# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_202209186
_database_code_depnum_ccdc_archive 'CCDC 2219965'
loop_
_audit_author_name
_audit_author_address
A
;Chongqing Medical University
China
;
_audit_update_record             
;
2022-11-16 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 F N2 O5'
_chemical_formula_sum            'C18 H15 F N2 O5'
_chemical_formula_weight         358.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2F1
_chemical_oxdiff_usercomment     r
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.98207(19)
_cell_length_b                   13.3543(3)
_cell_length_c                   29.0314(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3482.30(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8720
_cell_measurement_theta_min      4.4870
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13419
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.862
_diffrn_reflns_theta_min         4.499
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00  55.00   0.50    1.00    --    0.00  57.00 -30.00   54
  2  ω   -106.00 -34.00   0.50    1.90    --  -33.50 178.00-120.00  144
  3  ω     61.00  88.00   0.50    1.90    --   36.47  77.00 -90.00   54
  4  ω     62.00 109.00   0.50    1.90    --   36.47 178.00 -90.00   94
  5  ω     62.00  98.00   0.50    1.90    --   36.47-151.00 -57.00   72
  6  ω     17.00  76.00   0.50    1.90    --   36.47  37.00  30.00  118
  7  ω      7.00  38.00   0.50    1.90    --   36.47 -77.00-120.00   62
  8  ω     19.00  98.00   0.50    1.90    --   36.47  57.00  60.00  158
  9  ω      9.00  58.00   0.50    1.90    --   36.47  77.00 -90.00   98
 10  ω     72.00 107.00   0.50   10.00    --  108.00 -94.00-150.00   70
 11  ω     38.00 114.00   0.50   10.00    --  108.00 -45.00-180.00  152
 12  ω     37.00 150.00   0.50   10.00    --  108.00 -15.00 150.00  226
 13  ω     44.00 119.00   0.50   10.00    --  108.00 -61.00 -90.00  150
 14  ω     37.00 133.00   0.50   10.00    --  108.00 -30.00 -90.00  192
 15  ω     69.00 107.00   0.50   10.00    --  108.00 -94.00 120.00   76
 16  ω     78.00 111.00   0.50   10.00    --  108.00-111.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0957683000
_diffrn_orient_matrix_UB_12      -0.0929356000
_diffrn_orient_matrix_UB_13      -0.0103436000
_diffrn_orient_matrix_UB_21      0.1391569000
_diffrn_orient_matrix_UB_22      0.0669440000
_diffrn_orient_matrix_UB_23      -0.0039269000
_diffrn_orient_matrix_UB_31      0.0297304000
_diffrn_orient_matrix_UB_32      -0.0134389000
_diffrn_orient_matrix_UB_33      0.0519156000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                5430
_reflns_number_total             6579
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         6579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.043
_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)+(0.0576P)²+0.1302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1288
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C9'(H9')
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10'(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C15(H15), C16(H16),
 C1'(H1'A), C2'(H2'), C3'(H3'), C4'(H4'), C12'(H12'), C13'(H13'), C15'(H15'),
 C16'(H16')
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18'(H18D,H18E,H18F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.2839(3) 0.4654(5) 0.75387(13) 0.160(2) Uani 1 1 d . . . . .
O1 O 0.6872(3) 0.6455(2) 0.63088(10) 0.0708(7) Uani 1 1 d . . . . .
O2 O 0.6954(6) 0.6967(4) 0.79368(15) 0.1299(17) Uani 1 1 d . . . . .
O3 O 0.5672(5) 0.5693(3) 0.80837(11) 0.0998(12) Uani 1 1 d . . . . .
O4 O 0.4757(3) 0.4843(2) 0.66461(8) 0.0542(6) Uani 1 1 d . . . . .
O5 O 0.4811(3) 0.4824(3) 0.58748(9) 0.0771(9) Uani 1 1 d . . . . .
N1 N 0.8203(3) 0.5051(2) 0.61077(10) 0.0557(7) Uani 1 1 d . . . . .
H1 H 0.875(5) 0.533(3) 0.5893(15) 0.064(12) Uiso 1 1 d . . . . .
N2 N 0.6249(4) 0.6250(3) 0.78155(13) 0.0727(10) Uani 1 1 d . . . . .
C1 C 0.6593(5) 0.2872(3) 0.66217(15) 0.0663(10) Uani 1 1 d . . . . .
H1A H 0.5856 0.2744 0.6839 0.080 Uiso 1 1 calc R . . . .
C2 C 0.7348(6) 0.2089(3) 0.64014(19) 0.0823(13) Uani 1 1 d . . . . .
H2 H 0.7103 0.1429 0.6470 0.099 Uiso 1 1 calc R . . . .
C3 C 0.8454(6) 0.2286(4) 0.60833(18) 0.0827(13) Uani 1 1 d . . . . .
H3 H 0.8949 0.1756 0.5943 0.099 Uiso 1 1 calc R . . . .
C4 C 0.8838(5) 0.3251(4) 0.59696(14) 0.0702(11) Uani 1 1 d . . . . .
H4 H 0.9584 0.3379 0.5756 0.084 Uiso 1 1 calc R . . . .
C5 C 0.8088(4) 0.4018(3) 0.61809(11) 0.0532(7) Uani 1 1 d . . . . .
C6 C 0.6979(4) 0.3835(3) 0.65058(11) 0.0499(7) Uani 1 1 d . . . . .
C7 C 0.6361(4) 0.4817(3) 0.66660(11) 0.0491(7) Uani 1 1 d . . . . .
C8 C 0.7133(4) 0.5575(3) 0.63391(11) 0.0537(8) Uani 1 1 d . . . . .
C9 C 0.6715(4) 0.5054(3) 0.71798(10) 0.0482(7) Uani 1 1 d . . . . .
H9 H 0.6212 0.4545 0.7366 0.058 Uiso 1 1 calc R . . . .
C10 C 0.6046(5) 0.6065(3) 0.73123(12) 0.0618(9) Uani 1 1 d . . . . .
H10A H 0.6527 0.6593 0.7138 0.074 Uiso 1 1 calc R . . . .
H10B H 0.4993 0.6072 0.7238 0.074 Uiso 1 1 calc R . . . .
C11 C 0.8374(4) 0.4969(3) 0.72805(11) 0.0550(8) Uani 1 1 d . . . . .
C12 C 0.9343(5) 0.5756(4) 0.72181(15) 0.0744(11) Uani 1 1 d . . . . .
H12 H 0.8987 0.6369 0.7113 0.089 Uiso 1 1 calc R . . . .
C13 C 1.0863(6) 0.5637(6) 0.73120(17) 0.0975(19) Uani 1 1 d . . . . .
H13 H 1.1514 0.6173 0.7275 0.117 Uiso 1 1 calc R . . . .
C14 C 1.1366(5) 0.4762(7) 0.74534(17) 0.103(2) Uani 1 1 d . . . . .
C15 C 1.0474(6) 0.3955(5) 0.75123(17) 0.0956(18) Uani 1 1 d . . . . .
H15 H 1.0867 0.3342 0.7604 0.115 Uiso 1 1 calc R . . . .
C16 C 0.8944(5) 0.4065(4) 0.74323(14) 0.0705(11) Uani 1 1 d . . . . .
H16 H 0.8308 0.3526 0.7482 0.085 Uiso 1 1 calc R . . . .
C17 C 0.4118(4) 0.4780(3) 0.62289(12) 0.0631(10) Uani 1 1 d . . . . .
C18 C 0.2478(5) 0.4610(5) 0.62675(15) 0.0859(15) Uani 1 1 d . . . . .
H18A H 0.2297 0.3999 0.6432 0.129 Uiso 1 1 calc GR . . . .
H18B H 0.2053 0.4565 0.5965 0.129 Uiso 1 1 calc GR . . . .
H18C H 0.2032 0.5159 0.6431 0.129 Uiso 1 1 calc GR . . . .
F1' F 0.2403(3) 0.5826(4) 0.36080(12) 0.1233(14) Uani 1 1 d . . . . .
O1' O 0.8099(4) 0.7007(2) 0.50075(11) 0.0826(9) Uani 1 1 d . . . . .
O2' O 0.8227(5) 0.8123(3) 0.34199(17) 0.1222(16) Uani 1 1 d . . . . .
O3' O 0.9321(6) 0.6830(4) 0.31582(13) 0.1159(16) Uani 1 1 d . . . . .
O4' O 1.0447(3) 0.5698(2) 0.45683(8) 0.0589(6) Uani 1 1 d . . . . .
O5' O 1.0331(3) 0.5269(3) 0.53115(9) 0.0750(9) Uani 1 1 d . . . . .
N1' N 0.6951(3) 0.5476(3) 0.50684(10) 0.0599(7) Uani 1 1 d . . . . .
H1' H 0.631(5) 0.565(3) 0.5301(15) 0.066(12) Uiso 1 1 d . . . . .
N2' N 0.8888(5) 0.7347(3) 0.34688(16) 0.0815(12) Uani 1 1 d . . . . .
C1' C 0.8790(5) 0.3656(3) 0.43652(14) 0.0678(10) Uani 1 1 d . . . . .
H1'A H 0.9555 0.3659 0.4150 0.081 Uiso 1 1 calc R . . . .
C2' C 0.8069(7) 0.2766(3) 0.44861(17) 0.0859(14) Uani 1 1 d . . . . .
H2' H 0.8361 0.2166 0.4351 0.103 Uiso 1 1 calc R . . . .
C3' C 0.6929(6) 0.2772(4) 0.48047(16) 0.0848(14) Uani 1 1 d . . . . .
H3' H 0.6464 0.2171 0.4881 0.102 Uiso 1 1 calc R . . . .
C4' C 0.6461(5) 0.3640(4) 0.50125(14) 0.0722(11) Uani 1 1 d . . . . .
H4' H 0.5683 0.3641 0.5224 0.087 Uiso 1 1 calc R . . . .
C5' C 0.7191(4) 0.4506(3) 0.48955(11) 0.0554(8) Uani 1 1 d . . . . .
C6' C 0.8336(4) 0.4523(3) 0.45734(11) 0.0499(7) Uani 1 1 d . . . . .
C7' C 0.8851(4) 0.5581(3) 0.45181(11) 0.0490(7) Uani 1 1 d . . . . .
C8' C 0.7952(4) 0.6139(3) 0.48993(12) 0.0583(8) Uani 1 1 d . . . . .
C9' C 0.8513(4) 0.5991(3) 0.40285(11) 0.0521(7) Uani 1 1 d . . . . .
H9' H 0.8986 0.5534 0.3809 0.062 Uiso 1 1 calc R . . . .
C10' C 0.9211(5) 0.7017(3) 0.39552(15) 0.0669(10) Uani 1 1 d . . . . .
H10C H 0.8797 0.7494 0.4172 0.080 Uiso 1 1 calc R . . . .
H10D H 1.0278 0.6982 0.4004 0.080 Uiso 1 1 calc R . . . .
C11' C 0.6850(4) 0.5977(3) 0.39267(11) 0.0515(7) Uani 1 1 d . . . . .
C12' C 0.5894(5) 0.6735(3) 0.40572(14) 0.0662(10) Uani 1 1 d . . . . .
H12' H 0.6262 0.7283 0.4219 0.079 Uiso 1 1 calc R . . . .
C13' C 0.4385(5) 0.6691(4) 0.39493(16) 0.0781(12) Uani 1 1 d . . . . .
H13' H 0.3741 0.7202 0.4037 0.094 Uiso 1 1 calc R . . . .
C14' C 0.3878(5) 0.5883(5) 0.37134(15) 0.0788(13) Uani 1 1 d . . . . .
C15' C 0.4776(5) 0.5119(4) 0.35787(14) 0.0745(12) Uani 1 1 d . . . . .
H15' H 0.4393 0.4576 0.3417 0.089 Uiso 1 1 calc R . . . .
C16' C 0.6269(4) 0.5168(3) 0.36864(12) 0.0586(8) Uani 1 1 d . . . . .
H16' H 0.6897 0.4650 0.3597 0.070 Uiso 1 1 calc R . . . .
C17' C 1.1054(4) 0.5481(3) 0.49780(13) 0.0595(9) Uani 1 1 d . . . . .
C18' C 1.2707(5) 0.5514(4) 0.49532(15) 0.0771(12) Uani 1 1 d . . . . .
H18D H 1.3050 0.5037 0.4730 0.116 Uiso 1 1 calc GR . . . .
H18E H 1.3117 0.5353 0.5249 0.116 Uiso 1 1 calc GR . . . .
H18F H 1.3021 0.6174 0.4865 0.116 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.354(6) . ?
O1 C8 1.201(5) . ?
O2 N2 1.201(6) . ?
O3 N2 1.195(5) . ?
O4 C7 1.442(4) . ?
O4 C17 1.343(4) . ?
O5 C17 1.203(5) . ?
N1 H1 0.88(5) . ?
N1 C5 1.399(5) . ?
N1 C8 1.366(5) . ?
N2 C10 1.493(5) . ?
C1 H1A 0.9300 . ?
C1 C2 1.401(6) . ?
C1 C6 1.374(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(6) . ?
C5 C6 1.394(5) . ?
C6 C7 1.497(5) . ?
C7 C8 1.552(5) . ?
C7 C9 1.558(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.527(5) . ?
C9 C11 1.523(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.377(6) . ?
C11 C16 1.383(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.402(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.319(10) . ?
C14 C15 1.354(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.401(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.494(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F1' C14' 1.362(5) . ?
O1' C8' 1.208(5) . ?
O2' N2' 1.203(6) . ?
O3' N2' 1.201(6) . ?
O4' C7' 1.449(4) . ?
O4' C17' 1.340(4) . ?
O5' C17' 1.199(5) . ?
N1' H1' 0.92(5) . ?
N1' C5' 1.406(5) . ?
N1' C8' 1.354(5) . ?
N2' C10' 1.507(5) . ?
C1' H1'A 0.9300 . ?
C1' C2' 1.398(7) . ?
C1' C6' 1.368(6) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.380(8) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.373(7) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.372(6) . ?
C5' C6' 1.391(5) . ?
C6' C7' 1.495(5) . ?
C7' C8' 1.560(5) . ?
C7' C9' 1.553(4) . ?
C9' H9' 0.9800 . ?
C9' C10' 1.522(5) . ?
C9' C11' 1.522(5) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' C12' 1.381(6) . ?
C11' C16' 1.388(5) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.392(6) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.357(8) . ?
C14' C15' 1.358(7) . ?
C15' H15' 0.9300 . ?
C15' C16' 1.378(6) . ?
C16' H16' 0.9300 . ?
C17' C18' 1.487(5) . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O4 C7 117.5(3) . . ?
C5 N1 H1 124(3) . . ?
C8 N1 H1 122(3) . . ?
C8 N1 C5 112.3(3) . . ?
O2 N2 C10 118.9(5) . . ?
O3 N2 O2 122.3(4) . . ?
O3 N2 C10 118.8(4) . . ?
C2 C1 H1A 121.1 . . ?
C6 C1 H1A 121.1 . . ?
C6 C1 C2 117.7(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(4) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 N1 129.2(4) . . ?
C4 C5 C6 121.5(4) . . ?
C6 C5 N1 109.1(3) . . ?
C1 C6 C5 120.7(3) . . ?
C1 C6 C7 130.5(3) . . ?
C5 C6 C7 108.8(3) . . ?
O4 C7 C6 112.3(3) . . ?
O4 C7 C8 114.0(3) . . ?
O4 C7 C9 103.7(2) . . ?
C6 C7 C8 102.5(3) . . ?
C6 C7 C9 113.6(3) . . ?
C8 C7 C9 111.2(3) . . ?
O1 C8 N1 127.1(3) . . ?
O1 C8 C7 126.6(3) . . ?
N1 C8 C7 106.3(3) . . ?
C7 C9 H9 107.0 . . ?
C10 C9 C7 109.9(3) . . ?
C10 C9 H9 107.0 . . ?
C11 C9 C7 111.6(3) . . ?
C11 C9 H9 107.0 . . ?
C11 C9 C10 113.8(3) . . ?
N2 C10 C9 110.2(3) . . ?
N2 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C9 122.4(4) . . ?
C12 C11 C16 118.3(4) . . ?
C16 C11 C9 119.3(4) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(6) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 F1 119.0(7) . . ?
C13 C14 C15 122.9(5) . . ?
C15 C14 F1 118.1(7) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.4(5) . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 120.5(5) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O4 C17 C18 111.3(3) . . ?
O5 C17 O4 123.1(3) . . ?
O5 C17 C18 125.6(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17' O4' C7' 117.9(3) . . ?
C5' N1' H1' 127(3) . . ?
C8' N1' H1' 121(3) . . ?
C8' N1' C5' 111.8(3) . . ?
O2' N2' C10' 117.2(5) . . ?
O3' N2' O2' 124.5(5) . . ?
O3' N2' C10' 118.2(4) . . ?
C2' C1' H1'A 121.0 . . ?
C6' C1' H1'A 121.0 . . ?
C6' C1' C2' 118.1(4) . . ?
C1' C2' H2' 119.8 . . ?
C3' C2' C1' 120.5(4) . . ?
C3' C2' H2' 119.8 . . ?
C2' C3' H3' 119.1 . . ?
C4' C3' C2' 121.7(4) . . ?
C4' C3' H3' 119.1 . . ?
C3' C4' H4' 121.4 . . ?
C5' C4' C3' 117.2(4) . . ?
C5' C4' H4' 121.4 . . ?
C4' C5' N1' 128.0(4) . . ?
C4' C5' C6' 122.3(4) . . ?
C6' C5' N1' 109.8(3) . . ?
C1' C6' C5' 120.2(4) . . ?
C1' C6' C7' 131.3(3) . . ?
C5' C6' C7' 108.5(3) . . ?
O4' C7' C6' 113.4(3) . . ?
O4' C7' C8' 112.9(3) . . ?
O4' C7' C9' 104.3(3) . . ?
C6' C7' C8' 102.4(3) . . ?
C6' C7' C9' 111.8(3) . . ?
C9' C7' C8' 112.3(3) . . ?
O1' C8' N1' 127.3(4) . . ?
O1' C8' C7' 125.9(4) . . ?
N1' C8' C7' 106.8(3) . . ?
C7' C9' H9' 106.9 . . ?
C10' C9' C7' 111.4(3) . . ?
C10' C9' H9' 106.9 . . ?
C10' C9' C11' 112.9(3) . . ?
C11' C9' C7' 111.4(3) . . ?
C11' C9' H9' 106.9 . . ?
N2' C10' C9' 108.3(3) . . ?
N2' C10' H10C 110.0 . . ?
N2' C10' H10D 110.0 . . ?
C9' C10' H10C 110.0 . . ?
C9' C10' H10D 110.0 . . ?
H10C C10' H10D 108.4 . . ?
C12' C11' C9' 123.2(3) . . ?
C12' C11' C16' 118.3(4) . . ?
C16' C11' C9' 118.5(3) . . ?
C11' C12' H12' 119.6 . . ?
C11' C12' C13' 120.9(4) . . ?
C13' C12' H12' 119.6 . . ?
C12' C13' H13' 120.8 . . ?
C14' C13' C12' 118.3(4) . . ?
C14' C13' H13' 120.8 . . ?
C13' C14' F1' 119.0(5) . . ?
C13' C14' C15' 122.9(4) . . ?
C15' C14' F1' 118.1(5) . . ?
C14' C15' H15' 120.8 . . ?
C14' C15' C16' 118.5(4) . . ?
C16' C15' H15' 120.8 . . ?
C11' C16' H16' 119.4 . . ?
C15' C16' C11' 121.2(4) . . ?
C15' C16' H16' 119.4 . . ?
O4' C17' C18' 110.9(3) . . ?
O5' C17' O4' 123.2(3) . . ?
O5' C17' C18' 125.9(4) . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18E 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?

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
N1 H1 O5' 0.88(5) 2.21(5) 3.014(4) 153(4) .
N1' H1' O5 0.92(5) 2.41(5) 3.152(4) 138(4) .

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 C14 C15 C16 178.9(4) . . . . ?
O2 N2 C10 C9 119.5(5) . . . . ?
O3 N2 C10 C9 -62.4(5) . . . . ?
O4 C7 C8 O1 50.8(5) . . . . ?
O4 C7 C8 N1 -131.5(3) . . . . ?
O4 C7 C9 C10 -57.9(4) . . . . ?
O4 C7 C9 C11 174.9(3) . . . . ?
N1 C5 C6 C1 176.7(3) . . . . ?
N1 C5 C6 C7 -1.9(4) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C1 C6 C7 O4 -48.5(5) . . . . ?
C1 C6 C7 C8 -171.2(4) . . . . ?
C1 C6 C7 C9 68.8(5) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
C2 C1 C6 C7 178.0(4) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 N1 -175.9(4) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C5 N1 C8 O1 -172.7(4) . . . . ?
C5 N1 C8 C7 9.7(4) . . . . ?
C5 C6 C7 O4 129.8(3) . . . . ?
C5 C6 C7 C8 7.1(3) . . . . ?
C5 C6 C7 C9 -112.9(3) . . . . ?
C6 C1 C2 C3 0.8(7) . . . . ?
C6 C7 C8 O1 172.4(4) . . . . ?
C6 C7 C8 N1 -10.0(3) . . . . ?
C6 C7 C9 C10 180.0(3) . . . . ?
C6 C7 C9 C11 52.7(4) . . . . ?
C7 O4 C17 O5 -9.1(6) . . . . ?
C7 O4 C17 C18 168.6(4) . . . . ?
C7 C9 C10 N2 174.3(3) . . . . ?
C7 C9 C11 C12 87.2(4) . . . . ?
C7 C9 C11 C16 -91.6(4) . . . . ?
C8 N1 C5 C4 171.7(4) . . . . ?
C8 N1 C5 C6 -5.2(4) . . . . ?
C8 C7 C9 C10 65.0(4) . . . . ?
C8 C7 C9 C11 -62.2(4) . . . . ?
C9 C7 C8 O1 -66.0(5) . . . . ?
C9 C7 C8 N1 111.7(3) . . . . ?
C9 C11 C12 C13 -179.4(4) . . . . ?
C9 C11 C16 C15 177.8(4) . . . . ?
C10 C9 C11 C12 -38.0(5) . . . . ?
C10 C9 C11 C16 143.3(3) . . . . ?
C11 C9 C10 N2 -59.6(4) . . . . ?
C11 C12 C13 C14 1.1(8) . . . . ?
C12 C11 C16 C15 -1.0(6) . . . . ?
C12 C13 C14 F1 179.4(5) . . . . ?
C12 C13 C14 C15 0.2(9) . . . . ?
C13 C14 C15 C16 -1.9(8) . . . . ?
C14 C15 C16 C11 2.3(7) . . . . ?
C16 C11 C12 C13 -0.7(6) . . . . ?
C17 O4 C7 C6 -64.7(4) . . . . ?
C17 O4 C7 C8 51.3(4) . . . . ?
C17 O4 C7 C9 172.3(3) . . . . ?
F1' C14' C15' C16' -179.6(4) . . . . ?
O2' N2' C10' C9' 121.8(4) . . . . ?
O3' N2' C10' C9' -59.2(6) . . . . ?
O4' C7' C8' O1' 51.4(5) . . . . ?
O4' C7' C8' N1' -131.0(3) . . . . ?
O4' C7' C9' C10' -49.9(4) . . . . ?
O4' C7' C9' C11' -176.9(3) . . . . ?
N1' C5' C6' C1' 178.6(3) . . . . ?
N1' C5' C6' C7' -2.1(4) . . . . ?
C1' C2' C3' C4' 0.1(7) . . . . ?
C1' C6' C7' O4' -52.4(5) . . . . ?
C1' C6' C7' C8' -174.4(4) . . . . ?
C1' C6' C7' C9' 65.2(5) . . . . ?
C2' C1' C6' C5' 0.0(6) . . . . ?
C2' C1' C6' C7' -179.1(4) . . . . ?
C2' C3' C4' C5' -0.9(7) . . . . ?
C3' C4' C5' N1' -178.0(4) . . . . ?
C3' C4' C5' C6' 1.4(6) . . . . ?
C4' C5' C6' C1' -0.9(5) . . . . ?
C4' C5' C6' C7' 178.4(3) . . . . ?
C5' N1' C8' O1' -174.4(4) . . . . ?
C5' N1' C8' C7' 8.0(4) . . . . ?
C5' C6' C7' O4' 128.4(3) . . . . ?
C5' C6' C7' C8' 6.4(3) . . . . ?
C5' C6' C7' C9' -114.0(3) . . . . ?
C6' C1' C2' C3' 0.4(7) . . . . ?
C6' C7' C8' O1' 173.7(4) . . . . ?
C6' C7' C8' N1' -8.7(3) . . . . ?
C6' C7' C9' C10' -172.8(3) . . . . ?
C6' C7' C9' C11' 60.2(4) . . . . ?
C7' O4' C17' O5' -5.8(6) . . . . ?
C7' O4' C17' C18' 172.7(4) . . . . ?
C7' C9' C10' N2' 177.8(3) . . . . ?
C7' C9' C11' C12' 84.8(4) . . . . ?
C7' C9' C11' C16' -96.0(4) . . . . ?
C8' N1' C5' C4' 175.4(4) . . . . ?
C8' N1' C5' C6' -4.0(4) . . . . ?
C8' C7' C9' C10' 72.7(4) . . . . ?
C8' C7' C9' C11' -54.3(4) . . . . ?
C9' C7' C8' O1' -66.3(5) . . . . ?
C9' C7' C8' N1' 111.4(3) . . . . ?
C9' C11' C12' C13' 179.1(4) . . . . ?
C9' C11' C16' C15' -179.1(3) . . . . ?
C10' C9' C11' C12' -41.4(5) . . . . ?
C10' C9' C11' C16' 137.8(3) . . . . ?
C11' C9' C10' N2' -56.0(5) . . . . ?
C11' C12' C13' C14' 0.1(7) . . . . ?
C12' C11' C16' C15' 0.1(5) . . . . ?
C12' C13' C14' F1' 179.6(4) . . . . ?
C12' C13' C14' C15' 0.0(7) . . . . ?
C13' C14' C15' C16' 0.0(7) . . . . ?
C14' C15' C16' C11' 0.0(6) . . . . ?
C16' C11' C12' C13' -0.2(6) . . . . ?
C17' O4' C7' C6' -63.6(4) . . . . ?
C17' O4' C7' C8' 52.3(4) . . . . ?
C17' O4' C7' C9' 174.5(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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.913
