiff_exptl_absorpt_empirical_full_min 0.408
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(9)
2 0.1(9)

# start Validation Reply Form
_vrf_PLAT089_re50-2              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.81 Note  
RESPONSE: This is due to the restraints/constraints 
on the disorder of whole molecule.
;
