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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_b
_database_code_depnum_ccdc_archive 'CCDC 1910839'
_audit_update_record             
;
2019-08-07 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2019-02-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.6213(13)
_cell_length_b                   15.810(3)
_cell_length_c                   16.409(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1717.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         3.318
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2516
_reflns_number_total             3936
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0784
_refine_ls_restrained_S_all      1.047
_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)+(0.0625P)²+0.5504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1596
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B), C16(H16A,H16B), C15(H15A,H15B), C14(H14A,H14B)
2.c Me refined with riding coordinates:
 C18(H18A,H18B,H18C), C13(H13A,H13B,H13C)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4)
2.e Tetrahedral OH refined with riding coordinates:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C10 C 0.0595(9) 0.1212(3) 0.3967(4) 0.0595(14) Uani 1 1 d . . . . .
C2 C 0.0607(7) 0.2106(2) 0.4261(3) 0.0451(11) Uani 1 1 d . . . . .
C1 C 0.0614(8) 0.2723(3) 0.3686(3) 0.0471(11) Uani 1 1 d . . . . .
H1 H 0.0583 0.2560 0.3142 0.057 Uiso 1 1 calc R . . . .
C11 C 0.0513(10) 0.4195(3) 0.3202(3) 0.0544(14) Uani 1 1 d . . . . .
H11 H 0.1144 0.3971 0.2706 0.065 Uiso 1 1 calc R . . . .
C12 C 0.1667(8) 0.4961(3) 0.3478(3) 0.0527(13) Uani 1 1 d . . . . .
H12A H 0.3079 0.4814 0.3549 0.063 Uiso 1 1 calc R . . . .
H12B H 0.1583 0.5397 0.3064 0.063 Uiso 1 1 calc R . . . .
C7 C 0.0807(7) 0.4689(2) 0.4840(2) 0.0356(10) Uani 1 1 d . . . . .
C8 C 0.0703(7) 0.3818(2) 0.4660(2) 0.0358(10) Uani 1 1 d . . . . .
C9 C 0.0628(7) 0.3222(2) 0.5294(3) 0.0363(10) Uani 1 1 d . . . . .
C3 C 0.0599(7) 0.2320(3) 0.5108(3) 0.0429(11) Uani 1 1 d . . . . .
C4 C 0.0577(7) 0.3510(3) 0.6098(2) 0.0397(10) Uani 1 1 d . . . . .
H4 H 0.0502 0.3127 0.6527 0.048 Uiso 1 1 calc R . . . .
C5 C 0.0638(7) 0.4346(3) 0.6247(2) 0.0388(10) Uani 1 1 d . . . . .
C6 C 0.0816(7) 0.4969(2) 0.5640(3) 0.0357(10) Uani 1 1 d . . . . .
C17 C -0.0829(9) 0.6300(3) 0.5958(4) 0.0653(15) Uani 1 1 d . . . . .
H17A H -0.1805 0.5969 0.6261 0.078 Uiso 1 1 calc R . . . .
H17B H -0.1393 0.6419 0.5424 0.078 Uiso 1 1 calc R . . . .
C16 C -0.0419(10) 0.7121(3) 0.6400(4) 0.0686(16) Uani 1 1 d . . . . .
H16A H -0.1651 0.7452 0.6424 0.082 Uiso 1 1 calc R . . . .
H16B H -0.0002 0.6999 0.6954 0.082 Uiso 1 1 calc R . . . .
C18 C 0.1496(11) 0.8419(3) 0.6408(4) 0.086(2) Uani 1 1 d . . . . .
H18A H 0.0258 0.8733 0.6433 0.129 Uiso 1 1 calc R . . . .
H18B H 0.1983 0.8317 0.6950 0.129 Uiso 1 1 calc R . . . .
H18C H 0.2484 0.8736 0.6109 0.129 Uiso 1 1 calc R . . . .
C15 C 0.2979(8) 0.7124(3) 0.5954(3) 0.0574(14) Uani 1 1 d . . . . .
H15A H 0.3449 0.6999 0.6500 0.069 Uiso 1 1 calc R . . . .
H15B H 0.4010 0.7456 0.5681 0.069 Uiso 1 1 calc R . . . .
C14 C 0.2644(9) 0.6305(3) 0.5492(4) 0.0667(17) Uani 1 1 d . . . . .
H14A H 0.2299 0.6429 0.4930 0.080 Uiso 1 1 calc R . . . .
H14B H 0.3876 0.5973 0.5495 0.080 Uiso 1 1 calc R . . . .
F1 F 0.0600(5) 0.46220(16) 0.70285(14) 0.0577(8) Uani 1 1 d . . . . .
N1 N 0.0664(7) 0.3553(2) 0.38521(19) 0.0407(9) Uani 1 1 d . . . . .
N2 N 0.1024(6) 0.5828(2) 0.5870(2) 0.0418(10) Uani 1 1 d . . . . .
N3 N 0.1134(8) 0.7606(3) 0.5997(3) 0.0633(13) Uani 1 1 d . . . . .
O1 O 0.0673(6) 0.0637(2) 0.4566(3) 0.0740(12) Uani 1 1 d . . . . .
H1A H 0.0723 0.0879 0.5008 0.111 Uiso 1 1 calc R . . . .
O2 O 0.0511(7) 0.1007(2) 0.3269(3) 0.0801(13) Uani 1 1 d . . . . .
O3 O 0.0579(6) 0.17755(18) 0.5670(2) 0.0569(9) Uani 1 1 d . . . . .
O4 O 0.0874(6) 0.52781(17) 0.42313(16) 0.0467(8) Uani 1 1 d . . . . .
C13 C -0.1712(10) 0.4382(4) 0.3026(4) 0.0735(19) Uani 1 1 d . . . . .
H13A H -0.1807 0.4800 0.2603 0.110 Uiso 1 1 calc R . . . .
H13B H -0.2375 0.3873 0.2853 0.110 Uiso 1 1 calc R . . . .
H13C H -0.2349 0.4592 0.3511 0.110 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C10 C2 1.494(6) . ?
C10 O1 1.340(7) . ?
C10 O2 1.192(7) . ?
C2 C1 1.357(7) . ?
C2 C3 1.431(7) . ?
C1 H1 0.9300 . ?
C1 N1 1.340(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.502(6) . ?
C11 N1 1.475(6) . ?
C11 C13 1.530(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 O4 1.434(5) . ?
C7 C8 1.410(5) . ?
C7 C6 1.386(5) . ?
C7 O4 1.366(5) . ?
C8 C9 1.404(6) . ?
C8 N1 1.391(5) . ?
C9 C3 1.459(6) . ?
C9 C4 1.396(6) . ?
C3 O3 1.263(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.344(6) . ?
C5 C6 1.405(6) . ?
C5 F1 1.355(4) . ?
C6 N2 1.416(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.511(7) . ?
C17 N2 1.444(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 N3 1.443(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 N3 1.471(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.516(7) . ?
C15 N3 1.441(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 N2 1.451(6) . ?
O1 H1A 0.8200 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C10 C2 113.9(5) . . ?
O2 C10 C2 124.6(6) . . ?
O2 C10 O1 121.5(5) . . ?
C1 C2 C10 117.2(5) . . ?
C1 C2 C3 120.3(4) . . ?
C3 C2 C10 122.5(4) . . ?
C2 C1 H1 117.9 . . ?
N1 C1 C2 124.3(4) . . ?
N1 C1 H1 117.9 . . ?
C12 C11 H11 108.9 . . ?
C12 C11 C13 113.0(5) . . ?
N1 C11 H11 108.9 . . ?
N1 C11 C12 107.6(4) . . ?
N1 C11 C13 109.6(4) . . ?
C13 C11 H11 108.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O4 C12 C11 110.8(4) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
C6 C7 C8 120.7(4) . . ?
O4 C7 C8 121.0(3) . . ?
O4 C7 C6 118.3(3) . . ?
C9 C8 C7 120.1(4) . . ?
N1 C8 C7 119.6(3) . . ?
N1 C8 C9 120.3(3) . . ?
C8 C9 C3 120.1(4) . . ?
C4 C9 C8 118.8(4) . . ?
C4 C9 C3 121.1(4) . . ?
C2 C3 C9 115.8(4) . . ?
O3 C3 C2 123.3(4) . . ?
O3 C3 C9 120.9(4) . . ?
C9 C4 H4 120.3 . . ?
C5 C4 C9 119.5(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 124.2(4) . . ?
C4 C5 F1 119.2(4) . . ?
F1 C5 C6 116.5(3) . . ?
C7 C6 C5 116.5(3) . . ?
C7 C6 N2 124.0(4) . . ?
C5 C6 N2 119.4(4) . . ?
H17A C17 H17B 108.2 . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
N2 C17 H17A 109.7 . . ?
N2 C17 H17B 109.7 . . ?
N2 C17 C16 109.8(5) . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N3 C16 C17 111.4(5) . . ?
N3 C16 H16A 109.4 . . ?
N3 C16 H16B 109.4 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 C14 110.6(5) . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
N2 C14 C15 109.8(4) . . ?
N2 C14 H14A 109.7 . . ?
N2 C14 H14B 109.7 . . ?
C1 N1 C11 121.6(4) . . ?
C1 N1 C8 119.2(4) . . ?
C8 N1 C11 118.9(3) . . ?
C6 N2 C17 116.1(4) . . ?
C6 N2 C14 117.2(4) . . ?
C17 N2 C14 113.7(4) . . ?
C16 N3 C18 111.8(4) . . ?
C15 N3 C16 110.3(4) . . ?
C15 N3 C18 110.3(5) . . ?
C10 O1 H1A 109.5 . . ?
C7 O4 C12 113.8(3) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C10 C2 C1 N1 -178.7(5) . . . . ?
C10 C2 C3 C9 179.6(4) . . . . ?
C10 C2 C3 O3 -0.1(8) . . . . ?
C2 C1 N1 C11 -175.3(5) . . . . ?
C2 C1 N1 C8 -0.3(8) . . . . ?
C1 C2 C3 C9 -0.8(7) . . . . ?
C1 C2 C3 O3 179.5(5) . . . . ?
C11 C12 O4 C7 55.1(5) . . . . ?
C12 C11 N1 C1 -150.2(5) . . . . ?
C12 C11 N1 C8 34.8(7) . . . . ?
C7 C8 C9 C3 -177.6(4) . . . . ?
C7 C8 C9 C4 2.5(8) . . . . ?
C7 C8 N1 C1 178.4(4) . . . . ?
C7 C8 N1 C11 -6.5(7) . . . . ?
C7 C6 N2 C17 90.7(6) . . . . ?
C7 C6 N2 C14 -48.3(7) . . . . ?
C8 C7 C6 C5 -2.4(7) . . . . ?
C8 C7 C6 N2 176.6(4) . . . . ?
C8 C7 O4 C12 -24.9(6) . . . . ?
C8 C9 C3 C2 -1.3(7) . . . . ?
C8 C9 C3 O3 178.4(5) . . . . ?
C8 C9 C4 C5 -1.2(8) . . . . ?
C9 C8 N1 C1 -2.0(8) . . . . ?
C9 C8 N1 C11 173.2(5) . . . . ?
C9 C4 C5 C6 -2.1(8) . . . . ?
C9 C4 C5 F1 -179.6(4) . . . . ?
C3 C2 C1 N1 1.7(8) . . . . ?
C3 C9 C4 C5 178.9(4) . . . . ?
C4 C9 C3 C2 178.5(4) . . . . ?
C4 C9 C3 O3 -1.8(8) . . . . ?
C4 C5 C6 C7 3.9(8) . . . . ?
C4 C5 C6 N2 -175.1(5) . . . . ?
C5 C6 N2 C17 -90.4(6) . . . . ?
C5 C6 N2 C14 130.7(5) . . . . ?
C6 C7 C8 C9 -0.6(8) . . . . ?
C6 C7 C8 N1 179.0(4) . . . . ?
C6 C7 O4 C12 156.0(4) . . . . ?
C17 C16 N3 C18 178.1(5) . . . . ?
C17 C16 N3 C15 -58.9(6) . . . . ?
C16 C17 N2 C6 166.0(4) . . . . ?
C16 C17 N2 C14 -53.7(6) . . . . ?
C15 C14 N2 C6 -165.8(4) . . . . ?
C15 C14 N2 C17 54.2(6) . . . . ?
C14 C15 N3 C16 59.1(6) . . . . ?
C14 C15 N3 C18 -177.1(5) . . . . ?
F1 C5 C6 C7 -178.5(4) . . . . ?
F1 C5 C6 N2 2.5(7) . . . . ?
N1 C11 C12 O4 -58.5(6) . . . . ?
N1 C8 C9 C3 2.7(7) . . . . ?
N1 C8 C9 C4 -177.1(4) . . . . ?
N2 C17 C16 N3 55.2(7) . . . . ?
N3 C15 C14 N2 -56.0(6) . . . . ?
O1 C10 C2 C1 177.4(5) . . . . ?
O1 C10 C2 C3 -3.0(8) . . . . ?
O2 C10 C2 C1 -3.1(9) . . . . ?
O2 C10 C2 C3 176.5(5) . . . . ?
O4 C7 C8 C9 -179.8(4) . . . . ?
O4 C7 C8 N1 -0.1(7) . . . . ?
O4 C7 C6 C5 176.7(4) . . . . ?
O4 C7 C6 N2 -4.3(7) . . . . ?
C13 C11 C12 O4 62.6(5) . . . . ?
C13 C11 N1 C1 86.6(6) . . . . ?
C13 C11 N1 C8 -88.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_r20190117d1
_database_code_depnum_ccdc_archive 'CCDC 1910840'
_audit_update_record             
;
2019-08-07 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2019-03-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.5(C2 H6 O2), 0.5(C2 O2)'
_chemical_formula_sum            'C20 H26 F N3 O6'
_chemical_formula_weight         423.44
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.353(4)
_cell_length_b                   6.784(3)
_cell_length_c                   18.680(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.31(3)
_cell_angle_gamma                90
_cell_volume                     2121.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7112
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8984
_cell_measurement_theta_min      1.4252
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9926
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.261
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3071
_reflns_number_total             3673
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_extinction_coef       0.035(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3673
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0888
_refine_ls_restrained_S_all      1.061
_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)+(0.1967P)²+0.1428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2529
_refine_ls_wR_factor_ref         0.2662
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -3(2)
 4(2)
2. 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, All O(H) groups
3. Restrained distances
 O1S-C1S = O2S-C2S
 1.4 with sigma of 0.01
 C1S-C2S
 1.54 with sigma of 0.01
 O4S-C4S = O3S-C3S
 1.4 with sigma of 0.01
 C4S-C3S
 1.54 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
O4S \\sim O3S \\sim C4S \\sim C3S: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C18) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O4S) \\sim Ueq, Uanis(O3S) \\sim Ueq, Uanis(C4S) \\sim Ueq, Uanis(C3S)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: O1S(0.5) H1S(0.5) O2S(0.5) H2S(0.5) C1S(0.5) H1SA(0.5) H1SB(0.5)
 C2S(0.5) H2SA(0.5) H2SB(0.5) O4S(0.5) O3S(0.5) C4S(0.5) C3S(0.5)
6.a Ternary CH refined with riding coordinates:
 C11(H11)
6.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C14(H14A,H14B), C15(H15A,H15B), C12(H12A,
 H12B), C1S(H1SA,H1SB), C2S(H2SA,H2SB)
6.c Me refined with riding coordinates:
 C18(H18A,H18B,H18C), C13(H13A,H13B,H13C)
6.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1A)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1S(H1S), O2S(H2S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.95727(17) 0.9444(7) 0.90409(17) 0.0482(10) Uani 1 1 d . . . A 5
O4 O 0.6850(2) 0.8995(7) 0.7713(2) 0.0448(11) Uani 1 1 d . . . A 5
O3 O 0.8111(2) 0.9331(7) 1.10376(19) 0.0417(10) Uani 1 1 d . . . A 5
O1 O 0.7010(3) 0.9242(8) 1.1681(2) 0.0514(11) Uani 1 1 d . . . A 5
H1 H 0.7462 0.9150 1.1599 0.077 Uiso 1 1 calc GR . . A 5
O2 O 0.5748(2) 0.9242(8) 1.1024(2) 0.0536(12) Uani 1 1 d . . . A 5
N3 N 0.8444(4) 1.0281(11) 0.6220(3) 0.0642(18) Uani 1 1 d . . . A 5
N2 N 0.8435(3) 0.9261(10) 0.7694(3) 0.0478(13) Uani 1 1 d . . . A 5
N1 N 0.6410(3) 0.9114(7) 0.9053(3) 0.0370(11) Uani 1 1 d . . . A 5
C18 C 0.8118(7) 1.131(2) 0.5524(5) 0.094(3) Uani 1 1 d . U . A 5
H18A H 0.7966 1.0351 0.5119 0.142 Uiso 1 1 calc R . . A 5
H18B H 0.7646 1.2064 0.5555 0.142 Uiso 1 1 calc R . . A 5
H18C H 0.8521 1.2212 0.5429 0.142 Uiso 1 1 calc R . . A 5
C16 C 0.8675(5) 1.1682(12) 0.6833(4) 0.0598(19) Uani 1 1 d . . . A 5
H16A H 0.8201 1.2459 0.6861 0.072 Uiso 1 1 calc R . . A 5
H16B H 0.9076 1.2607 0.6735 0.072 Uiso 1 1 calc R . . A 5
C17 C 0.9015(4) 1.0669(12) 0.7562(4) 0.0510(16) Uani 1 1 d . . . A 5
H17A H 0.9515 0.9975 0.7552 0.061 Uiso 1 1 calc R . . A 5
H17B H 0.9143 1.1654 0.7967 0.061 Uiso 1 1 calc R . . A 5
C14 C 0.8160(4) 0.7843(11) 0.7106(3) 0.0480(16) Uani 1 1 d . . . A 5
H14A H 0.7734 0.7019 0.7217 0.058 Uiso 1 1 calc R . . A 5
H14B H 0.8607 0.6967 0.7078 0.058 Uiso 1 1 calc R . . A 5
C15 C 0.7837(4) 0.8876(14) 0.6367(4) 0.061(2) Uani 1 1 d . . . A 5
H15A H 0.7699 0.7885 0.5964 0.074 Uiso 1 1 calc R . . A 5
H15B H 0.7345 0.9606 0.6372 0.074 Uiso 1 1 calc R . . A 5
C6 C 0.8221(3) 0.9236(10) 0.8357(3) 0.0372(12) Uani 1 1 d . . . A 5
C5 C 0.8786(3) 0.9360(9) 0.9039(3) 0.0364(12) Uani 1 1 d . . . A 5
C4 C 0.8611(3) 0.9375(9) 0.9715(3) 0.0360(12) Uani 1 1 d . . . A 5
H4 H 0.9024 0.9463 1.0164 0.043 Uiso 1 1 calc R . . A 5
C9 C 0.7814(3) 0.9258(9) 0.9725(3) 0.0331(11) Uani 1 1 d . . . A 5
C3 C 0.7593(3) 0.9274(8) 1.0426(3) 0.0371(12) Uani 1 1 d . . . A 5
C2 C 0.6752(3) 0.9241(9) 1.0369(3) 0.0362(12) Uani 1 1 d . . . A 5
C1 C 0.6196(3) 0.9196(9) 0.9690(3) 0.0400(13) Uani 1 1 d . . . A 5
H1A H 0.5644 0.9223 0.9673 0.048 Uiso 1 1 calc R . . A 5
C8 C 0.7216(3) 0.9149(8) 0.9048(3) 0.0337(12) Uani 1 1 d . . . A 5
C7 C 0.7419(3) 0.9112(9) 0.8374(3) 0.0369(12) Uani 1 1 d . . . A 5
C12 C 0.6120(3) 0.8020(10) 0.7775(3) 0.0423(14) Uani 1 1 d . . . A 5
H12A H 0.6238 0.6639 0.7939 0.051 Uiso 1 1 calc R . . A 5
H12B H 0.5722 0.8004 0.7285 0.051 Uiso 1 1 calc R . . A 5
C11 C 0.5785(3) 0.9112(10) 0.8329(3) 0.0423(14) Uani 1 1 d . . . A 5
H11 H 0.5312 0.8363 0.8395 0.051 Uiso 1 1 calc R . . A 5
C13 C 0.5521(4) 1.1163(11) 0.8094(4) 0.0537(17) Uani 1 1 d . . . A 5
H13A H 0.5112 1.1123 0.7619 0.080 Uiso 1 1 calc R . . A 5
H13B H 0.5299 1.1777 0.8471 0.080 Uiso 1 1 calc R . . A 5
H13C H 0.5980 1.1933 0.8039 0.080 Uiso 1 1 calc R . . A 5
C10 C 0.6453(3) 0.9260(10) 1.1045(3) 0.0427(13) Uani 1 1 d . . . A 5
O1S O 0.4712(5) 0.3129(17) 0.5973(6) 0.060(3) Uani 0.5 1 d D . P B 1
H1S H 0.4731 0.1906 0.6044 0.089 Uiso 0.5 1 calc GR . P B 1
O2S O 0.5239(6) 0.7416(14) 0.5978(5) 0.059(3) Uani 0.5 1 d D . P B 1
H2S H 0.4835 0.6984 0.6095 0.088 Uiso 0.5 1 calc GR . P B 1
C1S C 0.5468(6) 0.3963(18) 0.6311(6) 0.059(4) Uani 0.5 1 d D . P B 1
H1SA H 0.5872 0.2914 0.6342 0.070 Uiso 0.5 1 calc R . P B 1
H1SB H 0.5473 0.4309 0.6827 0.070 Uiso 0.5 1 calc R . P B 1
C2S C 0.5766(8) 0.5838(17) 0.5957(7) 0.053(3) Uani 0.5 1 d D . P B 1
H2SA H 0.6316 0.6187 0.6240 0.064 Uiso 0.5 1 calc R . P B 1
H2SB H 0.5769 0.5559 0.5437 0.064 Uiso 0.5 1 calc R . P B 1
O4S O 0.4103(7) 1.0865(17) 0.4497(6) 0.067(3) Uani 0.5 1 d D U P C 2
O3S O 0.4903(7) 0.9329(18) 0.5952(5) 0.065(2) Uani 0.5 1 d D U P C 2
C4S C 0.4582(16) 0.920(4) 0.4542(13) 0.104(5) Uani 0.5 1 d D U P C 2
C3S C 0.5182(13) 0.924(5) 0.5317(10) 0.099(5) Uani 0.5 1 d D U P C 2


_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 C5 1.366(6) . ?
O4 C7 1.365(7) . ?
O4 C12 1.460(7) . ?
O3 C3 1.254(7) . ?
O1 H1 0.8400 . ?
O1 C10 1.319(7) . ?
O2 C10 1.214(7) . ?
N3 C18 1.453(11) . ?
N3 C16 1.459(10) . ?
N3 C15 1.498(10) . ?
N2 C17 1.455(8) . ?
N2 C14 1.443(8) . ?
N2 C6 1.385(7) . ?
N1 C1 1.337(7) . ?
N1 C8 1.402(6) . ?
N1 C11 1.493(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.500(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.518(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C6 C5 1.390(7) . ?
C6 C7 1.403(7) . ?
C5 C4 1.373(8) . ?
C4 H4 0.9500 . ?
C4 C9 1.390(7) . ?
C9 C3 1.459(7) . ?
C9 C8 1.411(7) . ?
C3 C2 1.436(7) . ?
C2 C1 1.376(8) . ?
C2 C10 1.486(7) . ?
C1 H1A 0.9500 . ?
C8 C7 1.394(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.509(9) . ?
C11 H11 1.0000 . ?
C11 C13 1.494(10) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O1S H1S 0.8400 . ?
O1S C1S 1.415(11) . ?
O2S H2S 0.8400 . ?
O2S C2S 1.415(11) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.583(11) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
O4S C4S 1.394(14) . ?
O4S C3S 1.63(3) 2_656 ?
O3S C4S 1.45(3) 2_656 ?
O3S C3S 1.395(14) . ?
C4S O3S 1.45(3) 2_656 ?
C4S C4S 1.93(4) 2_656 ?
C4S C3S 1.543(13) . ?
C4S C3S 0.43(4) 2_656 ?
C3S O4S 1.63(3) 2_656 ?
C3S C4S 0.43(4) 2_656 ?
C3S C3S 1.19(4) 2_656 ?

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
C7 O4 C12 113.0(4) . . ?
C10 O1 H1 109.5 . . ?
C18 N3 C16 110.5(8) . . ?
C18 N3 C15 110.0(7) . . ?
C16 N3 C15 109.3(5) . . ?
C14 N2 C17 114.4(5) . . ?
C6 N2 C17 121.4(5) . . ?
C6 N2 C14 124.0(5) . . ?
C1 N1 C8 121.1(5) . . ?
C1 N1 C11 120.0(4) . . ?
C8 N1 C11 118.7(4) . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
N3 C16 C17 111.9(6) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
N2 C17 C16 109.3(6) . . ?
N2 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 C15 110.6(7) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
N3 C15 C14 110.6(5) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N2 C6 C5 121.9(5) . . ?
N2 C6 C7 121.6(5) . . ?
C5 C6 C7 116.5(5) . . ?
F1 C5 C6 117.8(4) . . ?
F1 C5 C4 117.5(4) . . ?
C4 C5 C6 124.7(5) . . ?
C5 C4 H4 120.9 . . ?
C5 C4 C9 118.3(5) . . ?
C9 C4 H4 120.9 . . ?
C4 C9 C3 120.6(5) . . ?
C4 C9 C8 119.4(5) . . ?
C8 C9 C3 120.0(5) . . ?
O3 C3 C9 121.6(5) . . ?
O3 C3 C2 122.5(5) . . ?
C2 C3 C9 115.9(5) . . ?
C3 C2 C10 120.8(5) . . ?
C1 C2 C3 121.3(5) . . ?
C1 C2 C10 117.8(5) . . ?
N1 C1 C2 122.0(5) . . ?
N1 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
N1 C8 C9 119.6(4) . . ?
C7 C8 N1 119.8(5) . . ?
C7 C8 C9 120.5(5) . . ?
O4 C7 C6 117.9(5) . . ?
O4 C7 C8 121.5(5) . . ?
C8 C7 C6 120.6(5) . . ?
O4 C12 H12A 109.8 . . ?
O4 C12 H12B 109.8 . . ?
O4 C12 C11 109.3(5) . . ?
H12A C12 H12B 108.3 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
N1 C11 C12 107.6(4) . . ?
N1 C11 H11 108.2 . . ?
N1 C11 C13 111.0(5) . . ?
C12 C11 H11 108.2 . . ?
C13 C11 C12 113.5(5) . . ?
C13 C11 H11 108.2 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C10 C2 115.4(5) . . ?
O2 C10 O1 121.4(5) . . ?
O2 C10 C2 123.2(5) . . ?
C1S O1S H1S 109.5 . . ?
C2S O2S H2S 109.5 . . ?
O1S C1S H1SA 107.3 . . ?
O1S C1S H1SB 107.3 . . ?
O1S C1S C2S 120.1(10) . . ?
H1SA C1S H1SB 106.9 . . ?
C2S C1S H1SA 107.3 . . ?
C2S C1S H1SB 107.3 . . ?
O2S C2S C1S 108.1(9) . . ?
O2S C2S H2SA 110.1 . . ?
O2S C2S H2SB 110.1 . . ?
C1S C2S H2SA 110.1 . . ?
C1S C2S H2SB 110.1 . . ?
H2SA C2S H2SB 108.4 . . ?
C4S O4S C3S 14(2) . 2_656 ?
C3S O3S C4S 17.1(17) . 2_656 ?
O4S C4S O3S 112(2) . 2_656 ?
O4S C4S C4S 110.5(14) . 2_656 ?
O4S C4S C3S 106(2) . . ?
O3S C4S C4S 97(2) 2_656 2_656 ?
O3S C4S C3S 102.8(16) 2_656 . ?
C3S C4S O4S 116(7) 2_656 . ?
C3S C4S O3S 75(5) 2_656 2_656 ?
C3S C4S C4S 6.1(12) . 2_656 ?
C3S C4S C4S 22(4) 2_656 2_656 ?
C3S C4S C3S 28(5) 2_656 . ?
O3S C3S O4S 101.9(15) . 2_656 ?
O3S C3S C4S 120.0(17) . . ?
C4S C3S O4S 50(5) 2_656 2_656 ?
C4S C3S O4S 120(2) . 2_656 ?
C4S C3S O3S 88(5) 2_656 . ?
C4S C3S C4S 151(5) 2_656 . ?
C4S C3S C3S 142(6) 2_656 2_656 ?
C3S C3S O4S 112.9(14) 2_656 2_656 ?
C3S C3S O3S 130(3) 2_656 . ?
C3S C3S C4S 10(2) 2_656 . ?

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 C5 C4 C9 -179.0(5) . . . . ?
O4 C12 C11 N1 -58.7(6) . . . . ?
O4 C12 C11 C13 64.5(6) . . . . ?
O3 C3 C2 C1 179.4(6) . . . . ?
O3 C3 C2 C10 -0.4(9) . . . . ?
N3 C16 C17 N2 -57.1(7) . . . . ?
N2 C14 C15 N3 53.8(7) . . . . ?
N2 C6 C5 F1 -2.1(10) . . . . ?
N2 C6 C5 C4 178.9(7) . . . . ?
N2 C6 C7 O4 0.7(10) . . . . ?
N2 C6 C7 C8 -178.0(5) . . . . ?
N1 C8 C7 O4 -1.6(9) . . . . ?
N1 C8 C7 C6 177.1(5) . . . . ?
C18 N3 C16 C17 -180.0(6) . . . . ?
C18 N3 C15 C14 -178.0(7) . . . . ?
C16 N3 C15 C14 -56.5(8) . . . . ?
C17 N2 C14 C15 -54.2(7) . . . . ?
C17 N2 C6 C5 -45.0(10) . . . . ?
C17 N2 C6 C7 134.0(7) . . . . ?
C14 N2 C17 C16 55.0(8) . . . . ?
C14 N2 C6 C5 130.2(7) . . . . ?
C14 N2 C6 C7 -50.8(10) . . . . ?
C15 N3 C16 C17 58.8(8) . . . . ?
C6 N2 C17 C16 -129.4(7) . . . . ?
C6 N2 C14 C15 130.3(6) . . . . ?
C6 C5 C4 C9 0.0(10) . . . . ?
C5 C6 C7 O4 179.8(5) . . . . ?
C5 C6 C7 C8 1.1(10) . . . . ?
C5 C4 C9 C3 -179.8(5) . . . . ?
C5 C4 C9 C8 -0.6(9) . . . . ?
C4 C9 C3 O3 -2.2(9) . . . . ?
C4 C9 C3 C2 177.1(5) . . . . ?
C4 C9 C8 N1 -177.4(6) . . . . ?
C4 C9 C8 C7 1.5(9) . . . . ?
C9 C3 C2 C1 0.1(8) . . . . ?
C9 C3 C2 C10 -179.8(5) . . . . ?
C9 C8 C7 O4 179.6(5) . . . . ?
C9 C8 C7 C6 -1.7(9) . . . . ?
C3 C9 C8 N1 1.9(8) . . . . ?
C3 C9 C8 C7 -179.3(5) . . . . ?
C3 C2 C1 N1 2.3(9) . . . . ?
C3 C2 C10 O1 -2.2(9) . . . . ?
C3 C2 C10 O2 179.7(6) . . . . ?
C1 N1 C8 C9 0.5(8) . . . . ?
C1 N1 C8 C7 -178.4(5) . . . . ?
C1 N1 C11 C12 -151.7(5) . . . . ?
C1 N1 C11 C13 83.5(7) . . . . ?
C1 C2 C10 O1 178.0(6) . . . . ?
C1 C2 C10 O2 -0.2(10) . . . . ?
C8 N1 C1 C2 -2.6(9) . . . . ?
C8 N1 C11 C12 32.1(7) . . . . ?
C8 N1 C11 C13 -92.7(6) . . . . ?
C8 C9 C3 O3 178.6(6) . . . . ?
C8 C9 C3 C2 -2.1(8) . . . . ?
C7 O4 C12 C11 58.0(6) . . . . ?
C7 C6 C5 F1 178.8(6) . . . . ?
C7 C6 C5 C4 -0.3(10) . . . . ?
C12 O4 C7 C6 154.2(6) . . . . ?
C12 O4 C7 C8 -27.1(8) . . . . ?
C11 N1 C1 C2 -178.6(5) . . . . ?
C11 N1 C8 C9 176.6(5) . . . . ?
C11 N1 C8 C7 -2.2(8) . . . . ?
C10 C2 C1 N1 -177.9(6) . . . . ?
O1S C1S C2S O2S 63.2(14) . . . . ?
O4S C4S C3S O4S -71(2) . . . 2_656 ?
O4S C4S C3S O3S 57(4) . . . . ?
O4S C4S C3S C4S -133(16) . . . 2_656 ?
O4S C4S C3S C3S -115(12) . . . 2_656 ?
O3S C4S C3S O4S 46(3) 2_656 . . 2_656 ?
O3S C4S C3S O3S 174(2) 2_656 . . . ?
O3S C4S C3S C4S -15(18) 2_656 . . 2_656 ?
O3S C4S C3S C3S 3(9) 2_656 . . 2_656 ?
C4S O3S C3S O4S -49(6) 2_656 . . 2_656 ?
C4S O3S C3S C4S 176(10) 2_656 . . . ?
C4S O3S C3S C3S 178(8) 2_656 . . 2_656 ?
C4S C4S C3S O4S 62(16) 2_656 . . 2_656 ?
C4S C4S C3S O3S -171(20) 2_656 . . . ?
C4S C4S C3S C3S 18(28) 2_656 . . 2_656 ?
C3S O4S C4S O3S -83(8) 2_656 . . 2_656 ?
C3S O4S C4S C4S 24(5) 2_656 . . 2_656 ?
C3S O4S C4S C3S 29(6) 2_656 . . . ?
C3S C4S C3S O4S 44(12) 2_656 . . 2_656 ?
C3S C4S C3S O3S 171(8) 2_656 . . . ?
C3S C4S C3S C4S -18(28) 2_656 . . 2_656 ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -3(2)
2 4(2)

####################################################################### 
# 
# 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_shelxl_sq
_database_code_depnum_ccdc_archive 'CCDC 1910841'
_audit_update_record             
;
2019-08-10 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_audit_creation_date             2019-08-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C18 H20 F N3 O4)'
_chemical_formula_sum            'C72 H80 F4 N12 O16'
_chemical_formula_weight         1445.48
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   26.067(5)
_cell_length_b                   9.2924(19)
_cell_length_c                   34.377(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.22(3)
_cell_angle_gamma                90
_cell_volume                     8304(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7447
_cell_measurement_temperature    128.15
_cell_measurement_theta_max      27.9263
_cell_measurement_theta_min      1.6341
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear(Rigaku, 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3040
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.1390
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            29443
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.188
_diffrn_ambient_temperature      128.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                8749
_reflns_number_total             14506
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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         0.483
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.145
_refine_ls_abs_structure_details 
;
 Flack x determined using 1619 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       0.0042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     950
_refine_ls_number_reflns         14506
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.1109
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1547P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2776
_refine_ls_wR_factor_ref         0.3122
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11A(H11A), C11C(H11C), C11B(H11B), C11D(H11D)
2.b Secondary CH2 refined with riding coordinates:
 C16A(H16A,H16B), C17A(H17A,H17B), C14A(H14A,H14B), C15A(H15A,H15B), C12A(H12A,
 H12B), C16C(H16C,H16D), C17C(H17C,H17D), C14C(H14C,H14D), C15C(H15C,H15D),
 C12C(H12C,H12D), C16B(H16E,H16F), C17B(H17E,H17F), C14B(H14E,H14F), C15B(H15E,
 H15F), C12B(H12E,H12F), C16D(H16G,H16H), C17D(H17G,H17H), C14D(H14G,H14H),
 C15D(H15G,H15H), C12D(H12G,H12H)
2.c Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C1A(H1AA), C4C(H4C), C1C(H1CA), C4B(H4B), C1B(H1BA), C4D(H4D),
 C1D(H1DA)
2.d Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C13A(H13A,H13B,H13C), C18C(H18D,H18E,H18F), C13C(H13D,
 H13E,H13F), C18B(H18G,H18H,H18I), C13B(H13G,H13H,H13I), C18D(H18J,H18K,H18L),
 C13D(H13J,H13K,H13L)
2.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1C(H1C), O1B(H1B), O1D(H1D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.5694(2) 0.4818(6) 0.77133(17) 0.0587(15) Uani 1 1 d . . . . .
O4A O 0.5066(3) 0.0791(7) 0.83715(17) 0.0500(16) Uani 1 1 d . . . . .
O3A O 0.4998(3) 0.1613(7) 0.66250(19) 0.0527(17) Uani 1 1 d . . . . .
O1A O 0.4599(3) -0.0562(8) 0.62598(19) 0.0602(19) Uani 1 1 d . . . . .
H1A H 0.4747 0.0227 0.6309 0.090 Uiso 1 1 calc GR . . . .
O2A O 0.4398(3) -0.2489(8) 0.6589(2) 0.069(2) Uani 1 1 d . . . . .
N3A N 0.5729(5) 0.4650(11) 0.9168(3) 0.080(3) Uani 1 1 d . . . . .
N2A N 0.5522(3) 0.3417(9) 0.8424(2) 0.052(2) Uani 1 1 d . . . . .
N1A N 0.4790(3) -0.0523(7) 0.7644(2) 0.0348(15) Uani 1 1 d . . . . .
C18A C 0.5903(7) 0.4626(18) 0.9593(3) 0.103(5) Uani 1 1 d . . . . .
H18A H 0.5946 0.3627 0.9681 0.154 Uiso 1 1 calc GR . . . .
H18B H 0.5644 0.5100 0.9742 0.154 Uiso 1 1 calc GR . . . .
H18C H 0.6231 0.5136 0.9635 0.154 Uiso 1 1 calc GR . . . .
C16A C 0.6161(5) 0.4302(15) 0.8927(3) 0.075(3) Uani 1 1 d . . . . .
H16A H 0.6299 0.3335 0.8997 0.090 Uiso 1 1 calc R . . . .
H16B H 0.6442 0.5012 0.8977 0.090 Uiso 1 1 calc R . . . .
C17A C 0.5966(4) 0.4336(11) 0.8490(3) 0.059(3) Uani 1 1 d . . . . .
H17A H 0.5875 0.5334 0.8413 0.071 Uiso 1 1 calc R . . . .
H17B H 0.6243 0.4004 0.8329 0.071 Uiso 1 1 calc R . . . .
C14A C 0.5101(4) 0.3816(12) 0.8665(3) 0.056(2) Uani 1 1 d . . . . .
H14A H 0.4810 0.3139 0.8617 0.067 Uiso 1 1 calc R . . . .
H14B H 0.4977 0.4798 0.8596 0.067 Uiso 1 1 calc R . . . .
C15A C 0.5303(5) 0.3765(14) 0.9099(3) 0.069(3) Uani 1 1 d . . . . .
H15A H 0.5027 0.4078 0.9263 0.083 Uiso 1 1 calc R . . . .
H15B H 0.5397 0.2763 0.9171 0.083 Uiso 1 1 calc R . . . .
C6A C 0.5379(3) 0.2830(10) 0.8057(3) 0.044(2) Uani 1 1 d . . . . .
C5A C 0.5465(3) 0.3510(9) 0.7689(3) 0.047(2) Uani 1 1 d . . . . .
C4A C 0.5339(4) 0.2911(10) 0.7340(3) 0.046(2) Uani 1 1 d . . . . .
H4A H 0.5412 0.3395 0.7107 0.055 Uiso 1 1 calc R . . . .
C9A C 0.5097(3) 0.1550(9) 0.7324(2) 0.0336(18) Uani 1 1 d . . . . .
C3A C 0.4945(3) 0.0928(11) 0.6947(3) 0.047(2) Uani 1 1 d . . . . .
C2A C 0.4731(3) -0.0474(8) 0.6950(3) 0.037(2) Uani 1 1 d . . . . .
C1A C 0.4676(3) -0.1141(10) 0.7297(3) 0.044(2) Uani 1 1 d . . . . .
H1AA H 0.4549 -0.2099 0.7292 0.053 Uiso 1 1 calc R . . . .
C8A C 0.5012(3) 0.0854(9) 0.7666(3) 0.039(2) Uani 1 1 d . . . . .
C7A C 0.5149(3) 0.1482(9) 0.8032(3) 0.038(2) Uani 1 1 d . . . . .
C12A C 0.4638(4) -0.0243(11) 0.8330(3) 0.058(3) Uani 1 1 d . . . . .
H12A H 0.4312 0.0275 0.8260 0.069 Uiso 1 1 calc R . . . .
H12B H 0.4604 -0.0740 0.8582 0.069 Uiso 1 1 calc R . . . .
C11A C 0.4733(4) -0.1325(10) 0.8021(3) 0.046(2) Uani 1 1 d . . . . .
H11A H 0.4421 -0.1952 0.7984 0.055 Uiso 1 1 calc R . . . .
C13A C 0.5184(4) -0.2268(11) 0.8116(3) 0.055(3) Uani 1 1 d . . . . .
H13A H 0.5493 -0.1674 0.8163 0.083 Uiso 1 1 calc GR . . . .
H13B H 0.5228 -0.2920 0.7897 0.083 Uiso 1 1 calc GR . . . .
H13C H 0.5129 -0.2832 0.8350 0.083 Uiso 1 1 calc GR . . . .
C10A C 0.4561(4) -0.1277(11) 0.6584(2) 0.047(2) Uani 1 1 d . . . . .
F1C F 0.5607(2) 0.5591(5) 0.67709(15) 0.0547(15) Uani 1 1 d . . . . .
O4C O 0.6006(3) 0.9683(6) 0.60366(17) 0.0485(16) Uani 1 1 d . . . . .
O3C O 0.6264(2) 0.9153(7) 0.77924(17) 0.0468(16) Uani 1 1 d . . . . .
O1C O 0.6618(3) 1.1428(7) 0.81157(18) 0.0526(17) Uani 1 1 d . . . . .
H1C H 0.6492 1.0600 0.8084 0.079 Uiso 1 1 calc GR . . . .
O2C O 0.6834(3) 1.3265(7) 0.7746(2) 0.0593(19) Uani 1 1 d . . . . .
N3C N 0.5837(4) 0.5807(11) 0.5297(2) 0.069(3) Uani 1 1 d . . . . .
N2C N 0.5674(3) 0.6805(8) 0.6061(2) 0.050(2) Uani 1 1 d . . . . .
N1C N 0.6335(3) 1.1102(7) 0.6727(2) 0.0405(17) Uani 1 1 d . . . . .
C18C C 0.6120(6) 0.563(2) 0.4942(3) 0.122(7) Uani 1 1 d . . . . .
H18D H 0.6119 0.4610 0.4867 0.184 Uiso 1 1 calc GR . . . .
H18E H 0.6476 0.5955 0.4995 0.184 Uiso 1 1 calc GR . . . .
H18F H 0.5953 0.6198 0.4729 0.184 Uiso 1 1 calc GR . . . .
C16C C 0.6163(4) 0.5258(12) 0.5631(3) 0.058(3) Uani 1 1 d . . . . .
H16C H 0.6480 0.5844 0.5669 0.069 Uiso 1 1 calc R . . . .
H16D H 0.6263 0.4251 0.5582 0.069 Uiso 1 1 calc R . . . .
C17C C 0.5854(4) 0.5333(11) 0.6012(2) 0.054(3) Uani 1 1 d . . . . .
H17C H 0.5558 0.4666 0.5986 0.065 Uiso 1 1 calc R . . . .
H17D H 0.6080 0.5042 0.6242 0.065 Uiso 1 1 calc R . . . .
C14C C 0.5382(3) 0.7357(10) 0.5718(3) 0.046(2) Uani 1 1 d . . . . .
H14C H 0.5300 0.8381 0.5762 0.055 Uiso 1 1 calc R . . . .
H14D H 0.5053 0.6823 0.5681 0.055 Uiso 1 1 calc R . . . .
C15C C 0.5661(4) 0.7231(10) 0.5358(3) 0.052(2) Uani 1 1 d . . . . .
H15C H 0.5430 0.7529 0.5131 0.063 Uiso 1 1 calc R . . . .
H15D H 0.5959 0.7894 0.5377 0.063 Uiso 1 1 calc R . . . .
C6C C 0.5813(4) 0.7592(10) 0.6397(2) 0.041(2) Uani 1 1 d . . . . .
C5C C 0.5795(4) 0.6939(10) 0.6767(3) 0.048(2) Uani 1 1 d . . . . .
C4C C 0.5934(3) 0.7594(9) 0.7106(2) 0.0366(19) Uani 1 1 d . . . . .
H4C H 0.5905 0.7100 0.7345 0.044 Uiso 1 1 calc R . . . .
C9C C 0.6123(3) 0.9008(10) 0.7108(2) 0.040(2) Uani 1 1 d . . . . .
C3C C 0.6283(3) 0.9746(9) 0.7465(2) 0.0330(18) Uani 1 1 d . . . . .
C2C C 0.6494(3) 1.1213(10) 0.7422(2) 0.039(2) Uani 1 1 d . . . . .
C1C C 0.6499(3) 1.1761(9) 0.7064(3) 0.039(2) Uani 1 1 d . . . . .
H1CA H 0.6630 1.2710 0.7044 0.047 Uiso 1 1 calc R . . . .
C8C C 0.6141(3) 0.9716(9) 0.6737(2) 0.0322(17) Uani 1 1 d . . . . .
C7C C 0.5980(3) 0.8992(9) 0.6392(2) 0.0355(18) Uani 1 1 d . . . . .
C12C C 0.5972(3) 1.1183(8) 0.6055(3) 0.043(2) Uani 1 1 d . . . . .
H12C H 0.5631 1.1462 0.6140 0.052 Uiso 1 1 calc R . . . .
H12D H 0.6007 1.1600 0.5794 0.052 Uiso 1 1 calc R . . . .
C11C C 0.6400(3) 1.1777(9) 0.6347(2) 0.0378(19) Uani 1 1 d . . . . .
H11C H 0.6353 1.2840 0.6372 0.045 Uiso 1 1 calc R . . . .
C13C C 0.6937(4) 1.1483(12) 0.6208(3) 0.059(3) Uani 1 1 d . . . . .
H13D H 0.6994 1.0443 0.6194 0.089 Uiso 1 1 calc GR . . . .
H13E H 0.7199 1.1912 0.6392 0.089 Uiso 1 1 calc GR . . . .
H13F H 0.6962 1.1908 0.5949 0.089 Uiso 1 1 calc GR . . . .
C10C C 0.6665(3) 1.2053(9) 0.7759(2) 0.0329(18) Uani 1 1 d . . . . .
F1B F 0.8155(2) 1.2433(6) 0.76183(17) 0.0623(16) Uani 1 1 d . . . . .
O4B O 0.7589(2) 0.8592(7) 0.83746(17) 0.0490(16) Uani 1 1 d . . . . .
O3B O 0.7518(2) 0.8785(7) 0.66111(16) 0.0467(15) Uani 1 1 d . . . . .
O1B O 0.7129(3) 0.6560(7) 0.63007(16) 0.0479(16) Uani 1 1 d . . . . .
H1B H 0.7296 0.7329 0.6333 0.072 Uiso 1 1 calc GR . . . .
O2B O 0.6889(3) 0.4736(7) 0.66802(19) 0.0576(18) Uani 1 1 d . . . . .
N3B N 0.8550(4) 1.1660(13) 0.9107(3) 0.074(3) Uani 1 1 d . . . . .
N2B N 0.8049(3) 1.1280(9) 0.8343(2) 0.054(2) Uani 1 1 d . . . . .
N1B N 0.7315(3) 0.7004(7) 0.7690(2) 0.0370(16) Uani 1 1 d . . . . .
C18B C 0.8856(6) 1.115(2) 0.9451(4) 0.112(6) Uani 1 1 d . . . . .
H18G H 0.9219 1.1381 0.9426 0.168 Uiso 1 1 calc GR . . . .
H18H H 0.8815 1.0110 0.9476 0.168 Uiso 1 1 calc GR . . . .
H18I H 0.8739 1.1630 0.9683 0.168 Uiso 1 1 calc GR . . . .
C16B C 0.8821(4) 1.1457(13) 0.8765(4) 0.071(3) Uani 1 1 d . . . . .
H16E H 0.8900 1.0421 0.8741 0.085 Uiso 1 1 calc R . . . .
H16F H 0.9151 1.1981 0.8799 0.085 Uiso 1 1 calc R . . . .
C17B C 0.8532(4) 1.1961(11) 0.8385(3) 0.055(3) Uani 1 1 d . . . . .
H17E H 0.8486 1.3018 0.8391 0.066 Uiso 1 1 calc R . . . .
H17F H 0.8733 1.1719 0.8161 0.066 Uiso 1 1 calc R . . . .
C14B C 0.7744(4) 1.1425(12) 0.8679(3) 0.057(3) Uani 1 1 d . . . . .
H14E H 0.7420 1.0878 0.8633 0.069 Uiso 1 1 calc R . . . .
H14F H 0.7657 1.2450 0.8717 0.069 Uiso 1 1 calc R . . . .
C15B C 0.8050(5) 1.0851(15) 0.9044(3) 0.075(3) Uani 1 1 d . . . . .
H15E H 0.7847 1.0971 0.9274 0.090 Uiso 1 1 calc R . . . .
H15F H 0.8120 0.9812 0.9012 0.090 Uiso 1 1 calc R . . . .
C6B C 0.7879(4) 1.0533(10) 0.8002(3) 0.046(2) Uani 1 1 d . . . . .
C5B C 0.7944(3) 1.1085(8) 0.7630(3) 0.041(2) Uani 1 1 d . . . . .
C4B C 0.7803(3) 1.0411(9) 0.7291(2) 0.0379(19) Uani 1 1 d . . . . .
H4B H 0.7846 1.0872 0.7049 0.045 Uiso 1 1 calc R . . . .
C9B C 0.7596(3) 0.9037(8) 0.7301(3) 0.0339(18) Uani 1 1 d . . . . .
C3B C 0.7445(3) 0.8262(10) 0.6945(3) 0.042(2) Uani 1 1 d . . . . .
C2B C 0.7232(3) 0.6856(9) 0.6993(2) 0.0355(19) Uani 1 1 d . . . . .
C1B C 0.7184(3) 0.6276(10) 0.7354(2) 0.039(2) Uani 1 1 d . . . . .
H1BA H 0.7053 0.5325 0.7371 0.047 Uiso 1 1 calc R . . . .
C8B C 0.7511(3) 0.8427(8) 0.7670(3) 0.0374(19) Uani 1 1 d . . . . .
C7B C 0.7646(3) 0.9132(9) 0.8013(2) 0.0356(19) Uani 1 1 d . . . . .
C12B C 0.7180(4) 0.7479(10) 0.8362(3) 0.054(2) Uani 1 1 d . . . . .
H12E H 0.7172 0.7030 0.8623 0.065 Uiso 1 1 calc R . . . .
H12F H 0.6842 0.7937 0.8296 0.065 Uiso 1 1 calc R . . . .
C11B C 0.7272(4) 0.6356(11) 0.8070(2) 0.049(2) Uani 1 1 d . . . . .
H11B H 0.6968 0.5699 0.8050 0.058 Uiso 1 1 calc R . . . .
C13B C 0.7753(4) 0.5445(12) 0.8196(3) 0.060(3) Uani 1 1 d . . . . .
H13G H 0.8048 0.6083 0.8255 0.090 Uiso 1 1 calc GR . . . .
H13H H 0.7828 0.4790 0.7984 0.090 Uiso 1 1 calc GR . . . .
H13I H 0.7688 0.4885 0.8429 0.090 Uiso 1 1 calc GR . . . .
C10B C 0.7078(4) 0.5938(12) 0.6647(3) 0.058(3) Uani 1 1 d . . . . .
F1D F 0.8142(2) 0.3230(5) 0.64966(18) 0.0612(16) Uani 1 1 d . . . . .
O4D O 0.8493(2) 0.7678(8) 0.59062(17) 0.0485(16) Uani 1 1 d . . . . .
O3D O 0.8712(3) 0.6414(7) 0.76349(17) 0.0547(18) Uani 1 1 d . . . . .
O1D O 0.9053(3) 0.8548(8) 0.80289(18) 0.063(2) Uani 1 1 d . . . . .
H1D H 0.9000 0.7685 0.7966 0.094 Uiso 1 1 calc GR . . . .
O2D O 0.9305(3) 1.0541(8) 0.7728(2) 0.0575(18) Uani 1 1 d . . . . .
N3D N 0.7928(3) 0.3851(10) 0.5055(2) 0.059(2) Uani 1 1 d . . . . .
N2D N 0.8171(3) 0.4967(9) 0.5810(2) 0.053(2) Uani 1 1 d . . . . .
N1D N 0.8841(3) 0.8826(8) 0.6643(2) 0.0427(17) Uani 1 1 d . . . . .
C18D C 0.7691(5) 0.3941(14) 0.4649(3) 0.069(3) Uani 1 1 d . . . . .
H18J H 0.7491 0.4833 0.4617 0.104 Uiso 1 1 calc GR . . . .
H18K H 0.7463 0.3114 0.4596 0.104 Uiso 1 1 calc GR . . . .
H18L H 0.7962 0.3937 0.4466 0.104 Uiso 1 1 calc GR . . . .
C16D C 0.7535(4) 0.4038(11) 0.5330(3) 0.058(3) Uani 1 1 d . . . . .
H16G H 0.7262 0.3309 0.5278 0.070 Uiso 1 1 calc R . . . .
H16H H 0.7377 0.5003 0.5295 0.070 Uiso 1 1 calc R . . . .
C17D C 0.7762(4) 0.3885(14) 0.5743(3) 0.066(3) Uani 1 1 d . . . . .
H17G H 0.7492 0.4036 0.5927 0.079 Uiso 1 1 calc R . . . .
H17H H 0.7905 0.2906 0.5785 0.079 Uiso 1 1 calc R . . . .
C14D C 0.8561(4) 0.4826(14) 0.5534(3) 0.062(3) Uani 1 1 d . . . . .
H14G H 0.8736 0.3884 0.5570 0.074 Uiso 1 1 calc R . . . .
H14H H 0.8822 0.5594 0.5580 0.074 Uiso 1 1 calc R . . . .
C15D C 0.8307(4) 0.4943(12) 0.5110(3) 0.057(3) Uani 1 1 d . . . . .
H15G H 0.8147 0.5902 0.5069 0.068 Uiso 1 1 calc R . . . .
H15H H 0.8571 0.4822 0.4919 0.068 Uiso 1 1 calc R . . . .
C6D C 0.8311(3) 0.5427(10) 0.6186(3) 0.044(2) Uani 1 1 d . . . . .
C5D C 0.8298(4) 0.4607(12) 0.6528(3) 0.051(2) Uani 1 1 d . . . . .
C4D C 0.8422(3) 0.5106(9) 0.6897(3) 0.039(2) Uani 1 1 d . . . . .
H4D H 0.8379 0.4515 0.7117 0.047 Uiso 1 1 calc R . . . .
C9D C 0.8615(3) 0.6511(9) 0.6944(3) 0.040(2) Uani 1 1 d . . . . .
C3D C 0.8755(3) 0.7146(10) 0.7330(2) 0.040(2) Uani 1 1 d . . . . .
C2D C 0.8960(3) 0.8539(9) 0.7332(2) 0.040(2) Uani 1 1 d . . . . .
C1D C 0.8994(3) 0.9307(9) 0.6991(2) 0.039(2) Uani 1 1 d . . . . .
H1DA H 0.9139 1.0245 0.7009 0.047 Uiso 1 1 calc R . . . .
C8D C 0.8662(3) 0.7373(9) 0.6603(2) 0.0375(19) Uani 1 1 d . . . . .
C7D C 0.8495(4) 0.6875(10) 0.6233(3) 0.043(2) Uani 1 1 d . . . . .
C12D C 0.8455(4) 0.9228(11) 0.5996(3) 0.054(3) Uani 1 1 d . . . . .
H12G H 0.8127 0.9431 0.6112 0.064 Uiso 1 1 calc R . . . .
H12H H 0.8465 0.9800 0.5753 0.064 Uiso 1 1 calc R . . . .
C11D C 0.8908(3) 0.9642(10) 0.6283(3) 0.044(2) Uani 1 1 d . . . . .
H11D H 0.8875 1.0688 0.6344 0.053 Uiso 1 1 calc R . . . .
C13D C 0.9440(4) 0.9406(11) 0.6135(3) 0.052(2) Uani 1 1 d . . . . .
H13J H 0.9505 0.8371 0.6113 0.077 Uiso 1 1 calc GR . . . .
H13K H 0.9702 0.9837 0.6318 0.077 Uiso 1 1 calc GR . . . .
H13L H 0.9454 0.9857 0.5878 0.077 Uiso 1 1 calc GR . . . .
C10D C 0.9131(3) 0.9317(11) 0.7712(2) 0.044(2) 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
F1A C5A 1.354(10) . ?
O4A C7A 1.364(10) . ?
O4A C12A 1.472(11) . ?
O3A C3A 1.291(11) . ?
O1A H1A 0.8400 . ?
O1A C10A 1.307(11) . ?
O2A C10A 1.204(12) . ?
N3A C18A 1.498(14) . ?
N3A C16A 1.483(16) . ?
N3A C15A 1.389(15) . ?
N2A C17A 1.444(13) . ?
N2A C14A 1.470(13) . ?
N2A C6A 1.398(11) . ?
N1A C1A 1.337(11) . ?
N1A C8A 1.405(11) . ?
N1A C11A 1.514(11) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16A C17A 1.550(14) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C14A C15A 1.545(12) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C6A C5A 1.445(14) . ?
C6A C7A 1.389(12) . ?
C5A C4A 1.344(13) . ?
C4A H4A 0.9500 . ?
C4A C9A 1.412(13) . ?
C9A C3A 1.450(12) . ?
C9A C8A 1.372(12) . ?
C3A C2A 1.417(13) . ?
C2A C1A 1.362(13) . ?
C2A C10A 1.501(11) . ?
C1A H1AA 0.9500 . ?
C8A C7A 1.409(12) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C12A C11A 1.496(13) . ?
C11A H11A 1.0000 . ?
C11A C13A 1.483(13) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
F1C C5C 1.346(10) . ?
O4C C7C 1.386(10) . ?
O4C C12C 1.398(10) . ?
O3C C3C 1.258(10) . ?
O1C H1C 0.8400 . ?
O1C C10C 1.371(10) . ?
O2C C10C 1.211(10) . ?
N3C C18C 1.480(16) . ?
N3C C16C 1.469(13) . ?
N3C C15C 1.422(14) . ?
N2C C17C 1.460(13) . ?
N2C C14C 1.448(11) . ?
N2C C6C 1.394(11) . ?
N1C C1C 1.351(11) . ?
N1C C8C 1.386(11) . ?
N1C C11C 1.471(11) . ?
C18C H18D 0.9800 . ?
C18C H18E 0.9800 . ?
C18C H18F 0.9800 . ?
C16C H16C 0.9900 . ?
C16C H16D 0.9900 . ?
C16C C17C 1.585(14) . ?
C17C H17C 0.9900 . ?
C17C H17D 0.9900 . ?
C14C H14C 0.9900 . ?
C14C H14D 0.9900 . ?
C14C C15C 1.485(14) . ?
C15C H15C 0.9900 . ?
C15C H15D 0.9900 . ?
C6C C5C 1.411(12) . ?
C6C C7C 1.373(12) . ?
C5C C4C 1.341(13) . ?
C4C H4C 0.9500 . ?
C4C C9C 1.403(13) . ?
C9C C3C 1.442(11) . ?
C9C C8C 1.437(11) . ?
C3C C2C 1.482(12) . ?
C2C C1C 1.332(12) . ?
C2C C10C 1.440(12) . ?
C1C H1CA 0.9500 . ?
C8C C7C 1.400(11) . ?
C12C H12C 0.9900 . ?
C12C H12D 0.9900 . ?
C12C C11C 1.546(12) . ?
C11C H11C 1.0000 . ?
C11C C13C 1.536(13) . ?
C13C H13D 0.9800 . ?
C13C H13E 0.9800 . ?
C13C H13F 0.9800 . ?
F1B C5B 1.370(10) . ?
O4B C7B 1.359(9) . ?
O4B C12B 1.483(11) . ?
O3B C3B 1.273(11) . ?
O1B H1B 0.8400 . ?
O1B C10B 1.338(12) . ?
O2B C10B 1.229(13) . ?
N3B C18B 1.455(15) . ?
N3B C16B 1.424(16) . ?
N3B C15B 1.507(15) . ?
N2B C17B 1.406(13) . ?
N2B C14B 1.454(12) . ?
N2B C6B 1.405(12) . ?
N1B C1B 1.362(10) . ?
N1B C8B 1.421(10) . ?
N1B C11B 1.449(11) . ?
C18B H18G 0.9800 . ?
C18B H18H 0.9800 . ?
C18B H18I 0.9800 . ?
C16B H16E 0.9900 . ?
C16B H16F 0.9900 . ?
C16B C17B 1.532(14) . ?
C17B H17E 0.9900 . ?
C17B H17F 0.9900 . ?
C14B H14E 0.9900 . ?
C14B H14F 0.9900 . ?
C14B C15B 1.534(15) . ?
C15B H15E 0.9900 . ?
C15B H15F 0.9900 . ?
C6B C5B 1.399(13) . ?
C6B C7B 1.439(12) . ?
C5B C4B 1.351(12) . ?
C4B H4B 0.9500 . ?
C4B C9B 1.387(11) . ?
C9B C3B 1.450(12) . ?
C9B C8B 1.421(12) . ?
C3B C2B 1.436(13) . ?
C2B C1B 1.366(12) . ?
C2B C10B 1.495(13) . ?
C1B H1BA 0.9500 . ?
C8B C7B 1.372(11) . ?
C12B H12E 0.9900 . ?
C12B H12F 0.9900 . ?
C12B C11B 1.481(14) . ?
C11B H11B 1.0000 . ?
C11B C13B 1.548(14) . ?
C13B H13G 0.9800 . ?
C13B H13H 0.9800 . ?
C13B H13I 0.9800 . ?
F1D C5D 1.345(12) . ?
O4D C7D 1.349(11) . ?
O4D C12D 1.477(13) . ?
O3D C3D 1.261(11) . ?
O1D H1D 0.8400 . ?
O1D C10D 1.332(12) . ?
O2D C10D 1.225(12) . ?
N3D C18D 1.488(12) . ?
N3D C16D 1.455(14) . ?
N3D C15D 1.418(13) . ?
N2D C17D 1.472(12) . ?
N2D C14D 1.447(12) . ?
N2D C6D 1.384(12) . ?
N1D C1D 1.310(11) . ?
N1D C8D 1.431(11) . ?
N1D C11D 1.474(11) . ?
C18D H18J 0.9800 . ?
C18D H18K 0.9800 . ?
C18D H18L 0.9800 . ?
C16D H16G 0.9900 . ?
C16D H16H 0.9900 . ?
C16D C17D 1.502(14) . ?
C17D H17G 0.9900 . ?
C17D H17H 0.9900 . ?
C14D H14G 0.9900 . ?
C14D H14H 0.9900 . ?
C14D C15D 1.561(12) . ?
C15D H15G 0.9900 . ?
C15D H15H 0.9900 . ?
C6D C5D 1.404(13) . ?
C6D C7D 1.433(13) . ?
C5D C4D 1.368(13) . ?
C4D H4D 0.9500 . ?
C4D C9D 1.404(12) . ?
C9D C3D 1.474(11) . ?
C9D C8D 1.432(12) . ?
C3D C2D 1.401(12) . ?
C2D C1D 1.382(12) . ?
C2D C10D 1.528(11) . ?
C1D H1DA 0.9500 . ?
C8D C7D 1.392(12) . ?
C12D H12G 0.9900 . ?
C12D H12H 0.9900 . ?
C12D C11D 1.531(12) . ?
C11D H11D 1.0000 . ?
C11D C13D 1.527(13) . ?
C13D H13J 0.9800 . ?
C13D H13K 0.9800 . ?
C13D H13L 0.9800 . ?

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
C7A O4A C12A 113.1(7) . . ?
C10A O1A H1A 109.5 . . ?
C16A N3A C18A 110.8(11) . . ?
C15A N3A C18A 109.9(11) . . ?
C15A N3A C16A 113.9(10) . . ?
C17A N2A C14A 112.6(8) . . ?
C6A N2A C17A 122.0(9) . . ?
C6A N2A C14A 116.6(7) . . ?
C1A N1A C8A 120.2(7) . . ?
C1A N1A C11A 121.6(7) . . ?
C8A N1A C11A 117.9(7) . . ?
N3A C18A H18A 109.5 . . ?
N3A C18A H18B 109.5 . . ?
N3A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N3A C16A H16A 109.8 . . ?
N3A C16A H16B 109.8 . . ?
N3A C16A C17A 109.2(9) . . ?
H16A C16A H16B 108.3 . . ?
C17A C16A H16A 109.8 . . ?
C17A C16A H16B 109.8 . . ?
N2A C17A C16A 110.1(10) . . ?
N2A C17A H17A 109.6 . . ?
N2A C17A H17B 109.6 . . ?
C16A C17A H17A 109.6 . . ?
C16A C17A H17B 109.6 . . ?
H17A C17A H17B 108.1 . . ?
N2A C14A H14A 109.9 . . ?
N2A C14A H14B 109.9 . . ?
N2A C14A C15A 108.8(8) . . ?
H14A C14A H14B 108.3 . . ?
C15A C14A H14A 109.9 . . ?
C15A C14A H14B 109.9 . . ?
N3A C15A C14A 111.1(10) . . ?
N3A C15A H15A 109.4 . . ?
N3A C15A H15B 109.4 . . ?
C14A C15A H15A 109.4 . . ?
C14A C15A H15B 109.4 . . ?
H15A C15A H15B 108.0 . . ?
N2A C6A C5A 124.7(8) . . ?
C7A C6A N2A 119.5(9) . . ?
C7A C6A C5A 115.7(8) . . ?
F1A C5A C6A 115.8(8) . . ?
C4A C5A F1A 120.2(9) . . ?
C4A C5A C6A 123.9(8) . . ?
C5A C4A H4A 120.6 . . ?
C5A C4A C9A 118.9(9) . . ?
C9A C4A H4A 120.6 . . ?
C4A C9A C3A 118.8(8) . . ?
C8A C9A C4A 119.3(8) . . ?
C8A C9A C3A 121.8(8) . . ?
O3A C3A C9A 122.1(8) . . ?
O3A C3A C2A 121.7(9) . . ?
C2A C3A C9A 116.2(8) . . ?
C3A C2A C10A 122.9(8) . . ?
C1A C2A C3A 119.5(8) . . ?
C1A C2A C10A 117.6(8) . . ?
N1A C1A C2A 123.8(8) . . ?
N1A C1A H1AA 118.1 . . ?
C2A C1A H1AA 118.1 . . ?
N1A C8A C7A 120.1(8) . . ?
C9A C8A N1A 118.4(8) . . ?
C9A C8A C7A 121.5(8) . . ?
O4A C7A C6A 117.8(8) . . ?
O4A C7A C8A 121.6(7) . . ?
C6A C7A C8A 120.6(8) . . ?
O4A C12A H12A 109.7 . . ?
O4A C12A H12B 109.7 . . ?
O4A C12A C11A 110.0(8) . . ?
H12A C12A H12B 108.2 . . ?
C11A C12A H12A 109.7 . . ?
C11A C12A H12B 109.7 . . ?
N1A C11A H11A 107.9 . . ?
C12A C11A N1A 108.0(8) . . ?
C12A C11A H11A 107.9 . . ?
C13A C11A N1A 110.6(8) . . ?
C13A C11A C12A 114.3(8) . . ?
C13A C11A H11A 107.9 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O1A C10A C2A 115.1(8) . . ?
O2A C10A O1A 122.5(8) . . ?
O2A C10A C2A 122.4(9) . . ?
C7C O4C C12C 114.4(7) . . ?
C10C O1C H1C 109.5 . . ?
C16C N3C C18C 108.2(9) . . ?
C15C N3C C18C 114.4(10) . . ?
C15C N3C C16C 112.4(9) . . ?
C14C N2C C17C 113.1(7) . . ?
C6C N2C C17C 121.4(7) . . ?
C6C N2C C14C 125.3(7) . . ?
C1C N1C C8C 119.5(7) . . ?
C1C N1C C11C 121.3(7) . . ?
C8C N1C C11C 119.0(7) . . ?
N3C C18C H18D 109.5 . . ?
N3C C18C H18E 109.5 . . ?
N3C C18C H18F 109.5 . . ?
H18D C18C H18E 109.5 . . ?
H18D C18C H18F 109.5 . . ?
H18E C18C H18F 109.5 . . ?
N3C C16C H16C 109.8 . . ?
N3C C16C H16D 109.8 . . ?
N3C C16C C17C 109.3(8) . . ?
H16C C16C H16D 108.3 . . ?
C17C C16C H16C 109.8 . . ?
C17C C16C H16D 109.8 . . ?
N2C C17C C16C 108.9(8) . . ?
N2C C17C H17C 109.9 . . ?
N2C C17C H17D 109.9 . . ?
C16C C17C H17C 109.9 . . ?
C16C C17C H17D 109.9 . . ?
H17C C17C H17D 108.3 . . ?
N2C C14C H14C 109.0 . . ?
N2C C14C H14D 109.0 . . ?
N2C C14C C15C 112.9(8) . . ?
H14C C14C H14D 107.8 . . ?
C15C C14C H14C 109.0 . . ?
C15C C14C H14D 109.0 . . ?
N3C C15C C14C 112.3(8) . . ?
N3C C15C H15C 109.1 . . ?
N3C C15C H15D 109.1 . . ?
C14C C15C H15C 109.1 . . ?
C14C C15C H15D 109.1 . . ?
H15C C15C H15D 107.9 . . ?
N2C C6C C5C 119.9(8) . . ?
C7C C6C N2C 123.3(8) . . ?
C7C C6C C5C 116.8(8) . . ?
F1C C5C C6C 116.4(9) . . ?
C4C C5C F1C 119.3(8) . . ?
C4C C5C C6C 124.2(8) . . ?
C5C C4C H4C 120.0 . . ?
C5C C4C C9C 120.0(8) . . ?
C9C C4C H4C 120.0 . . ?
C4C C9C C3C 121.9(8) . . ?
C4C C9C C8C 117.3(7) . . ?
C8C C9C C3C 120.8(8) . . ?
O3C C3C C9C 121.8(8) . . ?
O3C C3C C2C 122.2(8) . . ?
C9C C3C C2C 116.0(7) . . ?
C1C C2C C3C 118.2(8) . . ?
C1C C2C C10C 120.8(8) . . ?
C10C C2C C3C 120.8(7) . . ?
N1C C1C H1CA 116.8 . . ?
C2C C1C N1C 126.5(8) . . ?
C2C C1C H1CA 116.8 . . ?
N1C C8C C9C 118.9(7) . . ?
N1C C8C C7C 120.8(7) . . ?
C7C C8C C9C 120.3(7) . . ?
O4C C7C C8C 119.6(7) . . ?
C6C C7C O4C 119.1(7) . . ?
C6C C7C C8C 121.2(8) . . ?
O4C C12C H12C 109.7 . . ?
O4C C12C H12D 109.7 . . ?
O4C C12C C11C 109.9(7) . . ?
H12C C12C H12D 108.2 . . ?
C11C C12C H12C 109.7 . . ?
C11C C12C H12D 109.7 . . ?
N1C C11C C12C 107.4(7) . . ?
N1C C11C H11C 108.8 . . ?
N1C C11C C13C 111.5(7) . . ?
C12C C11C H11C 108.8 . . ?
C13C C11C C12C 111.6(8) . . ?
C13C C11C H11C 108.8 . . ?
C11C C13C H13D 109.5 . . ?
C11C C13C H13E 109.5 . . ?
C11C C13C H13F 109.5 . . ?
H13D C13C H13E 109.5 . . ?
H13D C13C H13F 109.5 . . ?
H13E C13C H13F 109.5 . . ?
O1C C10C C2C 116.6(7) . . ?
O2C C10C O1C 118.9(8) . . ?
O2C C10C C2C 124.5(8) . . ?
C7B O4B C12B 110.9(7) . . ?
C10B O1B H1B 109.5 . . ?
C18B N3B C15B 111.8(11) . . ?
C16B N3B C18B 110.7(10) . . ?
C16B N3B C15B 106.9(9) . . ?
C17B N2B C14B 114.4(8) . . ?
C6B N2B C17B 122.2(8) . . ?
C6B N2B C14B 123.3(8) . . ?
C1B N1B C8B 119.3(7) . . ?
C1B N1B C11B 121.8(7) . . ?
C8B N1B C11B 118.9(8) . . ?
N3B C18B H18G 109.5 . . ?
N3B C18B H18H 109.5 . . ?
N3B C18B H18I 109.5 . . ?
H18G C18B H18H 109.5 . . ?
H18G C18B H18I 109.5 . . ?
H18H C18B H18I 109.5 . . ?
N3B C16B H16E 108.6 . . ?
N3B C16B H16F 108.6 . . ?
N3B C16B C17B 114.8(10) . . ?
H16E C16B H16F 107.5 . . ?
C17B C16B H16E 108.6 . . ?
C17B C16B H16F 108.6 . . ?
N2B C17B C16B 109.3(9) . . ?
N2B C17B H17E 109.8 . . ?
N2B C17B H17F 109.8 . . ?
C16B C17B H17E 109.8 . . ?
C16B C17B H17F 109.8 . . ?
H17E C17B H17F 108.3 . . ?
N2B C14B H14E 109.7 . . ?
N2B C14B H14F 109.7 . . ?
N2B C14B C15B 109.6(9) . . ?
H14E C14B H14F 108.2 . . ?
C15B C14B H14E 109.7 . . ?
C15B C14B H14F 109.7 . . ?
N3B C15B C14B 109.6(9) . . ?
N3B C15B H15E 109.7 . . ?
N3B C15B H15F 109.7 . . ?
C14B C15B H15E 109.7 . . ?
C14B C15B H15F 109.7 . . ?
H15E C15B H15F 108.2 . . ?
N2B C6B C7B 122.3(8) . . ?
C5B C6B N2B 121.9(8) . . ?
C5B C6B C7B 115.7(8) . . ?
F1B C5B C6B 116.0(8) . . ?
C4B C5B F1B 118.8(8) . . ?
C4B C5B C6B 125.2(8) . . ?
C5B C4B H4B 120.5 . . ?
C5B C4B C9B 119.1(8) . . ?
C9B C4B H4B 120.5 . . ?
C4B C9B C3B 121.1(8) . . ?
C4B C9B C8B 118.5(7) . . ?
C8B C9B C3B 120.3(7) . . ?
O3B C3B C9B 121.5(8) . . ?
O3B C3B C2B 122.4(8) . . ?
C2B C3B C9B 116.0(8) . . ?
C3B C2B C10B 120.8(8) . . ?
C1B C2B C3B 121.7(7) . . ?
C1B C2B C10B 117.4(8) . . ?
N1B C1B C2B 122.7(8) . . ?
N1B C1B H1BA 118.6 . . ?
C2B C1B H1BA 118.6 . . ?
C9B C8B N1B 119.7(7) . . ?
C7B C8B N1B 118.2(8) . . ?
C7B C8B C9B 122.0(7) . . ?
O4B C7B C6B 115.5(7) . . ?
O4B C7B C8B 124.9(8) . . ?
C8B C7B C6B 119.5(7) . . ?
O4B C12B H12E 109.4 . . ?
O4B C12B H12F 109.4 . . ?
H12E C12B H12F 108.0 . . ?
C11B C12B O4B 111.0(8) . . ?
C11B C12B H12E 109.4 . . ?
C11B C12B H12F 109.4 . . ?
N1B C11B C12B 110.2(8) . . ?
N1B C11B H11B 107.9 . . ?
N1B C11B C13B 111.4(8) . . ?
C12B C11B H11B 107.9 . . ?
C12B C11B C13B 111.3(8) . . ?
C13B C11B H11B 107.9 . . ?
C11B C13B H13G 109.5 . . ?
C11B C13B H13H 109.5 . . ?
C11B C13B H13I 109.5 . . ?
H13G C13B H13H 109.5 . . ?
H13G C13B H13I 109.5 . . ?
H13H C13B H13I 109.5 . . ?
O1B C10B C2B 115.0(9) . . ?
O2B C10B O1B 122.8(10) . . ?
O2B C10B C2B 122.0(9) . . ?
C7D O4D C12D 111.3(7) . . ?
C10D O1D H1D 109.5 . . ?
C16D N3D C18D 109.8(8) . . ?
C15D N3D C18D 108.8(8) . . ?
C15D N3D C16D 110.2(8) . . ?
C14D N2D C17D 111.9(8) . . ?
C6D N2D C17D 119.7(8) . . ?
C6D N2D C14D 119.3(8) . . ?
C1D N1D C8D 119.1(7) . . ?
C1D N1D C11D 122.9(7) . . ?
C8D N1D C11D 117.5(7) . . ?
N3D C18D H18J 109.5 . . ?
N3D C18D H18K 109.5 . . ?
N3D C18D H18L 109.5 . . ?
H18J C18D H18K 109.5 . . ?
H18J C18D H18L 109.5 . . ?
H18K C18D H18L 109.5 . . ?
N3D C16D H16G 109.5 . . ?
N3D C16D H16H 109.5 . . ?
N3D C16D C17D 110.9(9) . . ?
H16G C16D H16H 108.1 . . ?
C17D C16D H16G 109.5 . . ?
C17D C16D H16H 109.5 . . ?
N2D C17D C16D 108.2(9) . . ?
N2D C17D H17G 110.1 . . ?
N2D C17D H17H 110.1 . . ?
C16D C17D H17G 110.1 . . ?
C16D C17D H17H 110.1 . . ?
H17G C17D H17H 108.4 . . ?
N2D C14D H14G 109.8 . . ?
N2D C14D H14H 109.8 . . ?
N2D C14D C15D 109.5(8) . . ?
H14G C14D H14H 108.2 . . ?
C15D C14D H14G 109.8 . . ?
C15D C14D H14H 109.8 . . ?
N3D C15D C14D 108.5(9) . . ?
N3D C15D H15G 110.0 . . ?
N3D C15D H15H 110.0 . . ?
C14D C15D H15G 110.0 . . ?
C14D C15D H15H 110.0 . . ?
H15G C15D H15H 108.4 . . ?
N2D C6D C5D 126.4(9) . . ?
N2D C6D C7D 117.3(8) . . ?
C5D C6D C7D 116.2(9) . . ?
F1D C5D C6D 118.4(9) . . ?
F1D C5D C4D 116.5(8) . . ?
C4D C5D C6D 125.1(9) . . ?
C5D C4D H4D 120.7 . . ?
C5D C4D C9D 118.7(8) . . ?
C9D C4D H4D 120.7 . . ?
C4D C9D C3D 122.5(8) . . ?
C4D C9D C8D 118.6(8) . . ?
C8D C9D C3D 118.9(8) . . ?
O3D C3D C9D 120.2(8) . . ?
O3D C3D C2D 123.5(8) . . ?
C2D C3D C9D 116.3(8) . . ?
C3D C2D C10D 121.9(8) . . ?
C1D C2D C3D 121.4(8) . . ?
C1D C2D C10D 116.6(8) . . ?
N1D C1D C2D 124.3(8) . . ?
N1D C1D H1DA 117.8 . . ?
C2D C1D H1DA 117.8 . . ?
N1D C8D C9D 119.7(7) . . ?
C7D C8D N1D 118.7(8) . . ?
C7D C8D C9D 121.4(8) . . ?
O4D C7D C6D 116.3(7) . . ?
O4D C7D C8D 123.9(8) . . ?
C8D C7D C6D 119.7(8) . . ?
O4D C12D H12G 110.0 . . ?
O4D C12D H12H 110.0 . . ?
O4D C12D C11D 108.6(8) . . ?
H12G C12D H12H 108.4 . . ?
C11D C12D H12G 110.0 . . ?
C11D C12D H12H 110.0 . . ?
N1D C11D C12D 106.2(7) . . ?
N1D C11D H11D 107.8 . . ?
N1D C11D C13D 111.9(7) . . ?
C12D C11D H11D 107.8 . . ?
C13D C11D C12D 115.1(8) . . ?
C13D C11D H11D 107.8 . . ?
C11D C13D H13J 109.5 . . ?
C11D C13D H13K 109.5 . . ?
C11D C13D H13L 109.5 . . ?
H13J C13D H13K 109.5 . . ?
H13J C13D H13L 109.5 . . ?
H13K C13D H13L 109.5 . . ?
O1D C10D C2D 113.2(9) . . ?
O2D C10D O1D 122.5(8) . . ?
O2D C10D C2D 124.3(8) . . ?

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
F1A C5A C4A C9A -179.5(7) . . . . ?
O4A C12A C11A N1A -58.5(10) . . . . ?
O4A C12A C11A C13A 65.1(11) . . . . ?
O3A C3A C2A C1A -178.9(8) . . . . ?
O3A C3A C2A C10A 1.2(14) . . . . ?
N3A C16A C17A N2A -53.3(13) . . . . ?
N2A C14A C15A N3A 56.4(13) . . . . ?
N2A C6A C5A F1A -1.0(13) . . . . ?
N2A C6A C5A C4A 178.0(9) . . . . ?
N2A C6A C7A O4A 0.7(12) . . . . ?
N2A C6A C7A C8A -178.7(8) . . . . ?
N1A C8A C7A O4A -0.8(12) . . . . ?
N1A C8A C7A C6A 178.6(8) . . . . ?
C18A N3A C16A C17A 179.9(11) . . . . ?
C18A N3A C15A C14A 177.7(11) . . . . ?
C16A N3A C15A C14A -57.3(13) . . . . ?
C17A N2A C14A C15A -57.4(11) . . . . ?
C17A N2A C6A C5A -31.2(14) . . . . ?
C17A N2A C6A C7A 147.1(9) . . . . ?
C14A N2A C17A C16A 57.3(11) . . . . ?
C14A N2A C6A C5A 113.9(10) . . . . ?
C14A N2A C6A C7A -67.7(12) . . . . ?
C15A N3A C16A C17A 55.4(14) . . . . ?
C6A N2A C17A C16A -156.3(10) . . . . ?
C6A N2A C14A C15A 154.3(9) . . . . ?
C6A C5A C4A C9A 1.5(14) . . . . ?
C5A C6A C7A O4A 179.3(7) . . . . ?
C5A C6A C7A C8A -0.1(12) . . . . ?
C5A C4A C9A C3A 177.8(8) . . . . ?
C5A C4A C9A C8A -2.0(13) . . . . ?
C4A C9A C3A O3A -3.9(13) . . . . ?
C4A C9A C3A C2A 176.5(8) . . . . ?
C4A C9A C8A N1A -177.5(7) . . . . ?
C4A C9A C8A C7A 1.6(12) . . . . ?
C9A C3A C2A C1A 0.7(12) . . . . ?
C9A C3A C2A C10A -179.2(8) . . . . ?
C9A C8A C7A O4A -179.8(7) . . . . ?
C9A C8A C7A C6A -0.5(13) . . . . ?
C3A C9A C8A N1A 2.6(12) . . . . ?
C3A C9A C8A C7A -178.3(7) . . . . ?
C3A C2A C1A N1A 3.3(13) . . . . ?
C3A C2A C10A O1A -3.3(14) . . . . ?
C3A C2A C10A O2A 177.1(9) . . . . ?
C1A N1A C8A C9A 1.4(11) . . . . ?
C1A N1A C8A C7A -177.7(7) . . . . ?
C1A N1A C11A C12A -153.0(8) . . . . ?
C1A N1A C11A C13A 81.2(10) . . . . ?
C1A C2A C10A O1A 176.9(8) . . . . ?
C1A C2A C10A O2A -2.8(14) . . . . ?
C8A N1A C1A C2A -4.5(13) . . . . ?
C8A N1A C11A C12A 32.8(10) . . . . ?
C8A N1A C11A C13A -93.0(9) . . . . ?
C8A C9A C3A O3A 176.0(8) . . . . ?
C8A C9A C3A C2A -3.6(12) . . . . ?
C7A O4A C12A C11A 57.0(11) . . . . ?
C7A C6A C5A F1A -179.4(7) . . . . ?
C7A C6A C5A C4A -0.4(13) . . . . ?
C12A O4A C7A C6A 154.3(8) . . . . ?
C12A O4A C7A C8A -26.3(11) . . . . ?
C11A N1A C1A C2A -178.6(8) . . . . ?
C11A N1A C8A C9A 175.7(7) . . . . ?
C11A N1A C8A C7A -3.4(11) . . . . ?
C10A C2A C1A N1A -176.8(8) . . . . ?
F1C C5C C4C C9C -178.9(8) . . . . ?
O4C C12C C11C N1C -58.2(10) . . . . ?
O4C C12C C11C C13C 64.3(10) . . . . ?
O3C C3C C2C C1C -180.0(8) . . . . ?
O3C C3C C2C C10C -3.3(12) . . . . ?
N3C C16C C17C N2C -54.8(11) . . . . ?
N2C C14C C15C N3C 52.9(11) . . . . ?
N2C C6C C5C F1C -4.4(13) . . . . ?
N2C C6C C5C C4C 178.1(9) . . . . ?
N2C C6C C7C O4C 1.2(14) . . . . ?
N2C C6C C7C C8C -176.7(8) . . . . ?
N1C C8C C7C O4C -1.5(12) . . . . ?
N1C C8C C7C C6C 176.4(8) . . . . ?
C18C N3C C16C C17C -176.0(11) . . . . ?
C18C N3C C15C C14C -179.7(10) . . . . ?
C16C N3C C15C C14C -55.9(11) . . . . ?
C17C N2C C14C C15C -53.5(11) . . . . ?
C17C N2C C6C C5C -44.7(14) . . . . ?
C17C N2C C6C C7C 133.9(10) . . . . ?
C14C N2C C17C C16C 53.8(11) . . . . ?
C14C N2C C6C C5C 140.5(10) . . . . ?
C14C N2C C6C C7C -40.9(15) . . . . ?
C15C N3C C16C C17C 56.8(11) . . . . ?
C6C N2C C17C C16C -121.5(9) . . . . ?
C6C N2C C14C C15C 121.7(10) . . . . ?
C6C C5C C4C C9C -1.5(14) . . . . ?
C5C C6C C7C O4C 179.9(8) . . . . ?
C5C C6C C7C C8C 1.9(13) . . . . ?
C5C C4C C9C C3C -179.2(8) . . . . ?
C5C C4C C9C C8C 2.2(12) . . . . ?
C4C C9C C3C O3C 0.6(13) . . . . ?
C4C C9C C3C C2C 177.5(7) . . . . ?
C4C C9C C8C N1C -178.6(7) . . . . ?
C4C C9C C8C C7C -0.9(12) . . . . ?
C9C C3C C2C C1C 3.1(11) . . . . ?
C9C C3C C2C C10C 179.8(7) . . . . ?
C9C C8C C7C O4C -179.2(7) . . . . ?
C9C C8C C7C C6C -1.2(13) . . . . ?
C3C C9C C8C N1C 2.8(12) . . . . ?
C3C C9C C8C C7C -179.5(7) . . . . ?
C3C C2C C1C N1C -1.2(14) . . . . ?
C3C C2C C10C O1C -0.3(11) . . . . ?
C3C C2C C10C O2C -178.8(8) . . . . ?
C1C N1C C8C C9C -0.7(11) . . . . ?
C1C N1C C8C C7C -178.4(7) . . . . ?
C1C N1C C11C C12C -153.3(8) . . . . ?
C1C N1C C11C C13C 84.2(10) . . . . ?
C1C C2C C10C O1C 176.3(8) . . . . ?
C1C C2C C10C O2C -2.2(14) . . . . ?
C8C N1C C1C C2C -0.1(13) . . . . ?
C8C N1C C11C C12C 31.9(10) . . . . ?
C8C N1C C11C C13C -90.6(9) . . . . ?
C8C C9C C3C O3C 179.2(7) . . . . ?
C8C C9C C3C C2C -3.9(11) . . . . ?
C7C O4C C12C C11C 57.0(10) . . . . ?
C7C C6C C5C F1C 176.9(8) . . . . ?
C7C C6C C5C C4C -0.6(14) . . . . ?
C12C O4C C7C C6C 155.0(8) . . . . ?
C12C O4C C7C C8C -27.0(11) . . . . ?
C11C N1C C1C C2C -174.8(8) . . . . ?
C11C N1C C8C C9C 174.2(7) . . . . ?
C11C N1C C8C C7C -3.5(11) . . . . ?
C10C C2C C1C N1C -177.9(8) . . . . ?
F1B C5B C4B C9B 179.1(8) . . . . ?
O4B C12B C11B N1B -55.9(11) . . . . ?
O4B C12B C11B C13B 68.3(11) . . . . ?
O3B C3B C2B C1B 176.1(8) . . . . ?
O3B C3B C2B C10B -0.6(13) . . . . ?
N3B C16B C17B N2B -55.3(12) . . . . ?
N2B C14B C15B N3B 57.9(13) . . . . ?
N2B C6B C5B F1B -3.8(14) . . . . ?
N2B C6B C5B C4B 178.1(9) . . . . ?
N2B C6B C7B O4B 1.5(13) . . . . ?
N2B C6B C7B C8B -176.8(8) . . . . ?
N1B C8B C7B O4B -2.5(13) . . . . ?
N1B C8B C7B C6B 175.6(7) . . . . ?
C18B N3B C16B C17B -179.8(11) . . . . ?
C18B N3B C15B C14B 179.9(11) . . . . ?
C16B N3B C15B C14B -58.7(13) . . . . ?
C17B N2B C14B C15B -56.4(12) . . . . ?
C17B N2B C6B C5B -43.6(14) . . . . ?
C17B N2B C6B C7B 133.9(10) . . . . ?
C14B N2B C17B C16B 52.6(12) . . . . ?
C14B N2B C6B C5B 136.0(10) . . . . ?
C14B N2B C6B C7B -46.4(14) . . . . ?
C15B N3B C16B C17B 58.2(13) . . . . ?
C6B N2B C17B C16B -127.7(10) . . . . ?
C6B N2B C14B C15B 123.9(11) . . . . ?
C6B C5B C4B C9B -2.9(14) . . . . ?
C5B C6B C7B O4B 179.2(8) . . . . ?
C5B C6B C7B C8B 0.9(13) . . . . ?
C5B C4B C9B C3B -179.2(8) . . . . ?
C5B C4B C9B C8B 3.8(12) . . . . ?
C4B C9B C3B O3B 3.1(13) . . . . ?
C4B C9B C3B C2B -179.4(8) . . . . ?
C4B C9B C8B N1B -177.9(7) . . . . ?
C4B C9B C8B C7B -2.6(12) . . . . ?
C9B C3B C2B C1B -1.3(12) . . . . ?
C9B C3B C2B C10B -178.0(7) . . . . ?
C9B C8B C7B O4B -177.9(7) . . . . ?
C9B C8B C7B C6B 0.2(13) . . . . ?
C3B C9B C8B N1B 5.1(11) . . . . ?
C3B C9B C8B C7B -179.6(7) . . . . ?
C3B C2B C1B N1B 2.6(13) . . . . ?
C3B C2B C10B O1B -3.6(12) . . . . ?
C3B C2B C10B O2B -179.2(9) . . . . ?
C1B N1B C8B C9B -3.8(11) . . . . ?
C1B N1B C8B C7B -179.3(7) . . . . ?
C1B N1B C11B C12B -151.6(8) . . . . ?
C1B N1B C11B C13B 84.3(10) . . . . ?
C1B C2B C10B O1B 179.5(8) . . . . ?
C1B C2B C10B O2B 4.0(14) . . . . ?
C8B N1B C1B C2B 0.0(12) . . . . ?
C8B N1B C11B C12B 29.8(11) . . . . ?
C8B N1B C11B C13B -94.2(10) . . . . ?
C8B C9B C3B O3B -180.0(8) . . . . ?
C8B C9B C3B C2B -2.5(11) . . . . ?
C7B O4B C12B C11B 53.1(10) . . . . ?
C7B C6B C5B F1B 178.5(7) . . . . ?
C7B C6B C5B C4B 0.4(14) . . . . ?
C12B O4B C7B C6B 157.9(8) . . . . ?
C12B O4B C7B C8B -24.0(11) . . . . ?
C11B N1B C1B C2B -178.6(8) . . . . ?
C11B N1B C8B C9B 174.8(8) . . . . ?
C11B N1B C8B C7B -0.7(11) . . . . ?
C10B C2B C1B N1B 179.5(8) . . . . ?
F1D C5D C4D C9D 176.5(8) . . . . ?
O4D C12D C11D N1D -63.8(10) . . . . ?
O4D C12D C11D C13D 60.7(10) . . . . ?
O3D C3D C2D C1D -179.3(8) . . . . ?
O3D C3D C2D C10D -2.6(14) . . . . ?
N3D C16D C17D N2D 58.4(11) . . . . ?
N2D C14D C15D N3D -58.2(12) . . . . ?
N2D C6D C5D F1D 0.8(14) . . . . ?
N2D C6D C5D C4D -177.5(9) . . . . ?
N2D C6D C7D O4D 2.8(13) . . . . ?
N2D C6D C7D C8D -177.2(8) . . . . ?
N1D C8D C7D O4D 0.4(14) . . . . ?
N1D C8D C7D C6D -179.6(8) . . . . ?
C18D N3D C16D C17D 177.4(9) . . . . ?
C18D N3D C15D C14D -179.0(9) . . . . ?
C16D N3D C15D C14D 60.5(11) . . . . ?
C17D N2D C14D C15D 57.0(12) . . . . ?
C17D N2D C6D C5D 31.6(14) . . . . ?
C17D N2D C6D C7D -149.4(10) . . . . ?
C14D N2D C17D C16D -57.1(12) . . . . ?
C14D N2D C6D C5D -112.6(12) . . . . ?
C14D N2D C6D C7D 66.4(12) . . . . ?
C15D N3D C16D C17D -62.7(11) . . . . ?
C6D N2D C17D C16D 156.3(9) . . . . ?
C6D N2D C14D C15D -156.2(9) . . . . ?
C6D C5D C4D C9D -5.2(14) . . . . ?
C5D C6D C7D O4D -178.1(8) . . . . ?
C5D C6D C7D C8D 1.9(13) . . . . ?
C5D C4D C9D C3D 179.4(8) . . . . ?
C5D C4D C9D C8D 1.5(13) . . . . ?
C4D C9D C3D O3D 1.4(13) . . . . ?
C4D C9D C3D C2D 177.8(8) . . . . ?
C4D C9D C8D N1D 177.8(8) . . . . ?
C4D C9D C8D C7D 3.6(13) . . . . ?
C9D C3D C2D C1D 4.5(13) . . . . ?
C9D C3D C2D C10D -178.8(7) . . . . ?
C9D C8D C7D O4D 174.7(8) . . . . ?
C9D C8D C7D C6D -5.3(14) . . . . ?
C3D C9D C8D N1D -0.2(12) . . . . ?
C3D C9D C8D C7D -174.4(8) . . . . ?
C3D C2D C1D N1D 0.4(14) . . . . ?
C3D C2D C10D O1D -1.3(12) . . . . ?
C3D C2D C10D O2D -178.8(8) . . . . ?
C1D N1D C8D C9D 5.0(12) . . . . ?
C1D N1D C8D C7D 179.4(8) . . . . ?
C1D N1D C11D C12D -149.0(9) . . . . ?
C1D N1D C11D C13D 84.5(11) . . . . ?
C1D C2D C10D O1D 175.6(8) . . . . ?
C1D C2D C10D O2D -2.0(13) . . . . ?
C8D N1D C1D C2D -5.3(13) . . . . ?
C8D N1D C11D C12D 39.5(11) . . . . ?
C8D N1D C11D C13D -87.0(9) . . . . ?
C8D C9D C3D O3D 179.3(8) . . . . ?
C8D C9D C3D C2D -4.4(12) . . . . ?
C7D O4D C12D C11D 57.9(10) . . . . ?
C7D C6D C5D F1D -178.2(8) . . . . ?
C7D C6D C5D C4D 3.4(14) . . . . ?
C12D O4D C7D C6D 154.1(8) . . . . ?
C12D O4D C7D C8D -25.9(12) . . . . ?
C11D N1D C1D C2D -176.6(8) . . . . ?
C11D N1D C8D C9D 176.8(8) . . . . ?
C11D N1D C8D C7D -8.8(12) . . . . ?
C10D C2D C1D N1D -176.5(8) . . . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.237 -0.112 0.000 1575 710 ' '
2 0.500 0.179 0.500 138 48 ' '
3 0.000 0.679 0.500 138 48 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
