# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_zengwt_210430
_database_code_depnum_ccdc_archive 'CCDC 2094889'
loop_
_audit_author_name
_audit_author_address
'zeng wt'
; School of Pharmaceutical Sciences
China
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-04-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H25 N3 O4'
_chemical_formula_sum            'C29 H25 N3 O4'
_chemical_formula_weight         479.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0511(4)
_cell_length_b                   19.4219(8)
_cell_length_c                   12.2312(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.502(3)
_cell_angle_gamma                90
_cell_volume                     2347.68(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4652
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8830
_cell_measurement_theta_min      3.6150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17966
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.199
_diffrn_reflns_theta_min         4.324
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     84.00 122.00   0.50    1.50    --  105.44 117.00  84.00   76
  2  ω     75.00 103.00   0.50    0.20    --   46.62 163.00-126.00   56
  3  ω     80.00 105.00   0.50    1.50    --  105.44 163.00-126.00   50
  4  ω    146.00 177.00   0.50    1.50    --  105.44  30.00-180.00   62
  5  ω     91.00 117.00   0.50    1.50    --  105.44  30.00-180.00   52
  6  ω     78.00 103.00   0.50    1.50    --  105.44 -94.00  30.00   50
  7  ω     51.00  89.00   0.50    0.20    --   46.62-117.00  -3.00   76
  8  ω     78.00 103.00   0.50    0.20    --   46.62-163.00-152.00   50
  9  ω     47.00  74.00   0.50    1.50    --  105.44-163.00-152.00   54
 10  ω     35.00 109.00   0.50    1.50    --  105.44-117.00  -3.00  148
 11  ω     48.00 102.00   0.50    1.50    --  105.44 -94.00   0.00  108
 12  ω     45.00 106.00   0.50    1.50    --  105.44 -77.00   0.00  122
 13  ω     33.00  73.00   0.50    1.50    --  105.44 -61.00  30.00   80
 14  ω     33.00  72.00   0.50    1.50    --  105.44 -61.00  60.00   78
 15  ω     35.00  73.00   0.50    1.50    --  105.44 -61.00 120.00   76
 16  ω    -28.00  28.00   0.50    0.20    --   46.62 -19.00  90.00  112
 17  ω     33.00  65.00   0.50    1.50    --  105.44 -61.00   0.00   64
 18  ω    -13.00  26.00   0.50    0.20    --  -46.62  19.00-180.00   78
 19  ω    -23.00  29.00   0.50    0.20    --  -46.62  19.00 -90.00  104
 20  ω    -68.00 -27.00   0.50    1.50    -- -100.00  61.00 -60.00   82
 21  ω    -67.00 -27.00   0.50    1.50    -- -100.00  61.00 -90.00   80
 22  ω   -175.00 -91.00   0.50    1.50    -- -100.00 -30.00-180.00  168
 23  ω    -73.00 -48.00   0.50    0.20    --  -46.62 117.00  84.00   50
 24  ω   -105.00 -67.00   0.50    1.50    -- -100.00 117.00  84.00   76
 25  ω   -130.00 -88.00   0.50    1.50    -- -100.00 -45.00 -90.00   84
 26  ω   -162.00-136.00   0.50    1.50    -- -100.00 -45.00 -90.00   52
 27  ω   -155.00-104.00   0.50    1.50    -- -100.00-117.00  -3.00  102
 28  ω   -113.00 -75.00   0.50    0.20    --  -46.62-125.00  60.00   76
 29  ω   -110.00 -53.00   0.50    0.20    --  -46.62-163.00-152.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0935183000
_diffrn_orient_matrix_UB_12      0.0588905000
_diffrn_orient_matrix_UB_13      -0.0234964000
_diffrn_orient_matrix_UB_21      -0.0843064000
_diffrn_orient_matrix_UB_22      0.0515298000
_diffrn_orient_matrix_UB_23      0.0545543000
_diffrn_orient_matrix_UB_31      0.0920507000
_diffrn_orient_matrix_UB_32      -0.0127163000
_diffrn_orient_matrix_UB_33      0.1135060000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3759
_reflns_number_total             4692
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.0029(5)
_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   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0731
_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)+(0.0949P)²+1.5292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1841
_refine_ls_wR_factor_ref         0.1957
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N17(H17), C30(H30), C5(H5), C8(H8), C29(H29), C16(H16), C23(H23), C15(H15),
 C28(H28), C12(H12), C7(H7), C14(H14), C27(H27), C19(H19), C13(H13), C22(H22),
 C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C)
;
_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
O36 O 0.56470(17) 0.46889(10) 0.36180(13) 0.0274(4) Uani 1 1 d . . . . .
O34 O 0.08826(19) 0.18681(10) 0.31561(14) 0.0310(4) Uani 1 1 d . . . . .
N1 N 0.4649(2) 0.38179(11) 0.24768(15) 0.0236(5) Uani 1 1 d . . . . .
N17 N 0.4344(2) 0.39062(12) 0.52985(15) 0.0263(5) Uani 1 1 d . . . . .
H17 H 0.396779 0.412270 0.577462 0.032 Uiso 1 1 calc R U . . .
O33 O 0.0695(2) 0.47490(14) 0.19084(16) 0.0488(6) Uani 1 1 d . . . . .
O32 O -0.0250(3) 0.37383(15) 0.16879(19) 0.0590(7) Uani 1 1 d . . . . .
C9 C 0.3680(2) 0.33002(13) 0.25224(18) 0.0238(5) Uani 1 1 d . . . . .
N31 N 0.0254(2) 0.42221(16) 0.22748(19) 0.0414(6) Uani 1 1 d . . . . .
C4 C 0.3189(2) 0.33479(13) 0.35157(17) 0.0222(5) Uani 1 1 d . . . . .
C30 C 0.1252(3) 0.43334(13) 0.53804(19) 0.0264(5) Uani 1 1 d . . . . .
H30 H 0.197450 0.445929 0.593284 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4844(2) 0.42155(13) 0.34080(18) 0.0234(5) Uani 1 1 d . . . . .
C5 C 0.2264(2) 0.28767(13) 0.37807(18) 0.0248(5) Uani 1 1 d . . . . .
H5 H 0.195447 0.290499 0.445073 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3249(3) 0.27782(14) 0.17611(18) 0.0273(5) Uani 1 1 d . . . . .
H8 H 0.358372 0.274219 0.110297 0.033 Uiso 1 1 calc R U . . .
C25 C 0.1393(3) 0.43771(13) 0.42654(19) 0.0254(5) Uani 1 1 d . . . . .
C3 C 0.3786(2) 0.39869(13) 0.41235(17) 0.0228(5) Uani 1 1 d . . . . .
C6 C 0.1809(3) 0.23563(13) 0.30106(19) 0.0261(5) Uani 1 1 d . . . . .
C24 C 0.2734(2) 0.45786(14) 0.39811(19) 0.0254(5) Uani 1 1 d . . . . .
H24A H 0.310182 0.496070 0.445172 0.030 Uiso 1 1 calc R U . . .
H24B H 0.258983 0.473687 0.321642 0.030 Uiso 1 1 calc R U . . .
C29 C 0.0061(3) 0.41068(14) 0.5682(2) 0.0303(6) Uani 1 1 d . . . . .
H29 H -0.000785 0.408458 0.642888 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4298(3) 0.41789(14) 0.05090(19) 0.0268(5) Uani 1 1 d . . . . .
C16 C 0.4412(3) 0.39445(15) -0.05477(19) 0.0305(6) Uani 1 1 d . . . . .
H16 H 0.509188 0.363440 -0.062894 0.037 Uiso 1 1 calc R U . . .
C18 C 0.5463(3) 0.34935(15) 0.56865(19) 0.0289(6) Uani 1 1 d . . . . .
C23 C 0.5904(3) 0.29556(15) 0.5093(2) 0.0323(6) Uani 1 1 d . . . . .
H23 H 0.545500 0.286151 0.437430 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3512(3) 0.41717(16) -0.1484(2) 0.0343(6) Uani 1 1 d . . . . .
H15 H 0.360376 0.401847 -0.218633 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5294(3) 0.39413(15) 0.15181(18) 0.0269(5) Uani 1 1 d . . . . .
H10A H 0.572493 0.352021 0.133701 0.032 Uiso 1 1 calc R U . . .
H10B H 0.599200 0.428793 0.170993 0.032 Uiso 1 1 calc R U . . .
C28 C -0.1022(3) 0.39143(15) 0.4878(2) 0.0346(6) Uani 1 1 d . . . . .
H28 H -0.181971 0.376496 0.508485 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3273(3) 0.46407(15) 0.0603(2) 0.0335(6) Uani 1 1 d . . . . .
H12 H 0.319495 0.480727 0.130094 0.040 Uiso 1 1 calc R U . . .
C26 C 0.0273(3) 0.41767(15) 0.3479(2) 0.0297(6) Uani 1 1 d . . . . .
C7 C 0.2308(3) 0.23158(14) 0.20147(19) 0.0298(6) Uani 1 1 d . . . . .
H7 H 0.199631 0.196768 0.151072 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2494(3) 0.46202(16) -0.1370(2) 0.0361(6) Uani 1 1 d . . . . .
H14 H 0.188794 0.476528 -0.199525 0.043 Uiso 1 1 calc R U . . .
C27 C -0.0927(3) 0.39422(15) 0.3768(2) 0.0340(6) Uani 1 1 d . . . . .
H27 H -0.165051 0.380730 0.322299 0.041 Uiso 1 1 calc R U . . .
C35 C 0.0567(3) 0.17967(16) 0.4241(2) 0.0344(6) Uani 1 1 d . . . . .
H35A H -0.002323 0.140910 0.425299 0.052 Uiso 1 1 calc R U . . .
H35B H 0.012546 0.220684 0.442921 0.052 Uiso 1 1 calc R U . . .
H35C H 0.138537 0.172598 0.477091 0.052 Uiso 1 1 calc R U . . .
C19 C 0.6177(3) 0.36266(18) 0.6770(2) 0.0382(7) Uani 1 1 d . . . . .
H19 H 0.590145 0.398494 0.718137 0.046 Uiso 1 1 calc R U . . .
C13 C 0.2363(3) 0.48593(17) -0.0323(2) 0.0366(6) Uani 1 1 d . . . . .
H13 H 0.167094 0.516293 -0.024439 0.044 Uiso 1 1 calc R U . . .
C22 C 0.7005(3) 0.25587(16) 0.5562(3) 0.0381(7) Uani 1 1 d . . . . .
H22 H 0.727654 0.219745 0.515489 0.046 Uiso 1 1 calc R U . . .
C21 C 0.7715(3) 0.26880(17) 0.6631(3) 0.0412(7) Uani 1 1 d . . . . .
H21 H 0.845682 0.242068 0.693994 0.049 Uiso 1 1 calc R U . . .
C20 C 0.7277(3) 0.3233(2) 0.7226(3) 0.0480(8) Uani 1 1 d . . . . .
H20 H 0.773714 0.333001 0.793971 0.058 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
O36 C2 1.220(3) . ?
O34 C6 1.363(3) . ?
O34 C35 1.426(3) . ?
N1 C9 1.408(3) . ?
N1 C2 1.360(3) . ?
N1 C10 1.459(3) . ?
N17 H17 0.8600 . ?
N17 C3 1.453(3) . ?
N17 C18 1.392(3) . ?
O33 N31 1.231(4) . ?
O32 N31 1.234(4) . ?
C9 C4 1.395(3) . ?
C9 C8 1.391(3) . ?
N31 C26 1.472(3) . ?
C4 C5 1.384(4) . ?
C4 C3 1.513(3) . ?
C30 H30 0.9300 . ?
C30 C25 1.399(3) . ?
C30 C29 1.387(4) . ?
C2 C3 1.559(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.380(4) . ?
C25 C24 1.504(3) . ?
C25 C26 1.396(4) . ?
C3 C24 1.550(4) . ?
C6 C7 1.402(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C29 H29 0.9300 . ?
C29 C28 1.379(4) . ?
C11 C16 1.394(3) . ?
C11 C10 1.512(3) . ?
C11 C12 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.395(4) . ?
C18 C23 1.390(4) . ?
C18 C19 1.412(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.385(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.370(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C28 H28 0.9300 . ?
C28 C27 1.379(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(4) . ?
C26 C27 1.395(4) . ?
C7 H7 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.391(4) . ?
C27 H27 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.376(5) . ?
C13 H13 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.394(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.399(5) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O34 C35 117.53(19) . . ?
C9 N1 C10 124.11(19) . . ?
C2 N1 C9 111.56(19) . . ?
C2 N1 C10 124.2(2) . . ?
C3 N17 H17 118.6 . . ?
C18 N17 H17 118.6 . . ?
C18 N17 C3 122.8(2) . . ?
C4 C9 N1 110.1(2) . . ?
C8 C9 N1 128.9(2) . . ?
C8 C9 C4 121.0(2) . . ?
O33 N31 O32 123.9(3) . . ?
O33 N31 C26 118.3(3) . . ?
O32 N31 C26 117.7(3) . . ?
C9 C4 C3 108.1(2) . . ?
C5 C4 C9 121.3(2) . . ?
C5 C4 C3 130.6(2) . . ?
C25 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C29 C30 C25 121.6(2) . . ?
O36 C2 N1 126.4(2) . . ?
O36 C2 C3 126.1(2) . . ?
N1 C2 C3 107.4(2) . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.1(2) . . ?
C6 C5 H5 121.0 . . ?
C9 C8 H8 121.1 . . ?
C7 C8 C9 117.8(2) . . ?
C7 C8 H8 121.1 . . ?
C30 C25 C24 119.7(2) . . ?
C26 C25 C30 116.3(2) . . ?
C26 C25 C24 123.9(2) . . ?
N17 C3 C4 116.4(2) . . ?
N17 C3 C2 113.95(19) . . ?
N17 C3 C24 108.89(19) . . ?
C4 C3 C2 101.99(18) . . ?
C4 C3 C24 110.59(19) . . ?
C24 C3 C2 104.28(19) . . ?
O34 C6 C5 124.2(2) . . ?
O34 C6 C7 115.8(2) . . ?
C5 C6 C7 120.0(2) . . ?
C25 C24 C3 113.8(2) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C3 C24 H24A 108.8 . . ?
C3 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C30 C29 H29 119.9 . . ?
C28 C29 C30 120.3(2) . . ?
C28 C29 H29 119.9 . . ?
C16 C11 C10 120.2(2) . . ?
C12 C11 C16 118.4(2) . . ?
C12 C11 C10 121.4(2) . . ?
C11 C16 H16 119.8 . . ?
C11 C16 C15 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
N17 C18 C19 117.1(3) . . ?
C23 C18 N17 124.7(2) . . ?
C23 C18 C19 118.2(3) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
N1 C10 C11 112.4(2) . . ?
N1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C29 C28 H28 119.9 . . ?
C29 C28 C27 120.3(3) . . ?
C27 C28 H28 119.9 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.4(2) . . ?
C13 C12 H12 119.3 . . ?
C25 C26 N31 122.3(2) . . ?
C27 C26 N31 114.8(2) . . ?
C27 C26 C25 122.9(2) . . ?
C8 C7 C6 121.8(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C28 C27 C26 118.7(2) . . ?
C28 C27 H27 120.6 . . ?
C26 C27 H27 120.6 . . ?
O34 C35 H35A 109.5 . . ?
O34 C35 H35B 109.5 . . ?
O34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C23 C22 H22 119.2 . . ?
C23 C22 C21 121.5(3) . . ?
C21 C22 H22 119.2 . . ?
C22 C21 H21 121.1 . . ?
C22 C21 C20 117.9(3) . . ?
C20 C21 H21 121.1 . . ?
C19 C20 C21 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 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
O36 C2 C3 N17 -48.7(3) . . . . ?
O36 C2 C3 C4 -174.9(2) . . . . ?
O36 C2 C3 C24 69.9(3) . . . . ?
O34 C6 C7 C8 179.9(2) . . . . ?
N1 C9 C4 C5 -177.3(2) . . . . ?
N1 C9 C4 C3 5.5(3) . . . . ?
N1 C9 C8 C7 178.0(2) . . . . ?
N1 C2 C3 N17 135.0(2) . . . . ?
N1 C2 C3 C4 8.7(2) . . . . ?
N1 C2 C3 C24 -106.4(2) . . . . ?
N17 C3 C24 C25 -77.6(2) . . . . ?
N17 C18 C23 C22 -178.0(2) . . . . ?
N17 C18 C19 C20 178.6(3) . . . . ?
O33 N31 C26 C25 -44.3(4) . . . . ?
O33 N31 C26 C27 133.5(3) . . . . ?
O32 N31 C26 C25 138.3(3) . . . . ?
O32 N31 C26 C27 -43.9(4) . . . . ?
C9 N1 C2 O36 177.7(2) . . . . ?
C9 N1 C2 C3 -6.0(3) . . . . ?
C9 N1 C10 C11 65.1(3) . . . . ?
C9 C4 C5 C6 -1.4(4) . . . . ?
C9 C4 C3 N17 -133.1(2) . . . . ?
C9 C4 C3 C2 -8.5(2) . . . . ?
C9 C4 C3 C24 102.0(2) . . . . ?
C9 C8 C7 C6 -1.0(4) . . . . ?
N31 C26 C27 C28 -177.0(3) . . . . ?
C4 C9 C8 C7 0.8(4) . . . . ?
C4 C5 C6 O34 -178.7(2) . . . . ?
C4 C5 C6 C7 1.2(4) . . . . ?
C4 C3 C24 C25 51.5(2) . . . . ?
C30 C25 C24 C3 78.0(3) . . . . ?
C30 C25 C26 N31 177.4(3) . . . . ?
C30 C25 C26 C27 -0.2(4) . . . . ?
C30 C29 C28 C27 0.3(4) . . . . ?
C2 N1 C9 C4 0.4(3) . . . . ?
C2 N1 C9 C8 -177.0(3) . . . . ?
C2 N1 C10 C11 -110.6(3) . . . . ?
C2 C3 C24 C25 160.43(18) . . . . ?
C5 C4 C3 N17 50.0(4) . . . . ?
C5 C4 C3 C2 174.7(2) . . . . ?
C5 C4 C3 C24 -74.9(3) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C8 C9 C4 C5 0.4(4) . . . . ?
C8 C9 C4 C3 -176.8(2) . . . . ?
C25 C30 C29 C28 0.3(4) . . . . ?
C25 C26 C27 C28 0.8(4) . . . . ?
C3 N17 C18 C23 -21.8(4) . . . . ?
C3 N17 C18 C19 159.5(2) . . . . ?
C3 C4 C5 C6 175.1(2) . . . . ?
C24 C25 C26 N31 -7.4(4) . . . . ?
C24 C25 C26 C27 175.0(3) . . . . ?
C29 C30 C25 C24 -175.8(2) . . . . ?
C29 C30 C25 C26 -0.4(4) . . . . ?
C29 C28 C27 C26 -0.8(4) . . . . ?
C11 C16 C15 C14 -1.0(4) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C16 C11 C10 N1 -141.2(2) . . . . ?
C16 C11 C12 C13 1.1(4) . . . . ?
C16 C15 C14 C13 0.9(4) . . . . ?
C18 N17 C3 C4 64.7(3) . . . . ?
C18 N17 C3 C2 -53.6(3) . . . . ?
C18 N17 C3 C24 -169.6(2) . . . . ?
C18 C23 C22 C21 -0.8(4) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C23 C18 C19 C20 -0.2(4) . . . . ?
C23 C22 C21 C20 0.3(5) . . . . ?
C15 C14 C13 C12 0.1(5) . . . . ?
C10 N1 C9 C4 -175.7(2) . . . . ?
C10 N1 C9 C8 6.9(4) . . . . ?
C10 N1 C2 O36 -6.2(4) . . . . ?
C10 N1 C2 C3 170.1(2) . . . . ?
C10 C11 C16 C15 -178.8(2) . . . . ?
C10 C11 C12 C13 179.9(3) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
C12 C11 C10 N1 40.0(3) . . . . ?
C26 C25 C24 C3 -97.1(3) . . . . ?
C35 O34 C6 C5 -13.2(4) . . . . ?
C35 O34 C6 C7 166.9(2) . . . . ?
C19 C18 C23 C22 0.7(4) . . . . ?
C22 C21 C20 C19 0.2(5) . . . . ?

_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 3.003
_oxdiff_exptl_absorpt_empirical_full_min 0.287
####################################################################### 
# 
# 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_hanx_210727_auto
_database_code_depnum_ccdc_archive 'CCDC 2122358'
loop_
_audit_author_name
_audit_author_address
HANXIAO
;SYSU data center
China
;
_audit_update_record             
;
2021-11-16 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-07-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F N4 O3'
_chemical_formula_sum            'C23 H19 F N4 O3'
_chemical_formula_weight         418.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   11.22990(10)
_cell_length_b                   7.59620(10)
_cell_length_c                   11.50980(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.8060(10)
_cell_angle_gamma                90
_cell_volume                     981.351(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17155
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.8690
_cell_measurement_theta_min      3.8230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
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    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19231
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.196
_diffrn_reflns_theta_min         3.842
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  62.00   0.50    0.05    --  105.51 -61.00-180.00   60
  2  ω      2.00  33.00   0.50    0.05    --   45.81 -28.00 -93.00   62
  3  ω     56.00 118.00   0.50    0.05    --   45.81  28.00  68.00  124
  4  ω     33.00  73.00   0.50    0.05    --  105.51 -61.00 120.00   80
  5  ω    109.00 134.00   0.50    0.05    --  105.51  28.00  68.00   50
  6  ω     34.00  73.00   0.50    0.05    --  105.51 -61.00 -60.00   78
  7  ω     39.00  69.00   0.50    0.05    --  105.51 -61.00 -90.00   60
  8  ω     34.00  70.00   0.50    0.05    --  105.51 -61.00 -30.00   72
  9  ω     32.00  69.00   0.50    0.05    --  105.51 -61.00  30.00   74
 10  ω     36.00  69.00   0.50    0.05    --  105.51 -61.00  60.00   66
 11  ω     34.00  70.00   0.50    0.05    --  105.51 -61.00  90.00   72
 12  ω     46.00  72.00   0.50    0.05    --  105.51 -61.00 150.00   52
 13  ω     34.00  84.00   0.50    0.05    --  105.51-125.00 150.00  100
 14  ω    -20.00  29.00   0.50    0.05    --  -45.81  28.00  68.00   98
 15  ω     -6.00  29.00   0.50    0.05    --  -45.81  19.00-150.00   70
 16  ω    -23.00  31.00   0.50    0.05    --  -45.81  19.00-180.00  108
 17  ω     72.00  97.00   0.50    0.05    --  105.51 -94.00 -30.00   50
 18  ω    -52.00 -27.00   0.50    0.05    -- -100.00  77.00  30.00   50
 19  ω    -54.00 -27.00   0.50    0.05    -- -100.00  61.00  60.00   54
 20  ω    -98.00 -72.00   0.50    0.05    -- -100.00  77.00  30.00   52
 21  ω   -112.00 -64.00   0.50    0.05    -- -100.00 125.00 150.00   96
 22  ω    -54.00 -29.00   0.50    0.05    -- -100.00 125.00 150.00   50
 23  ω   -121.00 -53.00   0.50    0.05    --  -45.81 -28.00 -93.00  136
 24  ω   -175.00 -83.00   0.50    0.05    -- -100.00 -28.00 -93.00  184
 25  ω     99.00 161.00   0.50    0.05    --  112.25  28.00  68.00  124
 26  ω    -62.00 -29.00   0.50    0.05    --  -45.56 -50.00-150.66   66
 27  ω    -20.00  20.00   0.50    0.05    --  -45.56  19.00   0.00   80
 28  ω     83.00 109.00   0.50    0.05    --   45.56  77.00 120.00   52
 29  ω     23.00  69.00   0.50    0.05    --   45.56  77.00 120.00   92
 30  ω     27.00  74.00   0.50    0.05    --   45.56  77.00-180.00   94
 31  ω   -155.00-129.00   0.50    0.05    -- -100.00 -64.00-120.44   52
 32  ω   -100.00 -75.00   0.50    0.05    -- -100.00 -77.00 150.00   50
 33  ω   -115.00 -82.00   0.50    0.05    -- -100.00 -64.00-120.44   66
 34  ω   -102.00 -76.00   0.50    0.05    -- -100.00 -74.00 104.31   52
 35  ω   -104.00 -75.00   0.50    0.05    -- -100.00 -77.00-120.00   58
 36  ω   -143.00-115.00   0.50    0.05    -- -100.00 -61.00-150.00   56
 37  ω   -173.00-117.00   0.50    0.05    -- -100.00 -77.00-150.00  112
 38  ω   -104.00 -75.00   0.50    0.05    -- -100.00 -77.00-180.00   58
 39  ω   -122.00 -79.00   0.50    0.05    -- -100.00 -66.00-154.60   86
 40  ω   -102.00 -77.00   0.50    0.05    -- -100.00 -71.00 126.60   50
 41  ω   -104.00 -78.00   0.50    0.05    -- -100.00 -70.00-174.96   52
 42  ω   -108.00 -81.00   0.50    0.05    -- -100.00 -65.00 126.29   54
 43  ω   -171.00-123.00   0.50    0.05    -- -100.00 -77.00 120.00   96
 44  ω    -69.00 -44.00   0.50    0.05    -- -100.00  61.00-150.00   50
 45  ω   -106.00 -80.00   0.50    0.05    -- -100.00 -77.00 120.00   52
 46  ω   -167.00-141.00   0.50    0.05    -- -100.00 -77.00 150.00   52
 47  ω   -167.00-141.00   0.50    0.05    -- -100.00 -54.00-174.13   52
 48  ω   -132.00 -82.00   0.50    0.05    -- -100.00 -61.00 150.00  100
 49  ω   -110.00 -81.00   0.50    0.05    -- -100.00 -61.00-150.00   58
 50  ω   -101.00 -75.00   0.50    0.05    -- -100.00 -77.00 126.65   52
 51  ω    -65.00 -28.00   0.50    0.05    -- -100.00  61.00 -30.00   74
 52  ω   -163.00-138.00   0.50    0.05    -- -100.00 -61.00-180.00   50
 53  ω   -129.00 -82.00   0.50    0.05    -- -100.00 -61.00-180.00   94
 54  ω   -140.00 -84.00   0.50    0.05    -- -100.00 -53.00 159.79  112
 55  ω   -109.00 -83.00   0.50    0.05    -- -100.00 -43.00  99.53   52
 56  ω   -100.00 -75.00   0.50    0.05    -- -100.00 -77.00-150.00   50
 57  ω   -126.00 -78.00   0.50    0.05    -- -100.00 -76.00-154.04   96
 58  ω   -123.00 -79.00   0.50    0.05    -- -100.00 -68.00 144.54   88
 59  ω   -112.00 -82.00   0.50    0.05    -- -100.00 -54.00-174.13   60
 60  ω     60.00  93.00   0.50    0.05    --  112.25 -94.00  90.00   66
 61  ω     65.00  91.00   0.50    0.05    --  112.25 -94.00 -30.00   52
 62  ω     48.00 102.00   0.50    0.05    --  112.25-125.00-180.00  108
 63  ω    130.00 175.00   0.50    0.05    --  112.25 125.00-180.00   90
 64  ω     89.00 114.00   0.50    0.05    --  112.25 125.00-180.00   50
 65  ω     64.00  97.00   0.50    0.05    --  112.25 -77.00 -90.00   66
 66  ω     97.00 161.00   0.50    0.05    --  112.25  77.00  90.00  128
 67  ω     94.00 146.00   0.50    0.05    --  112.25  61.00   0.00  104
 68  ω   -118.00 -21.00   0.50    0.05    --  -45.56 -77.00-150.00  194
 69  ω   -118.00 -21.00   0.50    0.05    --  -45.56 -77.00   0.00  194
 70  ω    -95.00 -14.00   0.50    0.05    --  -45.56 125.00-150.00  162
 71  ω     18.00  95.00   0.50    0.05    --   45.56-125.00  60.00  154
 72  ω     28.00 118.00   0.50    0.05    --   45.56  57.00  90.00  180
 73  ω     21.00 118.00   0.50    0.05    --   45.56  77.00 -30.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0164459000
_diffrn_orient_matrix_UB_12      0.0710531000
_diffrn_orient_matrix_UB_13      0.1247597000
_diffrn_orient_matrix_UB_21      -0.1351120000
_diffrn_orient_matrix_UB_22      -0.0160226000
_diffrn_orient_matrix_UB_23      0.0168212000
_diffrn_orient_matrix_UB_31      0.0176043000
_diffrn_orient_matrix_UB_32      -0.1894338000
_diffrn_orient_matrix_UB_33      0.0454027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.889
_reflns_number_gt                3845
_reflns_number_total             3917
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1664 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       0.0067(9)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.045
_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)+(0.0457P)²+0.2076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C24(H24), C21(H21), C14(H14), C5(H5), C18(H18),
 C22(H22), C23(H23), C17(H17), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_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
F31 F 0.83373(12) 0.1235(2) 0.07472(11) 0.0347(3) Uani 1 1 d . . . . .
O29 O 0.63892(13) 0.29431(19) 0.61123(12) 0.0235(3) Uani 1 1 d . . . . .
O28 O 0.42053(14) 0.4539(2) 0.71642(14) 0.0336(4) Uani 1 1 d . . . . .
O27 O 0.53171(16) 0.3403(2) 0.85368(14) 0.0349(4) Uani 1 1 d . . . . .
N8 N 0.81049(15) 0.4589(2) 0.64078(14) 0.0215(4) Uani 1 1 d . . . . .
N26 N 0.50282(16) 0.4621(3) 0.78780(15) 0.0260(4) Uani 1 1 d . . . . .
N7 N 0.62099(16) 0.5408(2) 0.40237(14) 0.0227(4) Uani 1 1 d . . . . .
H7 H 0.592381 0.636693 0.368895 0.027 Uiso 1 1 d R U . . .
N9 N 0.86451(15) 0.6113(2) 0.59311(14) 0.0231(4) Uani 1 1 d . . . . .
C12 C 0.70072(18) 0.4227(3) 0.59223(16) 0.0206(4) Uani 1 1 d . . . . .
C3 C 0.82897(19) 0.2229(3) 0.26872(18) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.893065 0.146612 0.289889 0.030 Uiso 1 1 calc R U . . .
C2 C 0.77780(18) 0.3307(3) 0.35111(17) 0.0239(4) Uani 1 1 d . . . . .
H2 H 0.807924 0.328497 0.429159 0.029 Uiso 1 1 calc R U . . .
C1 C 0.68291(18) 0.4419(3) 0.32096(17) 0.0216(4) Uani 1 1 d . . . . .
C13 C 0.88201(18) 0.3456(3) 0.71306(17) 0.0224(4) Uani 1 1 d . . . . .
C4 C 0.7850(2) 0.2292(3) 0.15627(19) 0.0260(4) Uani 1 1 d . . . . .
C10 C 0.78776(18) 0.6795(3) 0.52105(17) 0.0219(4) Uani 1 1 d . . . . .
C6 C 0.64301(19) 0.4475(3) 0.20475(17) 0.0250(4) Uani 1 1 d . . . . .
H6 H 0.580661 0.526008 0.181987 0.030 Uiso 1 1 calc R U . . .
C20 C 0.59926(18) 0.7327(3) 0.70496(17) 0.0226(4) Uani 1 1 d . . . . .
C25 C 0.57096(18) 0.6277(3) 0.80030(17) 0.0237(4) Uani 1 1 d . . . . .
C24 C 0.59988(19) 0.6751(3) 0.91442(18) 0.0277(5) Uani 1 1 d . . . . .
H24 H 0.578601 0.600888 0.976890 0.033 Uiso 1 1 calc R U . . .
C19 C 0.57111(18) 0.6886(3) 0.57887(17) 0.0233(4) Uani 1 1 d . . . . .
H19A H 0.556464 0.799838 0.535893 0.028 Uiso 1 1 calc R U . . .
H19B H 0.496402 0.619432 0.574532 0.028 Uiso 1 1 calc R U . . .
C21 C 0.65890(19) 0.8892(3) 0.73115(19) 0.0258(5) Uani 1 1 d . . . . .
H21 H 0.679845 0.964522 0.669159 0.031 Uiso 1 1 calc R U . . .
C14 C 0.89897(19) 0.1732(3) 0.6781(2) 0.0284(5) Uani 1 1 d . . . . .
H14 H 0.863010 0.131599 0.607557 0.034 Uiso 1 1 calc R U . . .
C11 C 0.66952(18) 0.5835(3) 0.51659(17) 0.0214(4) Uani 1 1 d . . . . .
C5 C 0.6934(2) 0.3399(3) 0.12232(18) 0.0270(5) Uani 1 1 d . . . . .
H5 H 0.665114 0.342631 0.043675 0.032 Uiso 1 1 calc R U . . .
C18 C 0.9340(2) 0.4093(3) 0.81563(19) 0.0287(5) Uani 1 1 d . . . . .
H18 H 0.920865 0.527170 0.839587 0.034 Uiso 1 1 calc R U . . .
C30 C 0.8161(2) 0.8346(3) 0.44772(18) 0.0270(4) Uani 1 1 d . . . . .
H30A H 0.895599 0.878804 0.469744 0.040 Uiso 1 1 calc R U . . .
H30B H 0.757004 0.927396 0.459442 0.040 Uiso 1 1 calc R U . . .
H30C H 0.814213 0.799705 0.365713 0.040 Uiso 1 1 calc R U . . .
C22 C 0.6890(2) 0.9394(3) 0.84434(19) 0.0301(5) Uani 1 1 d . . . . .
H22 H 0.729300 1.047535 0.858748 0.036 Uiso 1 1 calc R U . . .
C23 C 0.6599(2) 0.8313(3) 0.93617(19) 0.0309(5) Uani 1 1 d . . . . .
H23 H 0.681144 0.864223 1.013710 0.037 Uiso 1 1 calc R U . . .
C17 C 1.0058(2) 0.2966(4) 0.8827(2) 0.0347(5) Uani 1 1 d . . . . .
H17 H 1.043235 0.338723 0.952495 0.042 Uiso 1 1 calc R U . . .
C16 C 1.0232(2) 0.1241(4) 0.8489(2) 0.0357(5) Uani 1 1 d . . . . .
H16 H 1.072234 0.048354 0.895309 0.043 Uiso 1 1 calc R U . . .
C15 C 0.9689(2) 0.0618(3) 0.7472(2) 0.0350(5) Uani 1 1 d . . . . .
H15 H 0.979704 -0.057275 0.724648 0.042 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
F31 C4 1.363(2) . ?
O29 C12 1.221(3) . ?
O28 N26 1.219(2) . ?
O27 N26 1.233(3) . ?
N8 N9 1.425(2) . ?
N8 C12 1.365(3) . ?
N8 C13 1.427(3) . ?
N26 C25 1.477(3) . ?
N7 H7 0.8799 . ?
N7 C1 1.403(3) . ?
N7 C11 1.444(3) . ?
N9 C10 1.286(3) . ?
C12 C11 1.534(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.390(3) . ?
C3 C4 1.372(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.395(3) . ?
C1 C6 1.398(3) . ?
C13 C14 1.385(3) . ?
C13 C18 1.387(3) . ?
C4 C5 1.376(3) . ?
C10 C11 1.515(3) . ?
C10 C30 1.489(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(3) . ?
C20 C25 1.401(3) . ?
C20 C19 1.513(3) . ?
C20 C21 1.393(3) . ?
C25 C24 1.390(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.384(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C11 1.557(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.393(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.382(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.386(4) . ?
C15 H15 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
N9 N8 C13 118.41(16) . . ?
C12 N8 N9 113.33(16) . . ?
C12 N8 C13 126.99(18) . . ?
O28 N26 O27 123.8(2) . . ?
O28 N26 C25 119.24(18) . . ?
O27 N26 C25 116.96(17) . . ?
C1 N7 H7 109.4 . . ?
C1 N7 C11 123.20(17) . . ?
C11 N7 H7 109.6 . . ?
C10 N9 N8 106.92(16) . . ?
O29 C12 N8 126.78(19) . . ?
O29 C12 C11 128.08(18) . . ?
N8 C12 C11 105.01(17) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C4 C3 C2 118.6(2) . . ?
C3 C2 H2 119.5 . . ?
C3 C2 C1 121.04(19) . . ?
C1 C2 H2 119.5 . . ?
C2 C1 N7 123.30(18) . . ?
C2 C1 C6 118.42(18) . . ?
C6 C1 N7 118.18(18) . . ?
C14 C13 N8 118.75(19) . . ?
C14 C13 C18 121.2(2) . . ?
C18 C13 N8 120.0(2) . . ?
F31 C4 C3 119.3(2) . . ?
F31 C4 C5 118.52(19) . . ?
C3 C4 C5 122.2(2) . . ?
N9 C10 C11 113.36(18) . . ?
N9 C10 C30 122.25(19) . . ?
C30 C10 C11 124.36(18) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C25 C20 C19 125.4(2) . . ?
C21 C20 C25 115.84(19) . . ?
C21 C20 C19 118.75(19) . . ?
C20 C25 N26 122.56(18) . . ?
C24 C25 N26 114.68(18) . . ?
C24 C25 C20 122.7(2) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 C25 119.4(2) . . ?
C23 C24 H24 120.3 . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C20 C19 C11 115.17(16) . . ?
H19A C19 H19B 107.5 . . ?
C11 C19 H19A 108.5 . . ?
C11 C19 H19B 108.5 . . ?
C20 C21 H21 118.7 . . ?
C22 C21 C20 122.6(2) . . ?
C22 C21 H21 118.7 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
N7 C11 C12 114.27(17) . . ?
N7 C11 C10 116.38(16) . . ?
N7 C11 C19 106.34(16) . . ?
C12 C11 C19 107.46(16) . . ?
C10 C11 C12 100.38(16) . . ?
C10 C11 C19 111.80(17) . . ?
C4 C5 C6 118.93(19) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C13 C18 H18 120.7 . . ?
C13 C18 C17 118.6(2) . . ?
C17 C18 H18 120.7 . . ?
C10 C30 H30A 109.5 . . ?
C10 C30 H30B 109.5 . . ?
C10 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.7 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?

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
F31 C4 C5 C6 179.8(2) . . . . ?
O29 C12 C11 N7 -49.1(3) . . . . ?
O29 C12 C11 C10 -174.40(19) . . . . ?
O29 C12 C11 C19 68.6(3) . . . . ?
O28 N26 C25 C20 -38.4(3) . . . . ?
O28 N26 C25 C24 138.7(2) . . . . ?
O27 N26 C25 C20 143.4(2) . . . . ?
O27 N26 C25 C24 -39.5(3) . . . . ?
N8 N9 C10 C11 2.8(2) . . . . ?
N8 N9 C10 C30 -175.52(18) . . . . ?
N8 C12 C11 N7 134.88(17) . . . . ?
N8 C12 C11 C10 9.57(19) . . . . ?
N8 C12 C11 C19 -107.39(18) . . . . ?
N8 C13 C14 C15 179.6(2) . . . . ?
N8 C13 C18 C17 -178.4(2) . . . . ?
N26 C25 C24 C23 -177.68(19) . . . . ?
N7 C1 C6 C5 -173.8(2) . . . . ?
N9 N8 C12 O29 174.72(18) . . . . ?
N9 N8 C12 C11 -9.2(2) . . . . ?
N9 N8 C13 C14 -118.1(2) . . . . ?
N9 N8 C13 C18 61.3(3) . . . . ?
N9 C10 C11 N7 -131.64(19) . . . . ?
N9 C10 C11 C12 -7.8(2) . . . . ?
N9 C10 C11 C19 105.9(2) . . . . ?
C12 N8 N9 C10 4.4(2) . . . . ?
C12 N8 C13 C14 48.1(3) . . . . ?
C12 N8 C13 C18 -132.6(2) . . . . ?
C3 C2 C1 N7 173.9(2) . . . . ?
C3 C2 C1 C6 -2.3(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C2 C3 C4 F31 -179.58(19) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
C1 N7 C11 C12 -60.0(3) . . . . ?
C1 N7 C11 C10 56.4(3) . . . . ?
C1 N7 C11 C19 -178.35(18) . . . . ?
C1 C6 C5 C4 -1.1(3) . . . . ?
C13 N8 N9 C10 172.42(17) . . . . ?
C13 N8 C12 O29 7.9(3) . . . . ?
C13 N8 C12 C11 -175.96(18) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C13 C18 C17 C16 -1.1(4) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C20 C25 C24 C23 -0.5(3) . . . . ?
C20 C19 C11 N7 174.65(18) . . . . ?
C20 C19 C11 C12 51.9(2) . . . . ?
C20 C19 C11 C10 -57.3(2) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C25 C20 C19 C11 -90.3(2) . . . . ?
C25 C20 C21 C22 0.0(3) . . . . ?
C25 C24 C23 C22 0.9(3) . . . . ?
C19 C20 C25 N26 -3.4(3) . . . . ?
C19 C20 C25 C24 179.6(2) . . . . ?
C19 C20 C21 C22 -179.6(2) . . . . ?
C21 C20 C25 N26 177.00(19) . . . . ?
C21 C20 C25 C24 0.1(3) . . . . ?
C21 C20 C19 C11 89.3(2) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C11 N7 C1 C2 20.6(3) . . . . ?
C11 N7 C1 C6 -163.21(19) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C18 C17 C16 C15 0.1(4) . . . . ?
C30 C10 C11 N7 46.6(3) . . . . ?
C30 C10 C11 C12 170.46(18) . . . . ?
C30 C10 C11 C19 -75.9(2) . . . . ?
C17 C16 C15 C14 1.2(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 2.570
_oxdiff_exptl_absorpt_empirical_full_min 0.552
