# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1470803'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-06-26 downloaded from the CCDC.
;
_audit_creation_date             2015-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H17 F3 N2 O5, C3 H7 N O, C2 H6 O'
_chemical_formula_sum            'C34 H30 F3 N3 O7'
_chemical_formula_weight         649.61
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4101(6)
_cell_length_b                   12.6325(6)
_cell_length_c                   13.2754(6)
_cell_angle_alpha                91.976(4)
_cell_angle_beta                 92.533(4)
_cell_angle_gamma                113.252(5)
_cell_volume                     1599.86(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3331
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2450
_cell_measurement_theta_min      3.3150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11560
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.074
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4631
_reflns_number_total             6825
_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, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6825
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0739
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0756P)²+0.7739P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1921
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C1-O1AA = C1-C2AB
 1.5 with sigma of 0.02
 C2-C1
 1.5 with sigma of 0.02
 C2-C1
 1.5 with sigma of 0.02
 C2-C1
 1.5 with sigma of 0.02
 C2-C1
 1.5 with sigma of 0.02
 C2-C1
 1.5 with sigma of 0.02
 C2-C1
 1.5 with sigma of 0.02
 C2AB-C1
 1.5 with sigma of 0.02
 C2-C1 = C2AB-C1
 1.5 with sigma of 0.02
 C2AB-C1 = C2-C1
 1.5 with sigma of 0.02
 C2AB-C1
 1.53 with sigma of 0.02
 C2AB-C1
 1.53 with sigma of 0.02
 C2-C1
 1.53 with sigma of 0.02
 C2AB-C1 \\sim C1-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
: with sigma of 0.1 and sigma for terminal atoms of 0.2
: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Sof(H1BD)=Sof(H1BE)=Sof(C2AB)=Sof(H2AB)=Sof(H2AC)=Sof(H2AD)=1-FVAR(1)
 Sof(H1AC)=Sof(H1AB)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AC,H1AB), C1(H1BD,H1BE)
5.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AB), C26(H26), C22(H22), C32(H32), C25(H25), C5(H5A), C28(H28),
 C2AA(H2AA), C14(H14), C29(H29), C23(H23), C20(H20), C13(H13), C19(H19),
 C16(H16)
5.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C2AB(H2AB,H2AC,H2AD), C2(H2A,H2B,H2C)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O0AA(H0AA), O1AA(H1AA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
F2 F 0.9373(2) 0.39728(19) 0.15222(17) 0.0914(7) Uani 1 1 d . . . . .
F1 F 0.0131(3) -0.3827(2) 0.37068(18) 0.1050(8) Uani 1 1 d . . . . .
F3 F -0.2442(2) -0.2424(2) -0.20822(18) 0.1060(9) Uani 1 1 d . . . . .
O5 O 0.4483(3) 0.2920(2) -0.07388(19) 0.0780(8) Uani 1 1 d . . . . .
O3 O 0.5882(3) 0.2475(2) 0.57740(15) 0.0650(6) Uani 1 1 d . . . . .
H3 H 0.5816 0.2975 0.6153 0.098 Uiso 1 1 calc GR . . . .
O6 O 0.9064(3) -0.1531(2) 0.54392(18) 0.0687(6) Uani 1 1 d . . . . .
O0AA O 0.7604(3) -0.0395(2) 0.48383(15) 0.0636(6) Uani 1 1 d . . . . .
H0AA H 0.8105 -0.0752 0.4927 0.095 Uiso 1 1 calc GR . . . .
O1 O 0.7406(3) -0.1103(2) 0.32569(17) 0.0723(7) Uani 1 1 d . . . . .
O4 O 0.4974(2) 0.3269(2) 0.46207(16) 0.0621(6) Uani 1 1 d . . . . .
N3 N 0.8856(3) -0.3322(3) 0.5787(3) 0.0732(8) Uani 1 1 d . . . . .
N2 N 0.3528(2) 0.0888(2) -0.00463(16) 0.0456(6) Uani 1 1 d . . . . .
N1 N 0.4262(2) 0.06155(19) 0.14690(15) 0.0410(5) Uani 1 1 d . . . . .
C30 C 1.0305(4) -0.2976(4) 0.6122(3) 0.0875(12) Uani 1 1 d . . . . .
H30A H 1.0370 -0.3130 0.6822 0.131 Uiso 1 1 calc GR . . . .
H30B H 1.0799 -0.2165 0.6040 0.131 Uiso 1 1 calc GR . . . .
H30C H 1.0711 -0.3402 0.5728 0.131 Uiso 1 1 calc GR . . . .
C0AA C 0.8008(4) 0.4506(3) 0.0350(3) 0.0651(9) Uani 1 1 d . . . . .
H0AB H 0.8750 0.5212 0.0291 0.078 Uiso 1 1 calc R . . . .
C26 C -0.1172(3) -0.2161(3) -0.0523(3) 0.0651(9) Uani 1 1 d . . . . .
H26 H -0.1939 -0.2733 -0.0262 0.078 Uiso 1 1 calc R . . . .
C22 C 0.0984(4) -0.1870(3) 0.3396(2) 0.0671(9) Uani 1 1 d . . . . .
H22 H 0.0587 -0.1730 0.3973 0.081 Uiso 1 1 calc R . . . .
C6 C 0.8124(3) 0.3719(3) 0.0993(2) 0.0606(8) Uani 1 1 d . . . . .
C32 C 0.8382(4) -0.2562(4) 0.5472(3) 0.0689(9) Uani 1 1 d . . . . .
H32 H 0.7439 -0.2837 0.5255 0.083 Uiso 1 1 calc R . . . .
C25 C 0.0051(3) -0.1585(3) 0.0067(2) 0.0564(8) Uani 1 1 d . . . . .
H25 H 0.0100 -0.1766 0.0737 0.068 Uiso 1 1 calc R . . . .
C21 C 0.0865(4) -0.2948(3) 0.3124(2) 0.0636(9) Uani 1 1 d . . . . .
C4 C 0.5773(3) 0.2393(2) 0.05761(19) 0.0448(6) Uani 1 1 d . . . . .
C3 C 0.5649(3) 0.3164(3) -0.0124(2) 0.0537(8) Uani 1 1 d . . . . .
C12 C 0.6375(3) 0.0221(2) 0.36420(19) 0.0412(6) Uani 1 1 d . . . . .
C17 C 0.5450(3) 0.2576(3) 0.4847(2) 0.0453(7) Uani 1 1 d . . . . .
C5 C 0.7053(3) 0.2683(3) 0.1122(2) 0.0522(7) Uani 1 1 d . . . . .
H5A H 0.7176 0.2176 0.1569 0.063 Uiso 1 1 calc R . . . .
C15 C 0.7179(3) -0.0500(3) 0.3881(2) 0.0479(7) Uani 1 1 d . . . . .
C28 C -0.0127(4) -0.1040(3) -0.1912(2) 0.0666(9) Uani 1 1 d . . . . .
H28 H -0.0196 -0.0859 -0.2579 0.080 Uiso 1 1 calc R . . . .
C2AA C 0.6760(4) 0.4217(3) -0.0206(3) 0.0653(9) Uani 1 1 d . . . . .
H2AA H 0.6658 0.4739 -0.0646 0.078 Uiso 1 1 calc R . . . .
C27 C -0.1222(4) -0.1868(3) -0.1504(3) 0.0682(10) Uani 1 1 d . . . . .
C14 C 0.6279(3) 0.1014(2) 0.43497(19) 0.0414(6) Uani 1 1 d . . . . .
H14 H 0.6685 0.1077 0.4999 0.050 Uiso 1 1 calc R . . . .
C11 C 0.5586(3) 0.1715(2) 0.40994(18) 0.0394(6) Uani 1 1 d . . . . .
C29 C 0.1091(3) -0.0473(3) -0.1316(2) 0.0539(8) Uani 1 1 d . . . . .
H29 H 0.1847 0.0099 -0.1587 0.065 Uiso 1 1 calc R . . . .
C24 C 0.1211(3) -0.0741(2) -0.0317(2) 0.0445(6) Uani 1 1 d . . . . .
C23 C 0.1716(3) -0.0977(3) 0.2793(2) 0.0538(7) Uani 1 1 d . . . . .
H23 H 0.1814 -0.0228 0.2967 0.065 Uiso 1 1 calc R . . . .
C20 C 0.1441(4) -0.3201(3) 0.2301(3) 0.0642(9) Uani 1 1 d . . . . .
H20 H 0.1350 -0.3951 0.2143 0.077 Uiso 1 1 calc R . . . .
C8 C 0.2525(3) -0.0101(2) 0.02964(19) 0.0419(6) Uani 1 1 d . . . . .
C13 C 0.5722(3) 0.0099(2) 0.26794(19) 0.0421(6) Uani 1 1 d . . . . .
H13 H 0.5762 -0.0443 0.2203 0.050 Uiso 1 1 calc R . . . .
C19 C 0.2168(3) -0.2310(3) 0.1706(2) 0.0549(8) Uani 1 1 d . . . . .
H19 H 0.2576 -0.2462 0.1140 0.066 Uiso 1 1 calc R . . . .
C16 C 0.4944(3) 0.1601(2) 0.31371(19) 0.0411(6) Uani 1 1 d . . . . .
H16 H 0.4473 0.2067 0.2965 0.049 Uiso 1 1 calc R . . . .
C10 C 0.5013(3) 0.0790(2) 0.24399(18) 0.0393(6) Uani 1 1 d . . . . .
C31 C 0.7950(6) -0.4539(4) 0.5779(7) 0.181(3) Uani 1 1 d . . . . .
H31A H 0.7691 -0.4743 0.6453 0.271 Uiso 1 1 calc GR . . . .
H31B H 0.8438 -0.4989 0.5528 0.271 Uiso 1 1 calc GR . . . .
H31C H 0.7123 -0.4691 0.5350 0.271 Uiso 1 1 calc GR . . . .
C18 C 0.2298(3) -0.1198(2) 0.19356(18) 0.0407(6) Uani 1 1 d . . . . .
C7 C 0.4555(3) 0.1306(2) 0.06654(19) 0.0422(6) Uani 1 1 d . . . . .
C9 C 0.2967(3) -0.0283(2) 0.12364(18) 0.0411(6) Uani 1 1 d . . . . .
O1AA O 0.5229(4) -0.6269(2) 0.71569(18) 0.0976(10) Uani 1 1 d D . . . .
H1AA H 0.5155 -0.6570 0.7701 0.146 Uiso 1 1 calc GR . . . .
C1 C 0.4209(9) -0.5748(7) 0.7045(6) 0.182(3) Uani 1 1 d D . . . .
H1AC H 0.4179 -0.5551 0.6348 0.218 Uiso 0.484(12) 1 calc R . P A 1
H1AB H 0.3297 -0.6337 0.7159 0.218 Uiso 0.484(12) 1 calc R . P A 1
H1BD H 0.3907 -0.5899 0.6334 0.218 Uiso 0.516(12) 1 calc R . P A 2
H1BE H 0.4783 -0.4928 0.7121 0.218 Uiso 0.516(12) 1 calc R . P A 2
C2AB C 0.2928(16) -0.5854(17) 0.7530(14) 0.219(10) Uiso 0.516(12) 1 d D U P A 2
H2AB H 0.2229 -0.6622 0.7398 0.328 Uiso 0.516(12) 1 calc GR . P A 2
H2AC H 0.2588 -0.5310 0.7264 0.328 Uiso 0.516(12) 1 calc GR . P A 2
H2AD H 0.3130 -0.5699 0.8246 0.328 Uiso 0.516(12) 1 calc GR . P A 2
C2 C 0.4395(12) -0.4729(9) 0.7680(8) 0.112(5) Uiso 0.484(12) 1 d D . P A 1
H2A H 0.4184 -0.4945 0.8359 0.168 Uiso 0.484(12) 1 calc GR . P A 1
H2B H 0.3775 -0.4390 0.7425 0.168 Uiso 0.484(12) 1 calc GR . P A 1
H2C H 0.5346 -0.4179 0.7674 0.168 Uiso 0.484(12) 1 calc GR . P A 1
H5 H 0.384(5) 0.209(5) -0.066(4) 0.130(18) Uiso 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
F2 C6 1.363(4) . ?
F1 C21 1.363(3) . ?
F3 C27 1.367(4) . ?
O5 C3 1.354(4) . ?
O5 H5 1.01(5) . ?
O3 H3 0.8200 . ?
O3 C17 1.320(3) . ?
O6 C32 1.216(4) . ?
O0AA H0AA 0.8200 . ?
O0AA C15 1.312(3) . ?
O1 C15 1.200(4) . ?
O4 C17 1.205(3) . ?
N3 C30 1.439(5) . ?
N3 C32 1.312(5) . ?
N3 C31 1.451(5) . ?
N2 C8 1.382(3) . ?
N2 C7 1.321(3) . ?
N1 C10 1.441(3) . ?
N1 C7 1.369(3) . ?
N1 C9 1.390(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C0AA H0AB 0.9300 . ?
C0AA C6 1.370(5) . ?
C0AA C2AA 1.374(5) . ?
C26 H26 0.9300 . ?
C26 C25 1.380(4) . ?
C26 C27 1.371(5) . ?
C22 H22 0.9300 . ?
C22 C21 1.352(5) . ?
C22 C23 1.390(4) . ?
C6 C5 1.365(4) . ?
C32 H32 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.390(4) . ?
C21 C20 1.356(5) . ?
C4 C3 1.408(4) . ?
C4 C5 1.395(4) . ?
C4 C7 1.468(4) . ?
C3 C2AA 1.387(4) . ?
C12 C15 1.493(4) . ?
C12 C14 1.385(4) . ?
C12 C13 1.395(4) . ?
C17 C11 1.499(4) . ?
C5 H5A 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.356(5) . ?
C28 C29 1.379(4) . ?
C2AA H2AA 0.9300 . ?
C14 H14 0.9300 . ?
C14 C11 1.385(4) . ?
C11 C16 1.391(3) . ?
C29 H29 0.9300 . ?
C29 C24 1.393(4) . ?
C24 C8 1.474(4) . ?
C23 H23 0.9300 . ?
C23 C18 1.384(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.380(4) . ?
C8 C9 1.369(4) . ?
C13 H13 0.9300 . ?
C13 C10 1.384(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C10 1.382(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C18 C9 1.476(4) . ?
O1AA H1AA 0.8200 . ?
O1AA C1 1.458(7) . ?
C1 H1AC 0.9700 . ?
C1 H1AB 0.9700 . ?
C1 H1BD 0.9700 . ?
C1 H1BE 0.9700 . ?
C1 C2AB 1.467(7) . ?
C1 C2 1.456(6) . ?
C2AB H2AB 0.9600 . ?
C2AB H2AC 0.9600 . ?
C2AB H2AD 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C3 O5 H5 108(3) . . ?
C17 O3 H3 109.5 . . ?
C15 O0AA H0AA 109.5 . . ?
C30 N3 C31 117.9(4) . . ?
C32 N3 C30 120.8(3) . . ?
C32 N3 C31 121.2(4) . . ?
C7 N2 C8 107.4(2) . . ?
C7 N1 C10 129.3(2) . . ?
C7 N1 C9 107.2(2) . . ?
C9 N1 C10 123.1(2) . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
N3 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C6 C0AA H0AB 121.1 . . ?
C6 C0AA C2AA 117.8(3) . . ?
C2AA C0AA H0AB 121.1 . . ?
C25 C26 H26 121.0 . . ?
C27 C26 H26 121.0 . . ?
C27 C26 C25 118.1(3) . . ?
C21 C22 H22 120.8 . . ?
C21 C22 C23 118.3(3) . . ?
C23 C22 H22 120.8 . . ?
F2 C6 C0AA 118.6(3) . . ?
F2 C6 C5 118.3(3) . . ?
C5 C6 C0AA 123.1(3) . . ?
O6 C32 N3 125.8(3) . . ?
O6 C32 H32 117.1 . . ?
N3 C32 H32 117.1 . . ?
C26 C25 H25 119.2 . . ?
C26 C25 C24 121.5(3) . . ?
C24 C25 H25 119.2 . . ?
C22 C21 F1 118.4(3) . . ?
C22 C21 C20 123.5(3) . . ?
C20 C21 F1 118.2(3) . . ?
C3 C4 C7 117.9(3) . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 C7 123.7(3) . . ?
O5 C3 C4 122.6(3) . . ?
O5 C3 C2AA 117.8(3) . . ?
C2AA C3 C4 119.6(3) . . ?
C14 C12 C15 121.5(2) . . ?
C14 C12 C13 119.5(3) . . ?
C13 C12 C15 119.0(3) . . ?
O3 C17 C11 112.8(3) . . ?
O4 C17 O3 124.0(3) . . ?
O4 C17 C11 123.2(2) . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
O0AA C15 C12 112.6(3) . . ?
O1 C15 O0AA 124.4(3) . . ?
O1 C15 C12 123.0(3) . . ?
C27 C28 H28 120.7 . . ?
C27 C28 C29 118.6(3) . . ?
C29 C28 H28 120.7 . . ?
C0AA C2AA C3 121.5(3) . . ?
C0AA C2AA H2AA 119.3 . . ?
C3 C2AA H2AA 119.3 . . ?
F3 C27 C26 118.1(3) . . ?
C28 C27 F3 119.2(3) . . ?
C28 C27 C26 122.8(3) . . ?
C12 C14 H14 119.7 . . ?
C11 C14 C12 120.7(2) . . ?
C11 C14 H14 119.7 . . ?
C14 C11 C17 122.2(2) . . ?
C14 C11 C16 119.9(3) . . ?
C16 C11 C17 117.9(2) . . ?
C28 C29 H29 119.4 . . ?
C28 C29 C24 121.3(3) . . ?
C24 C29 H29 119.4 . . ?
C25 C24 C29 117.7(3) . . ?
C25 C24 C8 122.8(2) . . ?
C29 C24 C8 119.4(3) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 C22 120.3(3) . . ?
C18 C23 H23 119.9 . . ?
C21 C20 H20 121.1 . . ?
C21 C20 C19 117.9(3) . . ?
C19 C20 H20 121.1 . . ?
N2 C8 C24 120.3(2) . . ?
C9 C8 N2 108.9(2) . . ?
C9 C8 C24 130.7(2) . . ?
C12 C13 H13 120.3 . . ?
C10 C13 C12 119.4(3) . . ?
C10 C13 H13 120.3 . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 H19 119.4 . . ?
C11 C16 H16 120.3 . . ?
C10 C16 C11 119.3(3) . . ?
C10 C16 H16 120.3 . . ?
C13 C10 N1 119.5(2) . . ?
C16 C10 N1 119.2(2) . . ?
C16 C10 C13 121.2(2) . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C23 C18 C9 121.0(3) . . ?
C19 C18 C23 118.9(3) . . ?
C19 C18 C9 120.0(2) . . ?
N2 C7 N1 110.2(2) . . ?
N2 C7 C4 122.2(2) . . ?
N1 C7 C4 127.5(2) . . ?
N1 C9 C18 122.7(2) . . ?
C8 C9 N1 106.3(2) . . ?
C8 C9 C18 131.1(2) . . ?
C1 O1AA H1AA 109.5 . . ?
O1AA C1 H1AC 107.5 . . ?
O1AA C1 H1AB 107.5 . . ?
O1AA C1 H1BD 103.3 . . ?
O1AA C1 H1BE 103.3 . . ?
O1AA C1 C2AB 135.7(11) . . ?
H1AC C1 H1AB 107.0 . . ?
H1BD C1 H1BE 105.2 . . ?
C2AB C1 H1BD 103.3 . . ?
C2AB C1 H1BE 103.3 . . ?
C2 C1 O1AA 119.2(7) . . ?
C2 C1 H1AC 107.5 . . ?
C2 C1 H1AB 107.5 . . ?
C1 C2AB H2AB 109.5 . . ?
C1 C2AB H2AC 109.5 . . ?
C1 C2AB H2AD 109.5 . . ?
H2AB C2AB H2AC 109.5 . . ?
H2AB C2AB H2AD 109.5 . . ?
H2AC C2AB H2AD 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
F2 C6 C5 C4 -178.9(3) . . . . ?
F1 C21 C20 C19 179.2(3) . . . . ?
O5 C3 C2AA C0AA -176.4(3) . . . . ?
O3 C17 C11 C14 -8.7(4) . . . . ?
O3 C17 C11 C16 169.0(2) . . . . ?
O4 C17 C11 C14 172.5(3) . . . . ?
O4 C17 C11 C16 -9.8(4) . . . . ?
N2 C8 C9 N1 0.1(3) . . . . ?
N2 C8 C9 C18 179.4(3) . . . . ?
C30 N3 C32 O6 -0.9(6) . . . . ?
C0AA C6 C5 C4 0.3(5) . . . . ?
C26 C25 C24 C29 1.4(5) . . . . ?
C26 C25 C24 C8 179.2(3) . . . . ?
C22 C21 C20 C19 -1.1(6) . . . . ?
C22 C23 C18 C19 -1.5(4) . . . . ?
C22 C23 C18 C9 174.4(3) . . . . ?
C6 C0AA C2AA C3 -0.1(5) . . . . ?
C25 C26 C27 F3 -178.8(3) . . . . ?
C25 C26 C27 C28 0.0(6) . . . . ?
C25 C24 C8 N2 -165.9(3) . . . . ?
C25 C24 C8 C9 11.1(5) . . . . ?
C21 C22 C23 C18 0.2(5) . . . . ?
C21 C20 C19 C18 -0.4(5) . . . . ?
C4 C3 C2AA C0AA 3.0(5) . . . . ?
C3 C4 C5 C6 2.6(5) . . . . ?
C3 C4 C7 N2 19.0(4) . . . . ?
C3 C4 C7 N1 -157.8(3) . . . . ?
C12 C14 C11 C17 179.5(2) . . . . ?
C12 C14 C11 C16 1.8(4) . . . . ?
C12 C13 C10 N1 -176.0(2) . . . . ?
C12 C13 C10 C16 0.1(4) . . . . ?
C17 C11 C16 C10 -178.0(2) . . . . ?
C5 C4 C3 O5 175.1(3) . . . . ?
C5 C4 C3 C2AA -4.2(5) . . . . ?
C5 C4 C7 N2 -158.9(3) . . . . ?
C5 C4 C7 N1 24.4(5) . . . . ?
C15 C12 C14 C11 176.9(2) . . . . ?
C15 C12 C13 C10 -177.9(2) . . . . ?
C28 C29 C24 C25 -1.2(5) . . . . ?
C28 C29 C24 C8 -179.1(3) . . . . ?
C2AA C0AA C6 F2 177.6(3) . . . . ?
C2AA C0AA C6 C5 -1.6(6) . . . . ?
C27 C26 C25 C24 -0.9(5) . . . . ?
C27 C28 C29 C24 0.4(5) . . . . ?
C14 C12 C15 O0AA 8.0(4) . . . . ?
C14 C12 C15 O1 -171.9(3) . . . . ?
C14 C12 C13 C10 1.4(4) . . . . ?
C14 C11 C16 C10 -0.3(4) . . . . ?
C11 C16 C10 N1 175.5(2) . . . . ?
C11 C16 C10 C13 -0.7(4) . . . . ?
C29 C28 C27 F3 179.1(3) . . . . ?
C29 C28 C27 C26 0.3(6) . . . . ?
C29 C24 C8 N2 11.8(4) . . . . ?
C29 C24 C8 C9 -171.2(3) . . . . ?
C24 C8 C9 N1 -177.1(3) . . . . ?
C24 C8 C9 C18 2.2(5) . . . . ?
C23 C22 C21 F1 -179.1(3) . . . . ?
C23 C22 C21 C20 1.1(6) . . . . ?
C23 C18 C9 N1 73.2(4) . . . . ?
C23 C18 C9 C8 -106.0(4) . . . . ?
C20 C19 C18 C23 1.6(5) . . . . ?
C20 C19 C18 C9 -174.4(3) . . . . ?
C8 N2 C7 N1 0.3(3) . . . . ?
C8 N2 C7 C4 -176.9(3) . . . . ?
C13 C12 C15 O0AA -172.8(2) . . . . ?
C13 C12 C15 O1 7.4(4) . . . . ?
C13 C12 C14 C11 -2.4(4) . . . . ?
C19 C18 C9 N1 -110.9(3) . . . . ?
C19 C18 C9 C8 69.9(4) . . . . ?
C10 N1 C7 N2 -173.7(3) . . . . ?
C10 N1 C7 C4 3.3(5) . . . . ?
C10 N1 C9 C8 174.0(2) . . . . ?
C10 N1 C9 C18 -5.3(4) . . . . ?
C31 N3 C32 O6 -179.0(5) . . . . ?
C7 N2 C8 C24 177.3(3) . . . . ?
C7 N2 C8 C9 -0.3(3) . . . . ?
C7 N1 C10 C13 -110.4(3) . . . . ?
C7 N1 C10 C16 73.4(4) . . . . ?
C7 N1 C9 C8 0.0(3) . . . . ?
C7 N1 C9 C18 -179.3(3) . . . . ?
C7 C4 C3 O5 -2.9(5) . . . . ?
C7 C4 C3 C2AA 177.8(3) . . . . ?
C7 C4 C5 C6 -179.5(3) . . . . ?
C9 N1 C10 C13 77.0(3) . . . . ?
C9 N1 C10 C16 -99.2(3) . . . . ?
C9 N1 C7 N2 -0.2(3) . . . . ?
C9 N1 C7 C4 176.8(3) . . . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1470804'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-06-26 downloaded from the CCDC.
;
_audit_creation_date             2015-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H17 F3 N2 O5, C H4 O'
_chemical_formula_sum            'C30 H22 F3 N2 O6'
_chemical_formula_weight         563.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4844(5)
_cell_length_b                   11.9760(6)
_cell_length_c                   12.6807(6)
_cell_angle_alpha                70.466(4)
_cell_angle_beta                 70.427(4)
_cell_angle_gamma                75.767(4)
_cell_volume                     1264.39(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3753
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6840
_cell_measurement_theta_min      3.4400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             582
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.794
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9460
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.126
_diffrn_reflns_theta_min         3.275
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.794
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3682
_reflns_number_total             5395
_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, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0565P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1212
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C23(H23), C27(H27), C5(H5A), C15(H15), C21(H21), C12(H12), C1(H1A),
 C2(H2A), C11(H11), C14(H14), C17(H17), C18(H18), C20(H20)
2.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5), O2(H2), O1(H1), O6(H6)
;
_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
O5 O 0.63511(15) 0.41820(13) 0.38540(10) 0.0287(3) Uani 1 1 d . . . . .
H5 H 0.7209 0.4337 0.3496 0.043 Uiso 1 1 calc GR . . . .
O3 O 0.09720(15) 0.39157(13) 0.44511(11) 0.0305(3) Uani 1 1 d . . . . .
F1 F 0.34426(16) -0.13540(11) 0.58978(10) 0.0446(4) Uani 1 1 d . . . . .
O2 O -0.03487(15) 0.30085(14) 0.62457(11) 0.0335(4) Uani 1 1 d . . . . .
H2 H -0.1028 0.3167 0.5930 0.050 Uiso 1 1 calc GR . . . .
F2 F 0.18343(16) 0.09011(11) 1.51240(9) 0.0426(3) Uani 1 1 d . . . . .
O1 O 0.06501(16) -0.14852(13) 1.04619(11) 0.0309(3) Uani 1 1 d . . . . .
H1 H 0.1057 -0.1118 1.0692 0.046 Uiso 1 1 calc GR . . . .
O4 O 0.74201(16) 0.32590(14) 0.53031(12) 0.0376(4) Uani 1 1 d . . . . .
N8 N 0.25101(17) -0.00948(13) 1.03172(12) 0.0214(4) Uani 1 1 d . . . . .
N10 N 0.33374(17) 0.12159(14) 0.86286(12) 0.0204(3) Uani 1 1 d . . . . .
C25 C 0.3598(2) 0.34117(17) 0.52128(15) 0.0211(4) Uani 1 1 d . . . . .
H25 H 0.3654 0.3898 0.4459 0.025 Uiso 1 1 calc R . . . .
C10 C 0.2737(2) 0.08103(17) 1.17352(15) 0.0222(4) Uani 1 1 d . . . . .
C26 C 0.2238(2) 0.30199(16) 0.59327(15) 0.0205(4) Uani 1 1 d . . . . .
C23 C 0.4794(2) 0.23148(17) 0.67350(15) 0.0226(4) Uani 1 1 d . . . . .
H23 H 0.5656 0.2055 0.6998 0.027 Uiso 1 1 calc R . . . .
C4 C 0.2402(2) -0.05984(17) 0.86311(15) 0.0221(4) Uani 1 1 d . . . . .
C27 C 0.2149(2) 0.22974(17) 0.70617(15) 0.0216(4) Uani 1 1 d . . . . .
H27 H 0.1235 0.2054 0.7551 0.026 Uiso 1 1 calc R . . . .
C24 C 0.4868(2) 0.30748(17) 0.56237(15) 0.0209(4) Uani 1 1 d . . . . .
C22 C 0.3431(2) 0.19444(16) 0.74511(14) 0.0196(4) Uani 1 1 d . . . . .
F3 F 0.55104(18) 0.60098(12) 0.83024(12) 0.0602(4) Uani 1 1 d . . . . .
C7 C 0.2753(2) 0.01588(17) 0.91799(15) 0.0206(4) Uani 1 1 d . . . . .
C8 C 0.2943(2) 0.08124(17) 1.05295(15) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.3465(2) 0.16382(17) 0.94937(14) 0.0208(4) Uani 1 1 d . . . . .
C28 C 0.0905(2) 0.33673(17) 0.54594(15) 0.0230(4) Uani 1 1 d . . . . .
C3 C 0.1317(2) -0.13745(17) 0.93118(16) 0.0241(4) Uani 1 1 d . . . . .
C29 C 0.6336(2) 0.35037(18) 0.49187(15) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.3113(2) -0.06107(18) 0.74723(16) 0.0265(5) Uani 1 1 d . . . . .
H5A H 0.3861 -0.0135 0.7016 0.032 Uiso 1 1 calc R . . . .
C16 C 0.4012(2) 0.27870(17) 0.92001(14) 0.0218(4) Uani 1 1 d . . . . .
C15 C 0.1958(2) -0.00374(18) 1.26653(16) 0.0279(5) Uani 1 1 d . . . . .
H15 H 0.1622 -0.0620 1.2514 0.034 Uiso 1 1 calc R . . . .
C6 C 0.2700(2) -0.13277(19) 0.70153(17) 0.0305(5) Uani 1 1 d . . . . .
C21 C 0.3003(2) 0.38314(18) 0.92395(17) 0.0314(5) Uani 1 1 d . . . . .
H21 H 0.1970 0.3804 0.9464 0.038 Uiso 1 1 calc R . . . .
C12 C 0.2959(2) 0.16825(19) 1.31292(16) 0.0319(5) Uani 1 1 d . . . . .
H12 H 0.3294 0.2260 1.3289 0.038 Uiso 1 1 calc R . . . .
C1 C 0.1563(2) -0.20142(19) 0.76387(18) 0.0338(5) Uani 1 1 d . . . . .
H1A H 0.1260 -0.2453 0.7292 0.041 Uiso 1 1 calc R . . . .
C2 C 0.0887(2) -0.20347(19) 0.87872(17) 0.0306(5) Uani 1 1 d . . . . .
H2A H 0.0124 -0.2501 0.9222 0.037 Uiso 1 1 calc R . . . .
C13 C 0.2168(2) 0.08536(19) 1.40103(16) 0.0298(5) Uani 1 1 d . . . . .
C11 C 0.3255(2) 0.16519(19) 1.19935(16) 0.0296(5) Uani 1 1 d . . . . .
H11 H 0.3811 0.2205 1.1390 0.036 Uiso 1 1 calc R . . . .
C14 C 0.1676(2) -0.00283(19) 1.38037(17) 0.0324(5) Uani 1 1 d . . . . .
H14 H 0.1167 -0.0602 1.4417 0.039 Uiso 1 1 calc R . . . .
C19 C 0.5014(3) 0.49402(19) 0.86096(18) 0.0373(5) Uani 1 1 d . . . . .
C17 C 0.5550(2) 0.2851(2) 0.88562(18) 0.0351(5) Uani 1 1 d . . . . .
H17 H 0.6248 0.2156 0.8829 0.042 Uiso 1 1 calc R . . . .
C18 C 0.6054(3) 0.3934(2) 0.8553(2) 0.0455(6) Uani 1 1 d . . . . .
H18 H 0.7085 0.3976 0.8316 0.055 Uiso 1 1 calc R . . . .
C20 C 0.3496(3) 0.49215(19) 0.89516(18) 0.0371(5) Uani 1 1 d . . . . .
H20 H 0.2809 0.5620 0.8991 0.045 Uiso 1 1 calc R . . . .
O6 O 0.92154(15) 0.45049(15) 0.29389(11) 0.0367(4) Uani 1 1 d . . . . .
H6 H 0.9618 0.4304 0.3468 0.055 Uiso 1 1 calc GR . . . .
C30 C 1.0305(2) 0.4811(2) 0.18655(18) 0.0459(6) Uani 1 1 d . . . . .
H30A H 1.0033 0.4626 0.1285 0.069 Uiso 1 1 calc GR . . . .
H30B H 1.1275 0.4363 0.1934 0.069 Uiso 1 1 calc GR . . . .
H30C H 1.0353 0.5653 0.1643 0.069 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
O5 H5 0.8200 . ?
O5 C29 1.320(2) . ?
O3 C28 1.214(2) . ?
F1 C6 1.362(2) . ?
O2 H2 0.8200 . ?
O2 C28 1.328(2) . ?
F2 C13 1.358(2) . ?
O1 H1 0.8200 . ?
O1 C3 1.356(2) . ?
O4 C29 1.214(2) . ?
N8 C7 1.321(2) . ?
N8 C8 1.382(2) . ?
N10 C22 1.441(2) . ?
N10 C7 1.376(2) . ?
N10 C9 1.401(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.392(3) . ?
C25 C24 1.388(3) . ?
C10 C8 1.474(3) . ?
C10 C15 1.397(3) . ?
C10 C11 1.391(3) . ?
C26 C27 1.390(2) . ?
C26 C28 1.488(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.388(2) . ?
C23 C22 1.385(3) . ?
C4 C7 1.464(3) . ?
C4 C3 1.416(3) . ?
C4 C5 1.400(3) . ?
C27 H27 0.9300 . ?
C27 C22 1.382(3) . ?
C24 C29 1.487(3) . ?
F3 C19 1.362(3) . ?
C8 C9 1.373(2) . ?
C9 C16 1.477(3) . ?
C3 C2 1.388(3) . ?
C5 H5A 0.9300 . ?
C5 C6 1.370(3) . ?
C16 C21 1.380(3) . ?
C16 C17 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.381(3) . ?
C6 C1 1.376(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(3) . ?
C12 C11 1.383(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.375(3) . ?
C2 H2A 0.9300 . ?
C13 C14 1.382(3) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C19 C18 1.362(3) . ?
C19 C20 1.361(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
O6 H6 0.8200 . ?
O6 C30 1.402(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C29 O5 H5 109.5 . . ?
C28 O2 H2 109.5 . . ?
C3 O1 H1 109.5 . . ?
C7 N8 C8 107.40(15) . . ?
C7 N10 C22 127.61(16) . . ?
C7 N10 C9 107.15(14) . . ?
C9 N10 C22 123.33(15) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.82(16) . . ?
C15 C10 C8 119.78(18) . . ?
C11 C10 C8 122.40(17) . . ?
C11 C10 C15 117.79(17) . . ?
C25 C26 C28 118.69(16) . . ?
C27 C26 C25 120.20(17) . . ?
C27 C26 C28 121.09(16) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.75(17) . . ?
C3 C4 C7 118.46(16) . . ?
C5 C4 C7 123.05(18) . . ?
C5 C4 C3 118.47(18) . . ?
C26 C27 H27 120.3 . . ?
C22 C27 C26 119.41(17) . . ?
C22 C27 H27 120.3 . . ?
C25 C24 C29 122.55(16) . . ?
C23 C24 C25 119.96(17) . . ?
C23 C24 C29 117.50(17) . . ?
C23 C22 N10 119.55(16) . . ?
C27 C22 N10 119.64(16) . . ?
C27 C22 C23 120.78(16) . . ?
N8 C7 N10 110.29(17) . . ?
N8 C7 C4 122.88(17) . . ?
N10 C7 C4 126.83(16) . . ?
N8 C8 C10 120.18(16) . . ?
C9 C8 N8 109.46(16) . . ?
C9 C8 C10 130.29(18) . . ?
N10 C9 C16 121.23(14) . . ?
C8 C9 N10 105.70(16) . . ?
C8 C9 C16 133.01(17) . . ?
O3 C28 O2 123.84(18) . . ?
O3 C28 C26 122.90(17) . . ?
O2 C28 C26 113.25(15) . . ?
O1 C3 C4 122.56(18) . . ?
O1 C3 C2 118.07(18) . . ?
C2 C3 C4 119.35(18) . . ?
O5 C29 C24 114.55(17) . . ?
O4 C29 O5 123.11(18) . . ?
O4 C29 C24 122.34(17) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 C4 119.55(19) . . ?
C6 C5 H5A 120.2 . . ?
C21 C16 C9 120.58(18) . . ?
C21 C16 C17 118.29(19) . . ?
C17 C16 C9 121.12(17) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
F1 C6 C5 118.47(19) . . ?
F1 C6 C1 118.97(19) . . ?
C5 C6 C1 122.56(19) . . ?
C16 C21 H21 119.3 . . ?
C16 C21 C20 121.4(2) . . ?
C20 C21 H21 119.3 . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C6 C1 H1A 120.9 . . ?
C2 C1 C6 118.3(2) . . ?
C2 C1 H1A 120.9 . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 C3 121.4(2) . . ?
C1 C2 H2A 119.3 . . ?
F2 C13 C12 119.3(2) . . ?
F2 C13 C14 118.77(18) . . ?
C12 C13 C14 121.97(18) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.34(19) . . ?
C12 C11 H11 119.3 . . ?
C15 C14 C13 118.46(19) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
F3 C19 C18 118.8(2) . . ?
C20 C19 F3 118.6(2) . . ?
C20 C19 C18 122.6(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 118.7(2) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C21 C20 H20 120.9 . . ?
C19 C20 C21 118.1(2) . . ?
C19 C20 H20 120.9 . . ?
C30 O6 H6 109.5 . . ?
O6 C30 H30A 109.5 . . ?
O6 C30 H30B 109.5 . . ?
O6 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
F1 C6 C1 C2 176.14(18) . . . . ?
F2 C13 C14 C15 177.03(17) . . . . ?
O1 C3 C2 C1 -176.84(18) . . . . ?
N8 C8 C9 N10 0.20(19) . . . . ?
N8 C8 C9 C16 177.54(19) . . . . ?
N10 C9 C16 C21 93.9(2) . . . . ?
N10 C9 C16 C17 -84.8(2) . . . . ?
C25 C26 C27 C22 -1.8(3) . . . . ?
C25 C26 C28 O3 4.7(3) . . . . ?
C25 C26 C28 O2 -175.89(17) . . . . ?
C25 C24 C29 O5 -3.1(3) . . . . ?
C25 C24 C29 O4 176.0(2) . . . . ?
C10 C8 C9 N10 -176.66(17) . . . . ?
C10 C8 C9 C16 0.7(3) . . . . ?
C10 C15 C14 C13 0.8(3) . . . . ?
C26 C25 C24 C23 2.3(3) . . . . ?
C26 C25 C24 C29 -177.32(17) . . . . ?
C26 C27 C22 N10 178.72(16) . . . . ?
C26 C27 C22 C23 0.8(3) . . . . ?
C23 C24 C29 O5 177.30(16) . . . . ?
C23 C24 C29 O4 -3.6(3) . . . . ?
C4 C3 C2 C1 4.4(3) . . . . ?
C4 C5 C6 F1 -177.90(17) . . . . ?
C4 C5 C6 C1 2.5(3) . . . . ?
C27 C26 C28 O3 -173.95(18) . . . . ?
C27 C26 C28 O2 5.5(3) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C24 C25 C26 C28 -178.37(17) . . . . ?
C24 C23 C22 N10 -176.18(17) . . . . ?
C24 C23 C22 C27 1.7(3) . . . . ?
C22 N10 C7 N8 -164.35(16) . . . . ?
C22 N10 C7 C4 14.6(3) . . . . ?
C22 N10 C9 C8 165.11(16) . . . . ?
C22 N10 C9 C16 -12.6(3) . . . . ?
C22 C23 C24 C25 -3.3(3) . . . . ?
C22 C23 C24 C29 176.36(17) . . . . ?
F3 C19 C18 C17 -179.5(2) . . . . ?
F3 C19 C20 C21 178.69(18) . . . . ?
C7 N8 C8 C10 177.10(16) . . . . ?
C7 N8 C8 C9 -0.1(2) . . . . ?
C7 N10 C22 C23 -130.0(2) . . . . ?
C7 N10 C22 C27 52.1(3) . . . . ?
C7 N10 C9 C8 -0.19(18) . . . . ?
C7 N10 C9 C16 -177.93(17) . . . . ?
C7 C4 C3 O1 -3.3(3) . . . . ?
C7 C4 C3 C2 175.32(17) . . . . ?
C7 C4 C5 C6 -178.73(18) . . . . ?
C8 N8 C7 N10 0.0(2) . . . . ?
C8 N8 C7 C4 -178.98(16) . . . . ?
C8 C10 C15 C14 -176.62(17) . . . . ?
C8 C10 C11 C12 175.52(18) . . . . ?
C8 C9 C16 C21 -83.1(3) . . . . ?
C8 C9 C16 C17 98.2(3) . . . . ?
C9 N10 C22 C23 67.9(2) . . . . ?
C9 N10 C22 C27 -110.0(2) . . . . ?
C9 N10 C7 N8 0.13(19) . . . . ?
C9 N10 C7 C4 179.06(17) . . . . ?
C9 C16 C21 C20 -179.11(18) . . . . ?
C9 C16 C17 C18 178.29(19) . . . . ?
C28 C26 C27 C22 176.78(17) . . . . ?
C3 C4 C7 N8 22.3(3) . . . . ?
C3 C4 C7 N10 -156.47(18) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
C5 C4 C7 N8 -156.18(18) . . . . ?
C5 C4 C7 N10 25.0(3) . . . . ?
C5 C4 C3 O1 175.24(17) . . . . ?
C5 C4 C3 C2 -6.1(3) . . . . ?
C5 C6 C1 C2 -4.2(3) . . . . ?
C16 C21 C20 C19 0.9(3) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C15 C10 C8 N8 -6.9(3) . . . . ?
C15 C10 C8 C9 169.71(19) . . . . ?
C15 C10 C11 C12 -2.5(3) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C21 C16 C17 C18 -0.5(3) . . . . ?
C12 C13 C14 C15 -2.1(3) . . . . ?
C13 C12 C11 C10 1.3(3) . . . . ?
C11 C10 C8 N8 175.14(18) . . . . ?
C11 C10 C8 C9 -8.3(3) . . . . ?
C11 C10 C15 C14 1.5(3) . . . . ?
C11 C12 C13 F2 -178.04(17) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C17 C16 C21 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C20 C19 C18 C17 0.0(4) . . . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1470805'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-06-26 downloaded from the CCDC.
;
_audit_creation_date             2015-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C29 H17 F3 N2 O5, 2(C3 H7 N O)'
_chemical_formula_sum            'C35 H31 F3 N4 O7'
_chemical_formula_weight         676.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.3694(3)
_cell_length_b                   12.9551(5)
_cell_length_c                   13.3347(5)
_cell_angle_alpha                87.150(3)
_cell_angle_beta                 86.739(3)
_cell_angle_gamma                66.714(3)
_cell_volume                     1642.03(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9226
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1030
_cell_measurement_theta_min      3.2960
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18599
_diffrn_reflns_theta_full        74.22
_diffrn_reflns_theta_max         74.22
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                5491
_reflns_number_total             6494
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         6494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1099
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.64634(10) 0.09956(8) 0.33473(7) 0.0452(2) Uani 1 d . . .
O2 O 0.69810(11) 0.03043(9) 0.49095(7) 0.0483(3) Uani 1 d . . .
N3 N 1.13064(12) -0.05817(9) 0.14865(7) 0.0338(2) Uani 1 d . . .
O4 O 1.14593(11) -0.24636(10) 0.57140(7) 0.0528(3) Uani 1 d . . .
O5 O 1.32144(11) -0.31258(9) 0.45689(8) 0.0528(3) Uani 1 d . . .
C6 C 0.93373(14) -0.01126(10) 0.27185(9) 0.0334(3) Uani 1 d . . .
O7 O 1.55535(12) -0.14939(10) 0.45061(8) 0.0554(3) Uani 1 d . . .
N8 N 1.23487(12) -0.08842(10) -0.00234(8) 0.0379(2) Uani 1 d . . .
O9 O 1.34755(13) -0.29156(11) -0.06608(9) 0.0595(3) Uani 1 d . . .
C10 C 0.88070(13) -0.02587(10) 0.36751(9) 0.0329(3) Uani 1 d . . .
F11 F 1.07700(12) 0.38504(9) 0.37850(8) 0.0690(3) Uani 1 d . . .
C12 C 1.16056(14) -0.15317(10) 0.31292(9) 0.0339(3) Uani 1 d . . .
F13 F 0.94571(13) -0.38993(9) 0.15056(9) 0.0724(3) Uani 1 d . . .
C14 C 0.96829(14) -0.10263(10) 0.43585(9) 0.0333(3) Uani 1 d . . .
O15 O 0.68556(13) 0.38996(10) 0.30485(8) 0.0568(3) Uani 1 d . . .
C16 C 1.07283(14) -0.07535(10) 0.24586(9) 0.0324(3) Uani 1 d . . .
C17 C 0.72978(14) 0.04125(10) 0.39532(9) 0.0353(3) Uani 1 d . . .
C18 C 1.10743(13) -0.16677(10) 0.40844(9) 0.0331(3) Uani 1 d . . .
C19 C 1.23652(14) 0.00999(11) 0.03104(9) 0.0357(3) Uani 1 d . . .
F20 F 1.50817(14) 0.23482(11) -0.20971(9) 0.0808(4) Uani 1 d . . .
C21 C 1.14449(14) 0.12295(11) 0.19427(9) 0.0339(3) Uani 1 d . . .
C22 C 1.17153(14) -0.12825(11) 0.06912(9) 0.0350(3) Uani 1 d . . .
C23 C 1.20366(14) -0.25009(11) 0.48070(10) 0.0373(3) Uani 1 d . . .
C24 C 1.04724(17) -0.36514(13) 0.09892(11) 0.0474(3) Uani 1 d . . .
C25 C 1.30586(14) 0.07224(11) -0.03079(9) 0.0370(3) Uani 1 d . . .
C26 C 1.34590(15) 0.04242(13) -0.13062(10) 0.0426(3) Uani 1 d . . .
C27 C 1.17152(14) 0.03084(11) 0.12497(9) 0.0340(3) Uani 1 d . . .
C28 C 1.15657(14) -0.23528(11) 0.05986(9) 0.0363(3) Uani 1 d . . .
C29 C 1.05379(16) -0.26283(12) 0.11301(10) 0.0419(3) Uani 1 d . . .
C30 C 1.21929(15) 0.10546(12) 0.28156(10) 0.0397(3) Uani 1 d . . .
C31 C 1.02361(17) 0.31894(13) 0.23256(12) 0.0475(3) Uani 1 d . . .
N32 N 0.46866(14) 0.42396(11) 0.25165(9) 0.0494(3) Uani 1 d . . .
C33 C 1.04665(16) 0.23005(12) 0.17126(10) 0.0424(3) Uani 1 d . . .
C34 C 1.19716(17) 0.19385(13) 0.34385(10) 0.0448(3) Uani 1 d . . .
C35 C 1.09973(17) 0.29792(13) 0.31743(11) 0.0457(3) Uani 1 d . . .
C36 C 1.41304(17) 0.09743(15) -0.19140(11) 0.0502(4) Uani 1 d . . .
C37 C 1.24837(15) -0.31302(12) -0.00889(10) 0.0425(3) Uani 1 d . . .
C38 C 1.23816(17) -0.41586(13) -0.02007(12) 0.0489(3) Uani 1 d . . .
C39 C 1.13808(18) -0.44276(13) 0.03410(12) 0.0499(4) Uani 1 d . . .
C40 C 1.44055(17) 0.18097(14) -0.15121(12) 0.0527(4) Uani 1 d . . .
N41 N 1.69579(16) -0.33437(12) 0.44612(11) 0.0589(4) Uani 1 d . . .
C42 C 1.33711(17) 0.15781(13) 0.00686(11) 0.0465(3) Uani 1 d . . .
C43 C 0.59264(17) 0.35853(13) 0.28472(11) 0.0469(3) Uani 1 d . . .
C44 C 1.58129(17) -0.24864(14) 0.47314(12) 0.0506(4) Uani 1 d . . .
C45 C 1.40446(18) 0.21318(15) -0.05343(13) 0.0538(4) Uani 1 d . . .
C46 C 0.4323(3) 0.54277(17) 0.2335(2) 0.0744(6) Uani 1 d . . .
C47 C 1.7138(3) -0.44906(18) 0.4785(2) 0.0954(8) Uani 1 d . . .
H47A H 1.6314 -0.4469 0.5166 0.143 Uiso 1 calc . . GR
H47B H 1.7941 -0.4813 0.5195 0.143 Uiso 1 calc . . GR
H47C H 1.7277 -0.4939 0.4206 0.143 Uiso 1 calc . . GR
C48 C 0.3718(3) 0.3760(3) 0.2225(2) 0.0857(7) Uani 1 d . . .
C49 C 1.8044(3) -0.3177(2) 0.38318(19) 0.1034(10) Uani 1 d . . .
H49A H 1.8076 -0.3474 0.3181 0.155 Uiso 1 calc . . GR
H49B H 1.8935 -0.3557 0.4134 0.155 Uiso 1 calc . . GR
H49C H 1.7843 -0.2387 0.3762 0.155 Uiso 1 calc . . GR
H12 H 1.2594(18) -0.1969(14) 0.2927(12) 0.041(4) Uiso 1 d . . .
H14 H 0.9329(17) -0.1108(13) 0.4980(13) 0.042(4) Uiso 1 d . . .
H6 H 0.8733(17) 0.0434(14) 0.2251(12) 0.043(4) Uiso 1 d . . .
H33 H 0.996(2) 0.2435(16) 0.1099(15) 0.060(5) Uiso 1 d . . .
H29 H 0.9838(19) -0.2098(15) 0.1575(14) 0.052(5) Uiso 1 d . . .
H26 H 1.3258(17) -0.0179(14) -0.1589(12) 0.043(4) Uiso 1 d . . .
H30 H 1.2902(18) 0.0299(15) 0.2971(12) 0.046(4) Uiso 1 d . . .
H42 H 1.313(2) 0.1787(16) 0.0773(15) 0.058(5) Uiso 1 d . . .
H34 H 1.248(2) 0.1844(16) 0.4062(14) 0.058(5) Uiso 1 d . . .
H31 H 0.958(2) 0.3876(17) 0.2152(15) 0.063(5) Uiso 1 d . . .
H39 H 1.129(2) -0.5144(17) 0.0290(14) 0.062(5) Uiso 1 d . . .
H43 H 0.606(2) 0.2794(17) 0.2946(14) 0.062(5) Uiso 1 d . . .
H36 H 1.438(2) 0.0765(17) -0.2582(16) 0.069(6) Uiso 1 d . . .
H45 H 1.430(2) 0.2730(18) -0.0224(16) 0.073(6) Uiso 1 d . . .
H38 H 1.3054(19) -0.4695(16) -0.0670(14) 0.055(5) Uiso 1 d . . .
H44 H 1.515(2) -0.268(2) 0.5128(18) 0.083(7) Uiso 1 d . . .
H4 H 1.213(3) -0.302(2) 0.6151(19) 0.094(8) Uiso 1 d . . .
H2 H 0.600(3) 0.076(2) 0.5050(18) 0.087(7) Uiso 1 d . . .
H46A H 0.501(3) 0.565(2) 0.257(2) 0.098(9) Uiso 1 d . . .
H9 H 1.332(2) -0.216(2) -0.0596(17) 0.078(7) Uiso 1 d . . .
H48A H 0.411(3) 0.294(3) 0.248(2) 0.120(10) Uiso 1 d . . .
H46B H 0.427(3) 0.560(3) 0.164(3) 0.119(10) Uiso 1 d . . .
H48B H 0.358(4) 0.385(3) 0.146(3) 0.140(12) Uiso 1 d . . .
H48C H 0.283(3) 0.422(3) 0.259(2) 0.111(10) Uiso 1 d . . .
H46C H 0.340(4) 0.585(3) 0.255(3) 0.146(13) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.2141(16) . ?
O2 C17 1.3134(16) . ?
O2 H2 0.97(3) . ?
N3 C16 1.4414(15) . ?
N3 C22 1.3671(16) . ?
N3 C27 1.3943(16) . ?
O4 C23 1.3130(16) . ?
O4 H4 0.97(3) . ?
O5 C23 1.2031(17) . ?
C6 C10 1.3943(17) . ?
C6 C16 1.3837(18) . ?
C6 H6 0.965(17) . ?
O7 C44 1.230(2) . ?
N8 C19 1.3778(17) . ?
N8 C22 1.3242(16) . ?
O9 C37 1.3536(18) . ?
O9 H9 0.93(2) . ?
C10 C14 1.3907(17) . ?
C10 C17 1.4943(18) . ?
F11 C35 1.3608(16) . ?
C12 C16 1.3861(18) . ?
C12 C18 1.3899(17) . ?
C12 H12 0.984(17) . ?
F13 C24 1.3597(18) . ?
C14 C18 1.3885(18) . ?
C14 H14 0.906(17) . ?
O15 C43 1.231(2) . ?
C18 C23 1.4979(17) . ?
C19 C25 1.4738(17) . ?
C19 C27 1.3747(17) . ?
F20 C40 1.3628(16) . ?
C21 C27 1.4738(17) . ?
C21 C30 1.3948(18) . ?
C21 C33 1.3888(19) . ?
C22 C28 1.4667(18) . ?
C24 C29 1.376(2) . ?
C24 C39 1.375(2) . ?
C25 C26 1.3983(19) . ?
C25 C42 1.394(2) . ?
C26 C36 1.386(2) . ?
C26 H26 0.981(17) . ?
C28 C29 1.3983(19) . ?
C28 C37 1.4126(19) . ?
C29 H29 0.974(19) . ?
C30 C34 1.385(2) . ?
C30 H30 0.985(17) . ?
C31 C33 1.380(2) . ?
C31 C35 1.371(2) . ?
C31 H31 0.91(2) . ?
N32 C43 1.316(2) . ?
N32 C46 1.444(2) . ?
N32 C48 1.452(3) . ?
C33 H33 0.97(2) . ?
C34 C35 1.371(2) . ?
C34 H34 0.986(19) . ?
C36 C40 1.363(2) . ?
C36 H36 0.94(2) . ?
C37 C38 1.393(2) . ?
C38 C39 1.377(2) . ?
C38 H38 0.985(19) . ?
C39 H39 0.97(2) . ?
C40 C45 1.375(2) . ?
N41 C44 1.312(2) . ?
N41 C47 1.468(3) . ?
N41 C49 1.445(3) . ?
C42 C45 1.387(2) . ?
C42 H42 0.981(19) . ?
C43 H43 0.98(2) . ?
C44 H44 0.95(2) . ?
C45 H45 1.02(2) . ?
C46 H46A 0.94(3) . ?
C46 H46B 0.94(3) . ?
C46 H46C 0.93(4) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 H48A 1.02(3) . ?
C48 H48B 1.03(4) . ?
C48 H48C 0.99(3) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 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 O2 H2 109.8(14) . . ?
C22 N3 C16 128.56(10) . . ?
C22 N3 C27 107.43(10) . . ?
C27 N3 C16 123.55(10) . . ?
C23 O4 H4 109.4(15) . . ?
C10 C6 H6 119.7(9) . . ?
C16 C6 C10 119.14(11) . . ?
C16 C6 H6 121.2(9) . . ?
C22 N8 C19 107.42(10) . . ?
C37 O9 H9 108.1(14) . . ?
C6 C10 C17 119.42(11) . . ?
C14 C10 C6 119.85(12) . . ?
C14 C10 C17 120.73(11) . . ?
C16 C12 C18 119.13(12) . . ?
C16 C12 H12 119.8(9) . . ?
C18 C12 H12 121.1(9) . . ?
C10 C14 H14 119.0(10) . . ?
C18 C14 C10 120.31(11) . . ?
C18 C14 H14 120.6(10) . . ?
C6 C16 N3 119.78(11) . . ?
C6 C16 C12 121.49(11) . . ?
C12 C16 N3 118.68(11) . . ?
O1 C17 O2 124.20(12) . . ?
O1 C17 C10 122.67(11) . . ?
O2 C17 C10 113.13(11) . . ?
C12 C18 C23 118.67(11) . . ?
C14 C18 C12 120.07(11) . . ?
C14 C18 C23 121.26(11) . . ?
N8 C19 C25 120.30(11) . . ?
C27 C19 N8 109.17(11) . . ?
C27 C19 C25 130.49(12) . . ?
C30 C21 C27 121.03(12) . . ?
C33 C21 C27 119.93(11) . . ?
C33 C21 C30 119.00(12) . . ?
N3 C22 C28 127.93(11) . . ?
N8 C22 N3 110.18(11) . . ?
N8 C22 C28 121.86(11) . . ?
O4 C23 C18 112.85(11) . . ?
O5 C23 O4 124.47(12) . . ?
O5 C23 C18 122.68(12) . . ?
F13 C24 C29 118.55(14) . . ?
F13 C24 C39 118.67(13) . . ?
C39 C24 C29 122.78(15) . . ?
C26 C25 C19 118.89(12) . . ?
C42 C25 C19 122.75(12) . . ?
C42 C25 C26 118.34(13) . . ?
C25 C26 H26 120.0(10) . . ?
C36 C26 C25 121.06(14) . . ?
C36 C26 H26 118.9(10) . . ?
N3 C27 C21 122.34(10) . . ?
C19 C27 N3 105.80(11) . . ?
C19 C27 C21 131.86(11) . . ?
C29 C28 C22 123.55(12) . . ?
C29 C28 C37 118.42(12) . . ?
C37 C28 C22 118.00(12) . . ?
C24 C29 C28 119.43(14) . . ?
C24 C29 H29 119.1(10) . . ?
C28 C29 H29 121.4(10) . . ?
C21 C30 H30 119.0(10) . . ?
C34 C30 C21 120.46(13) . . ?
C34 C30 H30 120.5(10) . . ?
C33 C31 H31 118.4(13) . . ?
C35 C31 C33 117.82(14) . . ?
C35 C31 H31 123.8(13) . . ?
C43 N32 C46 120.71(17) . . ?
C43 N32 C48 120.36(17) . . ?
C46 N32 C48 118.61(18) . . ?
C21 C33 H33 119.6(12) . . ?
C31 C33 C21 121.17(13) . . ?
C31 C33 H33 119.2(12) . . ?
C30 C34 H34 122.6(11) . . ?
C35 C34 C30 118.15(13) . . ?
C35 C34 H34 119.2(11) . . ?
F11 C35 C31 118.13(14) . . ?
F11 C35 C34 118.48(13) . . ?
C34 C35 C31 123.39(13) . . ?
C26 C36 H36 119.6(13) . . ?
C40 C36 C26 118.36(14) . . ?
C40 C36 H36 122.1(13) . . ?
O9 C37 C28 122.38(13) . . ?
O9 C37 C38 117.63(13) . . ?
C38 C37 C28 120.00(14) . . ?
C37 C38 H38 118.3(11) . . ?
C39 C38 C37 120.96(14) . . ?
C39 C38 H38 120.7(11) . . ?
C24 C39 C38 118.39(14) . . ?
C24 C39 H39 118.6(12) . . ?
C38 C39 H39 123.0(12) . . ?
F20 C40 C36 119.01(15) . . ?
F20 C40 C45 117.96(15) . . ?
C36 C40 C45 123.03(14) . . ?
C44 N41 C47 120.08(19) . . ?
C44 N41 C49 120.75(17) . . ?
C49 N41 C47 119.17(19) . . ?
C25 C42 H42 120.2(11) . . ?
C45 C42 C25 120.95(14) . . ?
C45 C42 H42 118.8(11) . . ?
O15 C43 N32 125.35(15) . . ?
O15 C43 H43 120.9(11) . . ?
N32 C43 H43 113.7(11) . . ?
O7 C44 N41 125.57(16) . . ?
O7 C44 H44 119.8(14) . . ?
N41 C44 H44 114.6(14) . . ?
C40 C45 C42 118.26(15) . . ?
C40 C45 H45 122.8(12) . . ?
C42 C45 H45 118.8(12) . . ?
N32 C46 H46A 111.5(17) . . ?
N32 C46 H46B 110(2) . . ?
N32 C46 H46C 111(2) . . ?
H46A C46 H46B 107(2) . . ?
H46A C46 H46C 116(3) . . ?
H46B C46 H46C 101(3) . . ?
N41 C47 H47A 109.5 . . ?
N41 C47 H47B 109.5 . . ?
N41 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N32 C48 H48A 106.4(18) . . ?
N32 C48 H48B 111(2) . . ?
N32 C48 H48C 102.8(18) . . ?
H48A C48 H48B 113(3) . . ?
H48A C48 H48C 112(2) . . ?
H48B C48 H48C 110(3) . . ?
N41 C49 H49A 109.5 . . ?
N41 C49 H49B 109.5 . . ?
N41 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 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
N3 C22 C28 C29 25.1(2) . . . . ?
N3 C22 C28 C37 -156.93(13) . . . . ?
C6 C10 C14 C18 -1.58(18) . . . . ?
C6 C10 C17 O1 8.30(19) . . . . ?
C6 C10 C17 O2 -171.61(11) . . . . ?
N8 C19 C25 C26 12.02(19) . . . . ?
N8 C19 C25 C42 -166.07(13) . . . . ?
N8 C19 C27 N3 0.38(14) . . . . ?
N8 C19 C27 C21 179.97(13) . . . . ?
N8 C22 C28 C29 -157.41(13) . . . . ?
N8 C22 C28 C37 20.55(19) . . . . ?
O9 C37 C38 C39 -178.74(14) . . . . ?
C10 C6 C16 N3 -177.62(10) . . . . ?
C10 C6 C16 C12 -0.33(18) . . . . ?
C10 C14 C18 C12 1.09(19) . . . . ?
C10 C14 C18 C23 -179.90(11) . . . . ?
C12 C18 C23 O4 172.92(12) . . . . ?
C12 C18 C23 O5 -6.6(2) . . . . ?
F13 C24 C29 C28 -179.37(13) . . . . ?
F13 C24 C39 C38 178.21(14) . . . . ?
C14 C10 C17 O1 -171.57(12) . . . . ?
C14 C10 C17 O2 8.51(17) . . . . ?
C14 C18 C23 O4 -6.10(18) . . . . ?
C14 C18 C23 O5 174.38(13) . . . . ?
C16 N3 C22 N8 -172.43(12) . . . . ?
C16 N3 C22 C28 5.3(2) . . . . ?
C16 N3 C27 C19 172.64(11) . . . . ?
C16 N3 C27 C21 -7.01(19) . . . . ?
C16 C6 C10 C14 1.20(18) . . . . ?
C16 C6 C10 C17 -178.68(11) . . . . ?
C16 C12 C18 C14 -0.22(18) . . . . ?
C16 C12 C18 C23 -179.25(11) . . . . ?
C17 C10 C14 C18 178.29(11) . . . . ?
C18 C12 C16 N3 177.16(11) . . . . ?
C18 C12 C16 C6 -0.16(18) . . . . ?
C19 N8 C22 N3 0.33(15) . . . . ?
C19 N8 C22 C28 -177.55(12) . . . . ?
C19 C25 C26 C36 -179.16(14) . . . . ?
C19 C25 C42 C45 178.99(14) . . . . ?
F20 C40 C45 C42 -179.25(16) . . . . ?
C21 C30 C34 C35 0.4(2) . . . . ?
C22 N3 C16 C6 -110.73(15) . . . . ?
C22 N3 C16 C12 71.91(17) . . . . ?
C22 N3 C27 C19 -0.18(14) . . . . ?
C22 N3 C27 C21 -179.82(12) . . . . ?
C22 N8 C19 C25 177.47(12) . . . . ?
C22 N8 C19 C27 -0.44(15) . . . . ?
C22 C28 C29 C24 179.57(13) . . . . ?
C22 C28 C37 O9 -0.5(2) . . . . ?
C22 C28 C37 C38 179.89(13) . . . . ?
C25 C19 C27 N3 -177.25(13) . . . . ?
C25 C19 C27 C21 2.3(2) . . . . ?
C25 C26 C36 C40 0.6(2) . . . . ?
C25 C42 C45 C40 -0.4(3) . . . . ?
C26 C25 C42 C45 0.9(2) . . . . ?
C26 C36 C40 F20 179.15(15) . . . . ?
C26 C36 C40 C45 -0.2(3) . . . . ?
C27 N3 C16 C6 78.05(16) . . . . ?
C27 N3 C16 C12 -99.31(14) . . . . ?
C27 N3 C22 N8 -0.10(14) . . . . ?
C27 N3 C22 C28 177.62(13) . . . . ?
C27 C19 C25 C26 -170.58(14) . . . . ?
C27 C19 C25 C42 11.3(2) . . . . ?
C27 C21 C30 C34 177.21(12) . . . . ?
C27 C21 C33 C31 -177.17(13) . . . . ?
C28 C37 C38 C39 0.9(2) . . . . ?
C29 C24 C39 C38 -1.1(2) . . . . ?
C29 C28 C37 O9 177.59(13) . . . . ?
C29 C28 C37 C38 -2.0(2) . . . . ?
C30 C21 C27 N3 71.95(17) . . . . ?
C30 C21 C27 C19 -107.59(17) . . . . ?
C30 C21 C33 C31 0.6(2) . . . . ?
C30 C34 C35 F11 179.71(13) . . . . ?
C30 C34 C35 C31 -0.2(2) . . . . ?
C33 C21 C27 N3 -110.28(15) . . . . ?
C33 C21 C27 C19 70.2(2) . . . . ?
C33 C21 C30 C34 -0.6(2) . . . . ?
C33 C31 C35 F11 -179.65(13) . . . . ?
C33 C31 C35 C34 0.3(2) . . . . ?
C35 C31 C33 C21 -0.5(2) . . . . ?
C36 C40 C45 C42 0.1(3) . . . . ?
C37 C28 C29 C24 1.6(2) . . . . ?
C37 C38 C39 C24 0.7(2) . . . . ?
C39 C24 C29 C28 -0.1(2) . . . . ?
C42 C25 C26 C36 -1.0(2) . . . . ?
C46 N32 C43 O15 1.5(3) . . . . ?
C47 N41 C44 O7 179.83(18) . . . . ?
C48 N32 C43 O15 174.9(2) . . . . ?
C49 N41 C44 O7 -1.1(3) . . . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1470806'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-06-26 downloaded from the CCDC.
;
_audit_creation_date             2016-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H17 F3 N2 O5, C3 H7 N O, C3 H8 O'
_chemical_formula_sum            'C35 H32 F3 N3 O7'
_chemical_formula_weight         663.63
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1127(3)
_cell_length_b                   12.7452(7)
_cell_length_c                   14.6534(9)
_cell_angle_alpha                89.060(5)
_cell_angle_beta                 89.138(4)
_cell_angle_gamma                69.885(4)
_cell_volume                     1597.79(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2217
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2120
_cell_measurement_theta_min      3.6470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.684
_diffrn_reflns_Laue_measured_fraction_max 0.685
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5205
_diffrn_reflns_point_group_measured_fraction_full 0.684
_diffrn_reflns_point_group_measured_fraction_max 0.685
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.769
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.684
_diffrn_measured_fraction_theta_max 0.685
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3223
_reflns_number_total             4291
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         4291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      0.999
_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)+(0.0639P)²+1.2424P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1473
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C31(H31)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C24(H24), C21(H21), C19(H19), C26(H26), C2(H2), C11(H11), C27(H27),
 C4(H4), C15(H15), C1(H1), C5(H5A), C14(H14), C12(H12), C34(H34)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C33(H33A,H33B,H33C), C32(H32A,H32B,H32C), C30(H30A,H30B,
 H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O7(H7), O5(H5), O2(H2A), 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
N1 N 0.2159(3) 0.87888(19) 0.02185(16) 0.0327(6) Uani 1 1 d . . . . .
O7 O 0.3598(2) 0.66808(18) -0.02088(18) 0.0539(7) Uani 1 1 d . . . . .
H7 H 0.3446 0.7353 -0.0200 0.081 Uiso 1 1 calc GR . . . .
C18 C 0.1369(3) 0.7957(2) 0.3947(2) 0.0375(7) Uani 1 1 d . . . . .
F3 F -0.0968(2) 0.56870(16) 0.16648(16) 0.0696(7) Uani 1 1 d . . . . .
O5 O -0.2753(3) 1.0072(2) 0.50638(16) 0.0565(7) Uani 1 1 d . . . . .
H5 H -0.3608 1.0490 0.5243 0.085 Uiso 1 1 calc GR . . . .
C17 C 0.1718(3) 0.8097(2) 0.30377(19) 0.0331(7) Uani 1 1 d . . . . .
H17 H 0.2647 0.7630 0.2779 0.040 Uiso 1 1 calc R . . . .
N2 N 0.1115(2) 0.91241(18) 0.15989(16) 0.0302(5) Uani 1 1 d . . . . .
C20 C -0.1077(3) 0.9481(2) 0.3799(2) 0.0363(7) Uani 1 1 d . . . . .
C16 C 0.0677(3) 0.8935(2) 0.25179(19) 0.0309(6) Uani 1 1 d . . . . .
C23 C 0.1435(3) 0.7262(2) 0.08675(19) 0.0317(7) Uani 1 1 d . . . . .
C24 C 0.0264(3) 0.6988(2) 0.1320(2) 0.0371(7) Uani 1 1 d . . . . .
H24 H -0.0482 0.7517 0.1670 0.045 Uiso 1 1 calc R . . . .
C21 C -0.0710(3) 0.9620(2) 0.2892(2) 0.0341(7) Uani 1 1 d . . . . .
H21 H -0.1403 1.0178 0.2536 0.041 Uiso 1 1 calc R . . . .
O6 O -0.3573(3) 1.0894(2) 0.37143(18) 0.0616(7) Uani 1 1 d . . . . .
C28 C 0.2491(3) 0.6457(2) 0.0305(2) 0.0363(7) Uani 1 1 d . . . . .
O3 O 0.3641(3) 0.6369(2) 0.41731(18) 0.0652(7) Uani 1 1 d . . . . .
C8 C 0.1559(3) 0.8382(2) 0.08923(19) 0.0290(6) Uani 1 1 d . . . . .
C7 C 0.2116(3) 0.9849(2) 0.0462(2) 0.0311(7) Uani 1 1 d . . . . .
C3 C 0.2792(3) 1.0489(2) -0.0141(2) 0.0327(7) Uani 1 1 d . . . . .
F1 F 0.4959(2) 1.21199(19) -0.18549(17) 0.0712(6) Uani 1 1 d . . . . .
C25 C 0.0219(4) 0.5930(3) 0.1245(2) 0.0439(8) Uani 1 1 d . . . . .
C19 C -0.0030(3) 0.8656(2) 0.4333(2) 0.0399(7) Uani 1 1 d . . . . .
H19 H -0.0260 0.8570 0.4944 0.048 Uiso 1 1 calc R . . . .
C26 C 0.1294(4) 0.5117(2) 0.0741(2) 0.0459(8) Uani 1 1 d . . . . .
H26 H 0.1257 0.4397 0.0723 0.055 Uiso 1 1 calc R . . . .
C2 C 0.3253(3) 1.0120(3) -0.1033(2) 0.0393(7) Uani 1 1 d . . . . .
H2 H 0.3070 0.9490 -0.1239 0.047 Uiso 1 1 calc R . . . .
C10 C 0.1122(3) 1.1055(2) 0.1910(2) 0.0330(7) Uani 1 1 d . . . . .
C22 C -0.2607(4) 1.0229(3) 0.4180(2) 0.0460(8) Uani 1 1 d . . . . .
C11 C 0.1918(4) 1.1005(3) 0.2721(2) 0.0444(8) Uani 1 1 d . . . . .
H11 H 0.2659 1.0336 0.2914 0.053 Uiso 1 1 calc R . . . .
F2 F 0.0233(3) 1.3866(2) 0.3439(2) 0.1076(11) Uani 1 1 d . . . . .
O2 O 0.2256(3) 0.7153(2) 0.53800(17) 0.0710(8) Uani 1 1 d . . . . .
H2A H 0.1574 0.6892 0.5515 0.107 Uiso 1 1 calc GR . . . .
C27 C 0.2423(4) 0.5389(2) 0.0265(2) 0.0454(8) Uani 1 1 d . . . . .
H27 H 0.3151 0.4851 -0.0088 0.054 Uiso 1 1 calc R . . . .
C29 C 0.2523(4) 0.7070(3) 0.4502(2) 0.0475(8) Uani 1 1 d . . . . .
C4 C 0.3067(3) 1.1451(2) 0.0131(2) 0.0415(8) Uani 1 1 d . . . . .
H4 H 0.2768 1.1724 0.0715 0.050 Uiso 1 1 calc R . . . .
C15 C 0.0026(3) 1.2057(2) 0.1632(2) 0.0443(8) Uani 1 1 d . . . . .
H15 H -0.0512 1.2088 0.1092 0.053 Uiso 1 1 calc R . . . .
C9 C 0.1464(3) 1.0067(2) 0.13227(19) 0.0296(6) Uani 1 1 d . . . . .
C13 C 0.0526(5) 1.2928(3) 0.2934(3) 0.0640(12) Uani 1 1 d . . . . .
C1 C 0.3965(4) 1.0663(3) -0.1610(2) 0.0490(8) Uani 1 1 d . . . . .
H1 H 0.4272 1.0402 -0.2196 0.059 Uiso 1 1 calc R . . . .
C5 C 0.3771(3) 1.2001(3) -0.0447(3) 0.0477(9) Uani 1 1 d . . . . .
H5A H 0.3944 1.2641 -0.0256 0.057 Uiso 1 1 calc R . . . .
C14 C -0.0281(4) 1.3009(3) 0.2140(3) 0.0578(11) Uani 1 1 d . . . . .
H14 H -0.1012 1.3684 0.1951 0.069 Uiso 1 1 calc R . . . .
C12 C 0.1602(5) 1.1958(3) 0.3243(3) 0.0628(11) Uani 1 1 d . . . . .
H12 H 0.2113 1.1935 0.3791 0.075 Uiso 1 1 calc R . . . .
C6 C 0.4214(3) 1.1594(3) -0.1305(3) 0.0484(9) Uani 1 1 d . . . . .
N3 N 0.7089(3) 0.6906(3) 0.4347(2) 0.0566(8) Uani 1 1 d . . . . .
O4 O 0.5252(3) 0.8609(2) 0.4199(2) 0.0730(8) Uani 1 1 d . . . . .
C34 C 0.5889(4) 0.7729(3) 0.4636(3) 0.0582(10) Uani 1 1 d . . . . .
H34 H 0.5479 0.7655 0.5208 0.070 Uiso 1 1 calc R . . . .
C35 C 0.7776(5) 0.6940(4) 0.3457(3) 0.0801(14) Uani 1 1 d . . . . .
H35A H 0.7485 0.6463 0.3050 0.120 Uiso 1 1 calc GR . . . .
H35B H 0.8893 0.6687 0.3506 0.120 Uiso 1 1 calc GR . . . .
H35C H 0.7405 0.7692 0.3222 0.120 Uiso 1 1 calc GR . . . .
C33 C 0.7702(7) 0.5873(5) 0.4846(4) 0.113(2) Uani 1 1 d . . . . .
H33A H 0.8769 0.5746 0.5003 0.170 Uiso 1 1 calc GR . . . .
H33B H 0.7653 0.5271 0.4476 0.170 Uiso 1 1 calc GR . . . .
H33C H 0.7094 0.5910 0.5393 0.170 Uiso 1 1 calc GR . . . .
O1 O 0.4521(4) 0.5798(3) 0.6326(2) 0.0998(12) Uani 1 1 d . . . . .
H1A H 0.3630 0.5828 0.6210 0.150 Uiso 1 1 calc GR . . . .
C32 C 0.4736(6) 0.4950(3) 0.7831(3) 0.0765(12) Uani 1 1 d . . . . .
H32A H 0.3948 0.4667 0.7628 0.115 Uiso 1 1 calc GR . . . .
H32B H 0.4570 0.5132 0.8466 0.115 Uiso 1 1 calc GR . . . .
H32C H 0.5749 0.4392 0.7747 0.115 Uiso 1 1 calc GR . . . .
C31 C 0.4643(6) 0.5962(4) 0.7298(3) 0.0828(14) Uani 1 1 d . . . . .
H31 H 0.3604 0.6486 0.7457 0.099 Uiso 1 1 calc R . . . .
C30 C 0.5624(9) 0.6554(6) 0.7502(5) 0.148(3) Uani 1 1 d . . . . .
H30A H 0.6683 0.6113 0.7350 0.223 Uiso 1 1 calc GR . . . .
H30B H 0.5547 0.6716 0.8142 0.223 Uiso 1 1 calc GR . . . .
H30C H 0.5318 0.7240 0.7157 0.223 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
N1 C8 1.305(4) . ?
N1 C7 1.390(3) . ?
O7 H7 0.8200 . ?
O7 C28 1.354(4) . ?
C18 C17 1.388(4) . ?
C18 C19 1.397(4) . ?
C18 C29 1.492(5) . ?
F3 C25 1.359(3) . ?
O5 H5 0.8200 . ?
O5 C22 1.319(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.386(4) . ?
N2 C16 1.439(4) . ?
N2 C8 1.374(3) . ?
N2 C9 1.398(4) . ?
C20 C21 1.390(4) . ?
C20 C19 1.391(4) . ?
C20 C22 1.497(4) . ?
C16 C21 1.377(4) . ?
C23 C24 1.388(4) . ?
C23 C28 1.408(4) . ?
C23 C8 1.471(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.370(4) . ?
C21 H21 0.9300 . ?
O6 C22 1.202(4) . ?
C28 C27 1.387(4) . ?
O3 C29 1.200(4) . ?
C7 C3 1.459(4) . ?
C7 C9 1.377(4) . ?
C3 C2 1.406(4) . ?
C3 C4 1.398(4) . ?
F1 C6 1.356(4) . ?
C25 C26 1.372(4) . ?
C19 H19 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.372(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.374(5) . ?
C10 C11 1.392(4) . ?
C10 C15 1.382(4) . ?
C10 C9 1.476(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(4) . ?
F2 C13 1.361(3) . ?
O2 H2A 0.8200 . ?
O2 C29 1.305(4) . ?
C27 H27 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.376(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.377(4) . ?
C13 C14 1.369(6) . ?
C13 C12 1.362(6) . ?
C1 H1 0.9300 . ?
C1 C6 1.367(4) . ?
C5 H5A 0.9300 . ?
C5 C6 1.369(5) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
N3 C34 1.299(4) . ?
N3 C35 1.445(5) . ?
N3 C33 1.433(7) . ?
O4 C34 1.243(5) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
O1 H1A 0.8200 . ?
O1 C31 1.454(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32 C31 1.475(7) . ?
C31 H31 0.9800 . ?
C31 C30 1.392(7) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C8 N1 C7 107.9(2) . . ?
C28 O7 H7 109.5 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 C29 118.9(3) . . ?
C19 C18 C29 121.1(3) . . ?
C22 O5 H5 109.5 . . ?
C18 C17 H17 120.2 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H17 120.2 . . ?
C8 N2 C16 128.6(2) . . ?
C8 N2 C9 106.6(2) . . ?
C9 N2 C16 123.70(19) . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 C22 118.8(3) . . ?
C19 C20 C22 121.4(3) . . ?
C17 C16 N2 118.8(2) . . ?
C21 C16 C17 120.6(3) . . ?
C21 C16 N2 120.5(3) . . ?
C24 C23 C28 118.7(2) . . ?
C24 C23 C8 123.2(2) . . ?
C28 C23 C8 118.0(2) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.3(2) . . ?
C25 C24 H24 120.4 . . ?
C20 C21 H21 119.9 . . ?
C16 C21 C20 120.2(3) . . ?
C16 C21 H21 119.9 . . ?
O7 C28 C23 122.5(2) . . ?
O7 C28 C27 117.6(2) . . ?
C27 C28 C23 120.0(3) . . ?
N1 C8 N2 110.9(2) . . ?
N1 C8 C23 122.5(2) . . ?
N2 C8 C23 126.7(3) . . ?
N1 C7 C3 120.4(2) . . ?
C9 C7 N1 108.1(3) . . ?
C9 C7 C3 131.3(2) . . ?
C2 C3 C7 119.8(2) . . ?
C4 C3 C7 123.3(3) . . ?
C4 C3 C2 116.8(3) . . ?
F3 C25 C24 118.5(2) . . ?
F3 C25 C26 118.7(2) . . ?
C24 C25 C26 122.7(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.2 . . ?
C25 C26 H26 120.7 . . ?
C27 C26 C25 118.6(3) . . ?
C27 C26 H26 120.7 . . ?
C3 C2 H2 119.0 . . ?
C1 C2 C3 121.9(3) . . ?
C1 C2 H2 119.0 . . ?
C11 C10 C9 121.2(3) . . ?
C15 C10 C11 119.5(3) . . ?
C15 C10 C9 119.3(3) . . ?
O5 C22 C20 112.6(3) . . ?
O6 C22 O5 125.0(3) . . ?
O6 C22 C20 122.3(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C29 O2 H2A 109.5 . . ?
C28 C27 H27 119.7 . . ?
C26 C27 C28 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
O3 C29 C18 122.9(3) . . ?
O3 C29 O2 122.8(3) . . ?
O2 C29 C18 114.2(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
N2 C9 C10 121.9(2) . . ?
C7 C9 N2 106.5(2) . . ?
C7 C9 C10 131.6(3) . . ?
F2 C13 C14 118.1(4) . . ?
F2 C13 C12 118.5(4) . . ?
C12 C13 C14 123.3(3) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 H1 120.7 . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5A 120.4 . . ?
C15 C14 H14 121.1 . . ?
C13 C14 C15 117.8(3) . . ?
C13 C14 H14 121.1 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
F1 C6 C1 119.4(3) . . ?
F1 C6 C5 118.6(3) . . ?
C1 C6 C5 122.0(3) . . ?
C34 N3 C35 121.4(4) . . ?
C34 N3 C33 122.2(4) . . ?
C33 N3 C35 116.1(3) . . ?
N3 C34 H34 117.8 . . ?
O4 C34 N3 124.5(4) . . ?
O4 C34 H34 117.8 . . ?
N3 C35 H35A 109.5 . . ?
N3 C35 H35B 109.5 . . ?
N3 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N3 C33 H33A 109.5 . . ?
N3 C33 H33B 109.5 . . ?
N3 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 O1 H1A 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
O1 C31 C32 111.5(4) . . ?
O1 C31 H31 103.0 . . ?
C32 C31 H31 103.0 . . ?
C30 C31 O1 113.7(5) . . ?
C30 C31 C32 119.9(5) . . ?
C30 C31 H31 103.0 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
N1 C7 C3 C2 10.6(4) . . . . ?
N1 C7 C3 C4 -167.0(2) . . . . ?
N1 C7 C9 N2 0.1(3) . . . . ?
N1 C7 C9 C10 -179.3(3) . . . . ?
O7 C28 C27 C26 -177.5(3) . . . . ?
C18 C17 C16 N2 175.1(2) . . . . ?
C18 C17 C16 C21 -0.9(4) . . . . ?
F3 C25 C26 C27 175.4(3) . . . . ?
C17 C18 C19 C20 0.9(4) . . . . ?
C17 C18 C29 O3 -10.7(5) . . . . ?
C17 C18 C29 O2 166.1(3) . . . . ?
C17 C16 C21 C20 0.4(4) . . . . ?
N2 C16 C21 C20 -175.6(2) . . . . ?
C16 N2 C8 N1 -167.6(2) . . . . ?
C16 N2 C8 C23 11.2(4) . . . . ?
C16 N2 C9 C7 168.5(2) . . . . ?
C16 N2 C9 C10 -12.0(4) . . . . ?
C23 C24 C25 F3 -177.6(3) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C23 C28 C27 C26 2.7(5) . . . . ?
C24 C23 C28 O7 175.3(3) . . . . ?
C24 C23 C28 C27 -4.9(4) . . . . ?
C24 C23 C8 N1 -150.1(3) . . . . ?
C24 C23 C8 N2 31.2(4) . . . . ?
C24 C25 C26 C27 -2.6(5) . . . . ?
C21 C20 C19 C18 -1.4(4) . . . . ?
C21 C20 C22 O5 -174.7(2) . . . . ?
C21 C20 C22 O6 5.1(4) . . . . ?
C28 C23 C24 C25 3.4(5) . . . . ?
C28 C23 C8 N1 25.3(4) . . . . ?
C28 C23 C8 N2 -153.4(3) . . . . ?
C8 N1 C7 C3 176.6(3) . . . . ?
C8 N1 C7 C9 0.2(3) . . . . ?
C8 N2 C16 C17 56.6(3) . . . . ?
C8 N2 C16 C21 -127.4(3) . . . . ?
C8 N2 C9 C7 -0.5(3) . . . . ?
C8 N2 C9 C10 179.1(2) . . . . ?
C8 C23 C24 C25 178.7(3) . . . . ?
C8 C23 C28 O7 -0.2(4) . . . . ?
C8 C23 C28 C27 179.6(3) . . . . ?
C7 N1 C8 N2 -0.5(3) . . . . ?
C7 N1 C8 C23 -179.4(2) . . . . ?
C7 C3 C2 C1 -176.7(3) . . . . ?
C7 C3 C4 C5 177.0(3) . . . . ?
C3 C7 C9 N2 -175.7(3) . . . . ?
C3 C7 C9 C10 4.9(5) . . . . ?
C3 C2 C1 C6 -0.7(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C25 C26 C27 C28 1.0(5) . . . . ?
C19 C18 C17 C16 0.3(4) . . . . ?
C19 C18 C29 O3 170.7(3) . . . . ?
C19 C18 C29 O2 -12.5(4) . . . . ?
C19 C20 C21 C16 0.8(4) . . . . ?
C19 C20 C22 O5 5.5(4) . . . . ?
C19 C20 C22 O6 -174.7(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C1 C6 F1 178.0(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C10 C15 C14 C13 -0.5(5) . . . . ?
C22 C20 C21 C16 -179.0(2) . . . . ?
C22 C20 C19 C18 178.4(3) . . . . ?
C11 C10 C15 C14 0.6(5) . . . . ?
C11 C10 C9 N2 67.5(4) . . . . ?
C11 C10 C9 C7 -113.1(4) . . . . ?
F2 C13 C14 C15 179.8(3) . . . . ?
F2 C13 C12 C11 -179.1(3) . . . . ?
C29 C18 C17 C16 -178.4(2) . . . . ?
C29 C18 C19 C20 179.5(3) . . . . ?
C4 C3 C2 C1 1.1(4) . . . . ?
C4 C5 C6 F1 -177.6(3) . . . . ?
C4 C5 C6 C1 0.7(5) . . . . ?
C15 C10 C11 C12 0.2(5) . . . . ?
C15 C10 C9 N2 -114.7(3) . . . . ?
C15 C10 C9 C7 64.7(4) . . . . ?
C9 N2 C16 C17 -109.8(3) . . . . ?
C9 N2 C16 C21 66.2(3) . . . . ?
C9 N2 C8 N1 0.6(3) . . . . ?
C9 N2 C8 C23 179.4(3) . . . . ?
C9 C7 C3 C2 -174.0(3) . . . . ?
C9 C7 C3 C4 8.4(5) . . . . ?
C9 C10 C11 C12 178.0(3) . . . . ?
C9 C10 C15 C14 -177.3(3) . . . . ?
C14 C13 C12 C11 1.1(6) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C35 N3 C34 O4 -1.5(6) . . . . ?
C33 N3 C34 O4 -174.9(4) . . . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1470807'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-06-26 downloaded from the CCDC.
;
_audit_creation_date             2015-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H17 F3 N2 O5'
_chemical_formula_sum            'C29 H17 F3 N2 O5'
_chemical_formula_weight         530.44
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.8457(2)
_cell_length_b                   20.0452(3)
_cell_length_c                   16.2309(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.7880(10)
_cell_angle_gamma                90
_cell_volume                     4670.08(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.5740
_cell_measurement_theta_min      3.5830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       laminar
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16557
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         24.683
_diffrn_reflns_theta_min         1.646
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6299
_reflns_number_total             7819
_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, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     716
_refine_ls_number_reflns         7819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1483
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C52(H52), C22(H22), C41(H41), C24(H24), C49(H49), C33(H33),
 C51(H51), C35(H35), C32(H32), C25(H25), C48(H48), C55(H55), C54(H54), C8(H8A),
 C12(H12), C11(H11), C6(H6), C9(H9), C3(H3), C5(H5A), C45(H45), C2(H2), C46(H46)
2.b Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4), O10(H10), O9(H9A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
F5 F 0.69912(11) 0.22338(8) 0.63486(12) 0.0667(5) Uani 1 1 d . . . . .
F4 F 0.29182(10) 0.22382(8) 0.76830(12) 0.0626(5) Uani 1 1 d . . . . .
F3 F 0.13840(10) 0.29571(8) 0.34868(10) 0.0542(4) Uani 1 1 d . . . . .
F1 F 0.65929(10) 0.77384(7) 0.99439(11) 0.0537(4) Uani 1 1 d . . . . .
F2 F 0.34995(10) 0.78515(7) 0.63034(11) 0.0550(4) Uani 1 1 d . . . . .
O7 O -0.02033(10) 0.57644(8) 0.37647(9) 0.0314(3) Uani 1 1 d . . . . .
O2 O 1.01328(10) 0.56931(9) 1.18335(9) 0.0369(4) Uani 1 1 d . . . . .
F6 F 0.91741(10) 0.26429(9) 0.95065(11) 0.0637(5) Uani 1 1 d . . . . .
O5 O 0.12745(10) 0.58750(8) 0.77855(8) 0.0331(4) Uani 1 1 d . . . . .
H5 H 0.0935 0.5912 0.8110 0.050 Uiso 1 1 calc GR . . . .
O8 O 0.11336(10) 0.56438(9) 0.33845(9) 0.0375(4) Uani 1 1 d . . . . .
O3 O 1.01304(9) 0.58902(8) 0.88058(9) 0.0341(4) Uani 1 1 d . . . . .
O4 O 0.87875(10) 0.57318(9) 0.78217(9) 0.0376(4) Uani 1 1 d . . . . .
H4 H 0.9114 0.5811 0.7495 0.056 Uiso 1 1 calc GR . . . .
O10 O 0.61308(10) 0.59510(8) 0.75404(10) 0.0374(4) Uani 1 1 d . . . . .
H10 H 0.5971 0.5583 0.7334 0.056 Uiso 1 1 calc GR . . . .
O1 O 0.87784(10) 0.56692(8) 1.21950(9) 0.0338(4) Uani 1 1 d . . . . .
O9 O 0.37831(10) 0.59909(8) 0.85736(10) 0.0371(4) Uani 1 1 d . . . . .
H9A H 0.3966 0.5603 0.8609 0.056 Uiso 1 1 calc GR . . . .
O6 O -0.00873(10) 0.58137(9) 0.68065(9) 0.0372(4) Uani 1 1 d . . . . .
N3 N 0.35900(11) 0.52091(9) 0.60555(10) 0.0270(4) Uani 1 1 d . . . . .
N1AA N 0.64254(11) 0.51091(8) 0.93928(10) 0.0239(4) Uani 1 1 d . . . . .
N10 N 0.49060(11) 0.50244(9) 0.88891(10) 0.0263(4) Uani 1 1 d . . . . .
N13 N 0.51016(11) 0.50747(9) 0.66029(11) 0.0298(4) Uani 1 1 d . . . . .
C36 C 0.73666(13) 0.53526(10) 0.96469(12) 0.0242(4) Uani 1 1 d . . . . .
C16 C 0.07668(14) 0.57444(10) 0.54945(13) 0.0255(4) Uani 1 1 d . . . . .
H16 H 0.0131 0.5831 0.5367 0.031 Uiso 1 1 calc R . . . .
C18 C 0.21368(14) 0.54821(11) 0.50366(13) 0.0265(4) Uani 1 1 d . . . . .
C53 C 0.34943(16) 0.27637(13) 0.79595(16) 0.0432(6) Uani 1 1 d . . . . .
C4 C 0.64424(17) 0.27816(13) 0.63164(17) 0.0465(6) Uani 1 1 d . . . . .
C20 C 0.06528(14) 0.56826(10) 0.39433(12) 0.0263(4) Uani 1 1 d . . . . .
C17 C 0.11990(13) 0.56369(10) 0.48472(12) 0.0242(4) Uani 1 1 d . . . . .
C39 C 0.92324(15) 0.57140(11) 1.01143(13) 0.0270(4) Uani 1 1 d . . . . .
C42 C 0.92724(14) 0.56574(11) 1.16424(12) 0.0271(5) Uani 1 1 d . . . . .
C15 C 0.12860(13) 0.57222(10) 0.63383(12) 0.0246(4) Uani 1 1 d . . . . .
C43 C 0.92958(14) 0.57692(11) 0.86110(13) 0.0285(5) Uani 1 1 d . . . . .
C52 C 0.31472(15) 0.34017(12) 0.78361(15) 0.0395(6) Uani 1 1 d . . . . .
H52 H 0.2523 0.3477 0.7567 0.047 Uiso 1 1 calc R . . . .
C44 C 0.69933(13) 0.39522(11) 0.92595(13) 0.0288(5) Uani 1 1 d . . . . .
C22 C 0.39121(15) 0.67199(12) 0.64033(14) 0.0356(5) Uani 1 1 d . . . . .
H22 H 0.3331 0.6615 0.6050 0.043 Uiso 1 1 calc R . . . .
C41 C 0.78177(14) 0.54136(10) 1.05033(12) 0.0260(4) Uani 1 1 d . . . . .
H41 H 0.7500 0.5331 1.0918 0.031 Uiso 1 1 calc R . . . .
C50 C 0.46779(14) 0.38293(11) 0.85377(12) 0.0291(5) Uani 1 1 d . . . . .
C24 C 0.49817(16) 0.75518(13) 0.71455(15) 0.0404(6) Uani 1 1 d . . . . .
H24 H 0.5111 0.7996 0.7293 0.048 Uiso 1 1 calc R . . . .
C49 C 0.74432(14) 0.36907(12) 1.00538(14) 0.0345(5) Uani 1 1 d . . . . .
H49 H 0.7252 0.3818 1.0534 0.041 Uiso 1 1 calc R . . . .
C33 C 0.50110(17) 0.75282(13) 0.92860(16) 0.0431(6) Uani 1 1 d . . . . .
H33 H 0.4884 0.7982 0.9291 0.052 Uiso 1 1 calc R . . . .
C51 C 0.37452(14) 0.39305(12) 0.81209(13) 0.0329(5) Uani 1 1 d . . . . .
H51 H 0.3518 0.4364 0.8032 0.039 Uiso 1 1 calc R . . . .
C56 C 0.62329(13) 0.44407(11) 0.91673(12) 0.0262(4) Uani 1 1 d . . . . .
C19 C 0.07631(14) 0.58129(10) 0.70027(12) 0.0265(4) Uani 1 1 d . . . . .
C26 C 0.54391(14) 0.63991(12) 0.72358(13) 0.0316(5) Uani 1 1 d . . . . .
C35 C 0.61226(15) 0.66283(11) 0.96149(14) 0.0328(5) Uani 1 1 d . . . . .
H35 H 0.6732 0.6488 0.9844 0.039 Uiso 1 1 calc R . . . .
C21 C 0.45620(14) 0.62123(11) 0.67125(13) 0.0296(5) Uani 1 1 d . . . . .
C23 C 0.41357(16) 0.73668(12) 0.66236(15) 0.0390(5) Uani 1 1 d . . . . .
C28 C 0.47437(14) 0.44819(11) 0.62410(13) 0.0306(5) Uani 1 1 d . . . . .
C58 C 0.55933(13) 0.54468(11) 0.91982(12) 0.0254(4) Uani 1 1 d . . . . .
C32 C 0.43130(16) 0.70775(12) 0.89492(15) 0.0395(6) Uani 1 1 d . . . . .
H32 H 0.3706 0.7229 0.8733 0.047 Uiso 1 1 calc R . . . .
C25 C 0.56305(16) 0.70640(12) 0.74438(14) 0.0388(5) Uani 1 1 d . . . . .
H25 H 0.6209 0.7181 0.7792 0.047 Uiso 1 1 calc R . . . .
C14 C 0.22343(14) 0.55764(11) 0.65403(13) 0.0268(4) Uani 1 1 d . . . . .
C29 C 0.38073(14) 0.45510(11) 0.58805(13) 0.0297(5) Uani 1 1 d . . . . .
C34 C 0.59013(16) 0.72919(12) 0.96154(15) 0.0387(5) Uani 1 1 d . . . . .
C57 C 0.52811(14) 0.44004(11) 0.88580(12) 0.0269(5) Uani 1 1 d . . . . .
C48 C 0.81740(15) 0.32429(12) 1.01363(15) 0.0395(6) Uani 1 1 d . . . . .
H48 H 0.8471 0.3064 1.0665 0.047 Uiso 1 1 calc R . . . .
C30 C 0.54221(14) 0.61615(11) 0.92663(12) 0.0274(5) Uani 1 1 d . . . . .
C55 C 0.50009(15) 0.31735(12) 0.86494(15) 0.0384(5) Uani 1 1 d . . . . .
H55 H 0.5623 0.3094 0.8922 0.046 Uiso 1 1 calc R . . . .
C27 C 0.44050(14) 0.55145(11) 0.64799(13) 0.0290(5) Uani 1 1 d . . . . .
C31 C 0.45028(14) 0.64002(11) 0.89277(13) 0.0310(5) Uani 1 1 d . . . . .
C54 C 0.44157(17) 0.26405(13) 0.83627(17) 0.0449(6) Uani 1 1 d . . . . .
H54 H 0.4639 0.2205 0.8440 0.054 Uiso 1 1 calc R . . . .
C7 C 0.31526(14) 0.41127(11) 0.52838(14) 0.0305(5) Uani 1 1 d . . . . .
C10 C 0.19729(15) 0.33368(12) 0.40824(15) 0.0382(5) Uani 1 1 d . . . . .
C40 C 0.87521(14) 0.55997(10) 1.07351(12) 0.0264(4) Uani 1 1 d . . . . .
C8 C 0.23616(15) 0.38351(13) 0.54517(15) 0.0395(6) Uani 1 1 d . . . . .
H8A H 0.2228 0.3916 0.5972 0.047 Uiso 1 1 calc R . . . .
C12 C 0.33326(15) 0.39892(12) 0.44957(15) 0.0375(5) Uani 1 1 d . . . . .
H12 H 0.3864 0.4170 0.4379 0.045 Uiso 1 1 calc R . . . .
C1 C 0.53312(14) 0.38877(12) 0.62661(14) 0.0331(5) Uani 1 1 d . . . . .
C11 C 0.27347(16) 0.36016(13) 0.38796(16) 0.0432(6) Uani 1 1 d . . . . .
H11 H 0.2850 0.3526 0.3351 0.052 Uiso 1 1 calc R . . . .
C6 C 0.62420(16) 0.39499(13) 0.62074(16) 0.0406(6) Uani 1 1 d . . . . .
H6 H 0.6481 0.4372 0.6154 0.049 Uiso 1 1 calc R . . . .
C47 C 0.84445(15) 0.30722(13) 0.94251(17) 0.0436(6) Uani 1 1 d . . . . .
C9 C 0.17699(16) 0.34390(13) 0.48496(16) 0.0433(6) Uani 1 1 d . . . . .
H9 H 0.1245 0.3246 0.4964 0.052 Uiso 1 1 calc R . . . .
C3 C 0.55518(18) 0.26974(14) 0.6403(2) 0.0586(8) Uani 1 1 d . . . . .
H3 H 0.5326 0.2275 0.6478 0.070 Uiso 1 1 calc R . . . .
C5 C 0.68017(17) 0.33958(14) 0.62275(17) 0.0473(6) Uani 1 1 d . . . . .
H5A H 0.7410 0.3441 0.6181 0.057 Uiso 1 1 calc R . . . .
C45 C 0.72786(16) 0.37513(13) 0.85498(15) 0.0418(6) Uani 1 1 d . . . . .
H45 H 0.6975 0.3916 0.8015 0.050 Uiso 1 1 calc R . . . .
C2 C 0.49988(16) 0.32576(13) 0.63762(19) 0.0496(7) Uani 1 1 d . . . . .
H2 H 0.4394 0.3210 0.6433 0.060 Uiso 1 1 calc R . . . .
C46 C 0.80108(18) 0.33089(14) 0.86269(17) 0.0517(7) Uani 1 1 d . . . . .
H46 H 0.8205 0.3175 0.8151 0.062 Uiso 1 1 calc R . . . .
H1 H 0.917(3) 0.5729(19) 1.278(3) 0.097(12) Uiso 1 1 d . . . . .
H8 H 0.073(3) 0.567(2) 0.282(3) 0.139(17) Uiso 1 1 d . . . . .
C0AA C 0.87679(14) 0.56557(10) 0.92617(12) 0.0263(4) Uiso 1 1 d . . . . .
C1AA C 0.78339(14) 0.54754(10) 0.90227(12) 0.0253(4) Uiso 1 1 d . . . . .
H1AA H 0.7502(15) 0.5413(11) 0.8400(15) 0.034(6) Uiso 1 1 d . . . . .
H39 H 0.9864(16) 0.5834(11) 1.0290(13) 0.026(6) Uiso 1 1 d . . . . .
C2AA C 0.26473(14) 0.54450(10) 0.58790(12) 0.0261(4) Uiso 1 1 d . . . . .
H18 H 0.2430(17) 0.5384(12) 0.4594(16) 0.039(6) Uiso 1 1 d . . . . .
H14 H 0.2564(14) 0.5541(10) 0.7113(14) 0.022(5) Uiso 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
F5 C4 1.360(3) . ?
F4 C53 1.359(3) . ?
F3 C10 1.359(3) . ?
F1 C34 1.364(3) . ?
F2 C23 1.362(3) . ?
O7 C20 1.240(2) . ?
O2 C42 1.237(3) . ?
F6 C47 1.363(3) . ?
O5 C19 1.309(2) . ?
O8 C20 1.292(2) . ?
O3 C43 1.222(2) . ?
O4 C43 1.312(2) . ?
O10 C26 1.359(3) . ?
O1 C42 1.296(2) . ?
O9 C31 1.353(3) . ?
O6 C19 1.221(2) . ?
N3 C29 1.404(3) . ?
N3 C27 1.374(3) . ?
N3 C2AA 1.435(3) . ?
N1AA C36 1.438(2) . ?
N1AA C56 1.399(3) . ?
N1AA C58 1.373(2) . ?
N10 C58 1.322(3) . ?
N10 C57 1.375(3) . ?
N13 C28 1.371(3) . ?
N13 C27 1.335(3) . ?
C36 C41 1.386(3) . ?
C36 C1AA 1.388(3) . ?
C16 C17 1.381(3) . ?
C16 C15 1.390(3) . ?
C18 C17 1.382(3) . ?
C18 C2AA 1.386(3) . ?
C53 C52 1.374(3) . ?
C53 C54 1.380(3) . ?
C4 C3 1.375(4) . ?
C4 C5 1.364(4) . ?
C20 C17 1.487(3) . ?
C39 C40 1.394(3) . ?
C39 C0AA 1.385(3) . ?
C42 C40 1.483(3) . ?
C15 C19 1.492(3) . ?
C15 C14 1.393(3) . ?
C43 C0AA 1.485(3) . ?
C52 C51 1.384(3) . ?
C44 C49 1.394(3) . ?
C44 C56 1.473(3) . ?
C44 C45 1.385(3) . ?
C22 C21 1.404(3) . ?
C22 C23 1.363(3) . ?
C41 C40 1.392(3) . ?
C50 C51 1.392(3) . ?
C50 C57 1.465(3) . ?
C50 C55 1.395(3) . ?
C24 C23 1.374(3) . ?
C24 C25 1.371(3) . ?
C49 C48 1.388(3) . ?
C33 C32 1.378(3) . ?
C33 C34 1.377(3) . ?
C56 C57 1.376(3) . ?
C26 C21 1.412(3) . ?
C26 C25 1.386(3) . ?
C35 C34 1.370(3) . ?
C35 C30 1.406(3) . ?
C21 C27 1.452(3) . ?
C28 C29 1.371(3) . ?
C28 C1 1.471(3) . ?
C58 C30 1.464(3) . ?
C32 C31 1.389(3) . ?
C14 C2AA 1.391(3) . ?
C29 C7 1.475(3) . ?
C48 C47 1.359(4) . ?
C30 C31 1.418(3) . ?
C55 C54 1.381(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.394(3) . ?
C10 C11 1.363(3) . ?
C10 C9 1.369(4) . ?
C8 C9 1.385(3) . ?
C12 C11 1.392(3) . ?
C1 C6 1.385(3) . ?
C1 C2 1.384(3) . ?
C6 C5 1.382(3) . ?
C47 C46 1.376(4) . ?
C3 C2 1.385(4) . ?
C45 C46 1.384(3) . ?
C0AA C1AA 1.389(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C29 N3 C2AA 122.13(17) . . ?
C27 N3 C29 107.55(16) . . ?
C27 N3 C2AA 129.98(18) . . ?
C56 N1AA C36 121.26(16) . . ?
C58 N1AA C36 130.56(17) . . ?
C58 N1AA C56 107.48(16) . . ?
C58 N10 C57 108.42(16) . . ?
C27 N13 C28 107.92(17) . . ?
C41 C36 N1AA 120.21(17) . . ?
C41 C36 C1AA 120.85(18) . . ?
C1AA C36 N1AA 118.75(16) . . ?
C17 C16 C15 119.75(18) . . ?
C17 C18 C2AA 119.85(18) . . ?
F4 C53 C52 119.5(2) . . ?
F4 C53 C54 118.8(2) . . ?
C52 C53 C54 121.7(2) . . ?
F5 C4 C3 118.6(2) . . ?
F5 C4 C5 119.1(2) . . ?
C5 C4 C3 122.3(2) . . ?
O7 C20 O8 124.11(18) . . ?
O7 C20 C17 120.47(17) . . ?
O8 C20 C17 115.41(17) . . ?
C16 C17 C18 120.21(18) . . ?
C16 C17 C20 119.93(17) . . ?
C18 C17 C20 119.86(17) . . ?
C0AA C39 C40 119.49(19) . . ?
O2 C42 O1 123.78(18) . . ?
O2 C42 C40 119.75(18) . . ?
O1 C42 C40 116.47(18) . . ?
C16 C15 C19 116.63(17) . . ?
C16 C15 C14 120.77(18) . . ?
C14 C15 C19 122.46(17) . . ?
O3 C43 O4 123.79(18) . . ?
O3 C43 C0AA 122.05(18) . . ?
O4 C43 C0AA 114.16(17) . . ?
C53 C52 C51 118.6(2) . . ?
C49 C44 C56 121.18(19) . . ?
C45 C44 C49 118.9(2) . . ?
C45 C44 C56 119.88(19) . . ?
C23 C22 C21 119.8(2) . . ?
C36 C41 C40 119.19(18) . . ?
C51 C50 C57 120.1(2) . . ?
C51 C50 C55 117.8(2) . . ?
C55 C50 C57 122.11(19) . . ?
C25 C24 C23 118.3(2) . . ?
C48 C49 C44 120.7(2) . . ?
C34 C33 C32 118.6(2) . . ?
C52 C51 C50 121.6(2) . . ?
N1AA C56 C44 120.67(17) . . ?
C57 C56 N1AA 105.90(18) . . ?
C57 C56 C44 133.4(2) . . ?
O5 C19 C15 115.68(17) . . ?
O6 C19 O5 123.91(18) . . ?
O6 C19 C15 120.39(17) . . ?
O10 C26 C21 122.6(2) . . ?
O10 C26 C25 117.26(19) . . ?
C25 C26 C21 120.1(2) . . ?
C34 C35 C30 119.6(2) . . ?
C22 C21 C26 117.8(2) . . ?
C22 C21 C27 123.73(19) . . ?
C26 C21 C27 118.31(19) . . ?
F2 C23 C22 118.7(2) . . ?
F2 C23 C24 118.6(2) . . ?
C22 C23 C24 122.8(2) . . ?
N13 C28 C1 121.86(18) . . ?
C29 C28 N13 109.59(19) . . ?
C29 C28 C1 128.6(2) . . ?
N1AA C58 C30 128.93(18) . . ?
N10 C58 N1AA 109.47(18) . . ?
N10 C58 C30 121.55(17) . . ?
C33 C32 C31 120.9(2) . . ?
C24 C25 C26 121.2(2) . . ?
C2AA C14 C15 118.46(18) . . ?
N3 C29 C7 123.07(17) . . ?
C28 C29 N3 105.60(19) . . ?
C28 C29 C7 130.3(2) . . ?
F1 C34 C33 118.6(2) . . ?
F1 C34 C35 118.7(2) . . ?
C35 C34 C33 122.7(2) . . ?
N10 C57 C50 120.48(18) . . ?
N10 C57 C56 108.71(19) . . ?
C56 C57 C50 130.8(2) . . ?
C47 C48 C49 118.3(2) . . ?
C35 C30 C58 123.84(18) . . ?
C35 C30 C31 118.1(2) . . ?
C31 C30 C58 117.99(19) . . ?
C54 C55 C50 121.3(2) . . ?
N3 C27 C21 128.46(19) . . ?
N13 C27 N3 109.29(19) . . ?
N13 C27 C21 122.04(18) . . ?
O9 C31 C32 117.39(19) . . ?
O9 C31 C30 122.5(2) . . ?
C32 C31 C30 120.1(2) . . ?
C53 C54 C55 118.9(2) . . ?
C8 C7 C29 124.0(2) . . ?
C8 C7 C12 118.6(2) . . ?
C12 C7 C29 117.38(19) . . ?
F3 C10 C11 118.0(2) . . ?
F3 C10 C9 118.7(2) . . ?
C11 C10 C9 123.4(2) . . ?
C39 C40 C42 118.18(18) . . ?
C41 C40 C39 120.46(18) . . ?
C41 C40 C42 121.32(18) . . ?
C9 C8 C7 120.5(2) . . ?
C11 C12 C7 121.4(2) . . ?
C6 C1 C28 120.5(2) . . ?
C2 C1 C28 120.9(2) . . ?
C2 C1 C6 118.5(2) . . ?
C10 C11 C12 117.4(2) . . ?
C5 C6 C1 121.2(2) . . ?
F6 C47 C46 118.6(2) . . ?
C48 C47 F6 118.4(2) . . ?
C48 C47 C46 123.0(2) . . ?
C10 C9 C8 118.7(2) . . ?
C4 C3 C2 118.4(3) . . ?
C4 C5 C6 118.6(2) . . ?
C46 C45 C44 120.7(2) . . ?
C1 C2 C3 121.1(2) . . ?
C47 C46 C45 118.3(2) . . ?
C39 C0AA C43 118.64(18) . . ?
C39 C0AA C1AA 120.55(19) . . ?
C1AA C0AA C43 120.78(18) . . ?
C36 C1AA C0AA 119.44(18) . . ?
C18 C2AA N3 118.33(17) . . ?
C18 C2AA C14 120.90(18) . . ?
C14 C2AA N3 120.53(17) . . ?

_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 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 1470813'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-06-26 downloaded from the CCDC.
;
_audit_creation_date             2016-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H17 F3 N2 O'
_chemical_formula_sum            'C27 H17 F3 N2 O'
_chemical_formula_weight         442.42
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.1247(5)
_cell_length_b                   10.5410(4)
_cell_length_c                   14.3333(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.617(3)
_cell_angle_gamma                90
_cell_volume                     2129.81(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4794
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.8170
_cell_measurement_theta_min      3.4430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13336
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.968
_diffrn_reflns_theta_min         2.848
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3207
_reflns_number_total             5156
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.046
_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1789
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C21(H21), C17(H17), C25(H25), C3(H3), C23(H23), C18(H18), C5(H5),
 C20(H20), C26(H26), C1(H1), C2(H2), C6(H6), C11(H11), C14(H14), C13(H13)
2.b Idealised tetrahedral OH refined as rotating group:
 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
N2 N 0.08000(11) 0.88471(15) 0.08347(10) 0.0417(4) Uani 1 1 d . . . . .
N1 N 0.15815(10) 0.92913(14) -0.04153(9) 0.0388(4) Uani 1 1 d . . . . .
C16 C 0.16074(12) 1.02313(18) 0.20412(11) 0.0396(4) Uani 1 1 d . . . . .
C15 C 0.28504(12) 1.07785(17) 0.02219(11) 0.0376(4) Uani 1 1 d . . . . .
C9 C 0.08784(12) 0.85749(17) -0.00680(12) 0.0396(4) Uani 1 1 d . . . . .
C7 C 0.19789(12) 1.00316(16) 0.03144(11) 0.0377(4) Uani 1 1 d . . . . .
C8 C 0.14776(12) 0.97494(17) 0.10787(11) 0.0382(4) Uani 1 1 d . . . . .
C22 C 0.03001(12) 0.75890(18) -0.05505(12) 0.0415(4) Uani 1 1 d . . . . .
C10 C 0.29202(14) 1.17405(19) -0.04332(12) 0.0466(5) Uani 1 1 d . . . . .
H10 H 0.2392 1.1962 -0.0819 0.056 Uiso 1 1 calc R . . . .
C21 C 0.13860(15) 0.9475(2) 0.27896(13) 0.0528(5) Uani 1 1 d . . . . .
H21 H 0.1119 0.8678 0.2677 0.063 Uiso 1 1 calc R . . . .
C4 C 0.18921(13) 0.93710(18) -0.13568(11) 0.0426(4) Uani 1 1 d . . . . .
C27 C -0.03929(14) 0.69572(19) -0.00662(13) 0.0487(5) Uani 1 1 d . . . . .
C17 C 0.19721(15) 1.14303(19) 0.22349(12) 0.0485(5) Uani 1 1 d . . . . .
H17 H 0.2101 1.1968 0.1744 0.058 Uiso 1 1 calc R . . . .
C25 C -0.07895(16) 0.5637(2) -0.13980(16) 0.0634(6) Uani 1 1 d . . . . .
H25 H -0.1149 0.4991 -0.1686 0.076 Uiso 1 1 calc R . . . .
C3 C 0.27275(15) 0.8800(2) -0.15651(14) 0.0563(5) Uani 1 1 d . . . . .
H3 H 0.3069 0.8315 -0.1118 0.068 Uiso 1 1 calc R . . . .
C23 C 0.04309(15) 0.7199(2) -0.14644(14) 0.0562(5) Uani 1 1 d . . . . .
H23 H 0.0889 0.7588 -0.1804 0.067 Uiso 1 1 calc R . . . .
C19 C 0.19483(15) 1.1052(2) 0.38576(13) 0.0531(5) Uani 1 1 d . . . . .
C18 C 0.21488(16) 1.1842(2) 0.31510(14) 0.0570(5) Uani 1 1 d . . . . .
H18 H 0.2400 1.2645 0.3276 0.068 Uiso 1 1 calc R . . . .
C24 C -0.01110(16) 0.6252(2) -0.18571(15) 0.0590(6) Uani 1 1 d . . . . .
C5 C 0.13700(18) 1.0068(2) -0.20183(14) 0.0604(6) Uani 1 1 d . . . . .
H5 H 0.0796 1.0429 -0.1876 0.072 Uiso 1 1 calc R . . . .
C20 C 0.15572(17) 0.9892(2) 0.37046(13) 0.0626(6) Uani 1 1 d . . . . .
H20 H 0.1406 0.9383 0.4204 0.075 Uiso 1 1 calc R . . . .
C26 C -0.09265(16) 0.5997(2) -0.05000(16) 0.0638(6) Uani 1 1 d . . . . .
H26 H -0.1387 0.5590 -0.0174 0.077 Uiso 1 1 calc R . . . .
C1 C 0.2546(2) 0.9677(3) -0.30956(17) 0.0844(9) Uani 1 1 d . . . . .
H1 H 0.2777 0.9792 -0.3683 0.101 Uiso 1 1 calc R . . . .
C12 C 0.45193(15) 1.2063(2) 0.00812(17) 0.0643(6) Uani 1 1 d . . . . .
C2 C 0.30501(19) 0.8954(3) -0.24379(17) 0.0792(8) Uani 1 1 d . . . . .
H2 H 0.3613 0.8569 -0.2587 0.095 Uiso 1 1 calc R . . . .
C6 C 0.1704(2) 1.0228(3) -0.28908(14) 0.0793(8) Uani 1 1 d . . . . .
H6 H 0.1361 1.0707 -0.3340 0.095 Uiso 1 1 calc R . . . .
F2 F 0.21622(10) 1.14306(16) 0.47559(8) 0.0803(5) Uani 1 1 d . . . . .
O1 O -0.05655(12) 0.72375(17) 0.08343(10) 0.0702(5) Uani 1 1 d . . . . .
H1A H -0.0180 0.7766 0.1040 0.105 Uiso 1 1 calc GR . . . .
F3 F 0.00387(11) 0.59059(18) -0.27514(10) 0.0958(6) Uani 1 1 d . . . . .
F1 F 0.53481(11) 1.26994(19) 0.00107(14) 0.1145(7) Uani 1 1 d . . . . .
C11 C 0.37685(15) 1.2371(2) -0.05159(14) 0.0563(5) Uani 1 1 d . . . . .
H11 H 0.3824 1.2992 -0.0970 0.068 Uiso 1 1 calc R . . . .
C14 C 0.36422(14) 1.0489(2) 0.07954(14) 0.0544(5) Uani 1 1 d . . . . .
H14 H 0.3609 0.9839 0.1231 0.065 Uiso 1 1 calc R . . . .
C13 C 0.44803(16) 1.1141(3) 0.07359(18) 0.0716(7) Uani 1 1 d . . . . .
H13 H 0.5006 1.0954 0.1135 0.086 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
N2 C9 1.337(2) . ?
N2 C8 1.379(2) . ?
N1 C9 1.366(2) . ?
N1 C7 1.394(2) . ?
N1 C4 1.447(2) . ?
C16 C8 1.471(2) . ?
C16 C21 1.388(3) . ?
C16 C17 1.386(3) . ?
C15 C7 1.474(2) . ?
C15 C10 1.390(3) . ?
C15 C14 1.380(3) . ?
C9 C22 1.468(3) . ?
C7 C8 1.374(2) . ?
C22 C27 1.403(3) . ?
C22 C23 1.396(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(3) . ?
C4 C3 1.374(3) . ?
C4 C5 1.377(3) . ?
C27 C26 1.385(3) . ?
C27 O1 1.361(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.361(3) . ?
C25 C26 1.368(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.368(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.358(3) . ?
C19 C18 1.355(3) . ?
C19 C20 1.354(3) . ?
C19 F2 1.364(2) . ?
C18 H18 0.9300 . ?
C24 F3 1.362(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(3) . ?
C20 H20 0.9300 . ?
C26 H26 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.375(4) . ?
C1 C6 1.371(4) . ?
C12 F1 1.358(2) . ?
C12 C11 1.359(3) . ?
C12 C13 1.355(3) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
O1 H1A 0.8200 . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.376(3) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N2 C8 107.16(14) . . ?
C9 N1 C7 107.67(13) . . ?
C9 N1 C4 129.92(14) . . ?
C7 N1 C4 122.38(14) . . ?
C21 C16 C8 120.37(18) . . ?
C17 C16 C8 121.70(16) . . ?
C17 C16 C21 117.91(17) . . ?
C10 C15 C7 123.07(16) . . ?
C14 C15 C7 118.58(16) . . ?
C14 C15 C10 118.33(17) . . ?
N2 C9 N1 109.91(15) . . ?
N2 C9 C22 122.04(15) . . ?
N1 C9 C22 127.98(15) . . ?
N1 C7 C15 122.04(14) . . ?
C8 C7 N1 105.88(15) . . ?
C8 C7 C15 131.49(15) . . ?
N2 C8 C16 121.31(15) . . ?
C7 C8 N2 109.36(15) . . ?
C7 C8 C16 129.28(16) . . ?
C27 C22 C9 119.20(15) . . ?
C23 C22 C9 123.22(16) . . ?
C23 C22 C27 117.52(17) . . ?
C15 C10 H10 119.7 . . ?
C11 C10 C15 120.52(18) . . ?
C11 C10 H10 119.7 . . ?
C16 C21 H21 119.6 . . ?
C16 C21 C20 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C3 C4 N1 119.47(17) . . ?
C3 C4 C5 120.95(18) . . ?
C5 C4 N1 119.50(17) . . ?
C26 C27 C22 120.09(18) . . ?
O1 C27 C22 122.57(17) . . ?
O1 C27 C26 117.34(17) . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.07(18) . . ?
C18 C17 H17 119.5 . . ?
C24 C25 H25 121.0 . . ?
C24 C25 C26 117.92(19) . . ?
C26 C25 H25 121.0 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.4 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.04(19) . . ?
C24 C23 H23 120.0 . . ?
C18 C19 F2 118.8(2) . . ?
C20 C19 C18 122.47(18) . . ?
C20 C19 F2 118.8(2) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.7(2) . . ?
C19 C18 H18 120.7 . . ?
C25 C24 F3 118.89(18) . . ?
C23 C24 C25 123.07(19) . . ?
C23 C24 F3 118.04(19) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C21 C20 H20 120.5 . . ?
C19 C20 C21 118.91(19) . . ?
C19 C20 H20 120.5 . . ?
C27 C26 H26 119.3 . . ?
C25 C26 C27 121.3(2) . . ?
C25 C26 H26 119.3 . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(2) . . ?
F1 C12 C11 118.5(2) . . ?
C13 C12 F1 118.6(2) . . ?
C13 C12 C11 122.9(2) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C5 C6 H6 120.2 . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 H6 120.2 . . ?
C27 O1 H1A 109.5 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.52(18) . . ?
C12 C11 H11 120.7 . . ?
C15 C14 H14 119.3 . . ?
C13 C14 C15 121.37(19) . . ?
C13 C14 H14 119.3 . . ?
C12 C13 C14 118.3(2) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?

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
N2 C9 C22 C27 3.5(3) . . . . ?
N2 C9 C22 C23 -173.51(19) . . . . ?
N1 C9 C22 C27 -179.97(18) . . . . ?
N1 C9 C22 C23 3.0(3) . . . . ?
N1 C7 C8 N2 0.9(2) . . . . ?
N1 C7 C8 C16 178.44(17) . . . . ?
N1 C4 C3 C2 -175.44(19) . . . . ?
N1 C4 C5 C6 174.84(19) . . . . ?
C16 C21 C20 C19 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C15 C7 C8 N2 -170.14(18) . . . . ?
C15 C7 C8 C16 7.4(3) . . . . ?
C15 C10 C11 C12 -2.5(3) . . . . ?
C15 C14 C13 C12 -1.5(4) . . . . ?
C9 N2 C8 C16 -177.86(16) . . . . ?
C9 N2 C8 C7 -0.1(2) . . . . ?
C9 N1 C7 C15 170.73(16) . . . . ?
C9 N1 C7 C8 -1.37(19) . . . . ?
C9 N1 C4 C3 -105.2(2) . . . . ?
C9 N1 C4 C5 77.9(2) . . . . ?
C9 C22 C27 C26 -178.0(2) . . . . ?
C9 C22 C27 O1 1.2(3) . . . . ?
C9 C22 C23 C24 177.9(2) . . . . ?
C7 N1 C9 N2 1.36(19) . . . . ?
C7 N1 C9 C22 -175.51(18) . . . . ?
C7 N1 C4 C3 76.9(2) . . . . ?
C7 N1 C4 C5 -99.9(2) . . . . ?
C7 C15 C10 C11 -177.09(17) . . . . ?
C7 C15 C14 C13 179.2(2) . . . . ?
C8 N2 C9 N1 -0.8(2) . . . . ?
C8 N2 C9 C22 176.31(16) . . . . ?
C8 C16 C21 C20 176.23(19) . . . . ?
C8 C16 C17 C18 -175.77(18) . . . . ?
C22 C27 C26 C25 0.5(4) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C22 C23 C24 F3 179.8(2) . . . . ?
C10 C15 C7 N1 60.9(2) . . . . ?
C10 C15 C7 C8 -129.3(2) . . . . ?
C10 C15 C14 C13 0.9(3) . . . . ?
C21 C16 C8 N2 28.2(3) . . . . ?
C21 C16 C8 C7 -149.1(2) . . . . ?
C21 C16 C17 C18 2.7(3) . . . . ?
C4 N1 C9 N2 -176.71(17) . . . . ?
C4 N1 C9 C22 6.4(3) . . . . ?
C4 N1 C7 C15 -11.0(3) . . . . ?
C4 N1 C7 C8 176.88(15) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C27 C22 C23 C24 0.8(3) . . . . ?
C17 C16 C8 N2 -153.40(18) . . . . ?
C17 C16 C8 C7 29.3(3) . . . . ?
C17 C16 C21 C20 -2.3(3) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C23 C22 C27 C26 -0.9(3) . . . . ?
C23 C22 C27 O1 178.4(2) . . . . ?
C18 C19 C20 C21 2.4(3) . . . . ?
C24 C25 C26 C27 -0.1(4) . . . . ?
C5 C4 C3 C2 1.4(3) . . . . ?
C20 C19 C18 C17 -2.0(3) . . . . ?
C26 C25 C24 C23 0.1(4) . . . . ?
C26 C25 C24 F3 179.8(2) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C6 C1 C2 C3 -1.4(4) . . . . ?
F2 C19 C18 C17 176.97(18) . . . . ?
F2 C19 C20 C21 -176.54(19) . . . . ?
O1 C27 C26 C25 -178.8(2) . . . . ?
F1 C12 C11 C10 -178.8(2) . . . . ?
F1 C12 C13 C14 -179.1(2) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C14 C15 C7 N1 -117.4(2) . . . . ?
C14 C15 C7 C8 52.5(3) . . . . ?
C14 C15 C10 C11 1.2(3) . . . . ?
C13 C12 C11 C10 1.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
