# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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 1574457'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H33 F N2 O5'
_chemical_formula_weight         532.59

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.601(8)
_cell_length_b                   10.967(4)
_cell_length_c                   11.290(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.377(11)
_cell_angle_gamma                90.00
_cell_volume                     2796.0(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1100
_cell_measurement_theta_min      2.589
_cell_measurement_theta_max      19.201

_exptl_crystal_description       Strip
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15356
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_sigmaI/netI    0.1150
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         0.90
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4936
_reflns_number_gt                2162
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2009)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0820P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4936
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.2103
_refine_ls_wR_factor_gt          0.1539
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.05678(14) -0.0281(2) 0.5612(3) 0.0973(12) Uani 1 1 d . . .
N1 N 0.30345(13) 0.8539(3) 0.3670(3) 0.0396(9) Uani 1 1 d . . .
N2 N 0.18618(13) 0.7511(3) 0.3589(3) 0.0361(8) Uani 1 1 d . . .
H2A H 0.1906 0.6802 0.3215 0.043 Uiso 1 1 d R . .
O1 O 0.06238(18) 0.5281(3) 0.6638(4) 0.0889(12) Uani 1 1 d . . .
O2 O 0.22695(16) 0.4716(3) 0.3231(3) 0.0665(10) Uani 1 1 d . . .
O3 O 0.19200(15) 0.5836(2) 0.1834(3) 0.0614(10) Uani 1 1 d . . .
O4 O 0.21649(15) 0.0652(2) 0.1012(3) 0.0613(10) Uani 1 1 d . . .
O5 O 0.24345(14) 0.2044(3) -0.0347(3) 0.0598(9) Uani 1 1 d . . .
H5 H 0.2428 0.1455 -0.0787 0.090 Uiso 1 1 d R . .
C1 C 0.4091(2) 0.9743(6) 0.1637(5) 0.0781(17) Uani 1 1 d . . .
H1 H 0.4228 0.8991 0.1386 0.094 Uiso 1 1 calc R . .
C2 C 0.4173(3) 1.0764(8) 0.0947(6) 0.107(2) Uani 1 1 d . . .
H2 H 0.4354 1.0695 0.0225 0.129 Uiso 1 1 calc R . .
C3 C 0.3986(3) 1.1876(8) 0.1328(9) 0.117(3) Uani 1 1 d . . .
H3 H 0.4048 1.2568 0.0873 0.140 Uiso 1 1 calc R . .
C4 C 0.3700(3) 1.1976(6) 0.2408(8) 0.098(2) Uani 1 1 d . . .
H4 H 0.3566 1.2733 0.2652 0.118 Uiso 1 1 calc R . .
C5 C 0.3617(2) 1.0974(4) 0.3101(5) 0.0687(16) Uani 1 1 d . . .
H5A H 0.3439 1.1057 0.3825 0.082 Uiso 1 1 calc R . .
C6 C 0.37989(18) 0.9830(4) 0.2729(5) 0.0521(13) Uani 1 1 d . . .
C7 C 0.36792(18) 0.8706(4) 0.3477(4) 0.0488(12) Uani 1 1 d . . .
H7 H 0.3830 0.7982 0.3080 0.059 Uiso 1 1 calc R . .
C8 C 0.39716(18) 0.8814(4) 0.4657(4) 0.0476(12) Uani 1 1 d . . .
C9 C 0.4543(2) 0.8423(5) 0.4761(5) 0.0730(16) Uani 1 1 d . . .
H9 H 0.4728 0.8074 0.4122 0.088 Uiso 1 1 calc R . .
C10 C 0.4828(3) 0.8555(6) 0.5799(7) 0.098(2) Uani 1 1 d . . .
H10A H 0.5216 0.8283 0.5895 0.117 Uiso 1 1 calc R . .
C11 C 0.4558(3) 0.9088(6) 0.6744(6) 0.092(2) Uani 1 1 d . . .
H11 H 0.4773 0.9179 0.7459 0.110 Uiso 1 1 calc R . .
C12 C 0.3985(3) 0.9486(4) 0.6665(5) 0.0772(17) Uani 1 1 d . . .
H12 H 0.3808 0.9840 0.7310 0.093 Uiso 1 1 calc R . .
C13 C 0.3688(2) 0.9347(4) 0.5624(4) 0.0604(14) Uani 1 1 d . . .
H13 H 0.3296 0.9601 0.5536 0.073 Uiso 1 1 calc R . .
C14 C 0.28924(17) 0.7375(4) 0.4247(4) 0.0439(11) Uani 1 1 d . . .
H14A H 0.3154 0.7264 0.4942 0.053 Uiso 1 1 calc R . .
H14B H 0.2961 0.6709 0.3705 0.053 Uiso 1 1 calc R . .
C15 C 0.22388(17) 0.7333(4) 0.4622(3) 0.0391(11) Uani 1 1 d . . .
H15A H 0.2156 0.6551 0.4981 0.047 Uiso 1 1 calc R . .
H15B H 0.2170 0.7968 0.5199 0.047 Uiso 1 1 calc R . .
C16 C 0.20618(17) 0.8591(4) 0.2887(4) 0.0432(11) Uani 1 1 d . . .
H16A H 0.1992 0.9327 0.3337 0.052 Uiso 1 1 calc R . .
H16B H 0.1821 0.8638 0.2157 0.052 Uiso 1 1 calc R . .
C17 C 0.27122(17) 0.8553(4) 0.2581(4) 0.0479(12) Uani 1 1 d . . .
H17A H 0.2795 0.7828 0.2124 0.057 Uiso 1 1 calc R . .
H17B H 0.2814 0.9265 0.2122 0.057 Uiso 1 1 calc R . .
C18 C 0.12096(18) 0.7643(4) 0.3900(4) 0.0537(13) Uani 1 1 d . . .
H18A H 0.0970 0.7478 0.3185 0.064 Uiso 1 1 calc R . .
H18B H 0.1145 0.8491 0.4104 0.064 Uiso 1 1 calc R . .
C19 C 0.09651(19) 0.6856(4) 0.4901(4) 0.0508(12) Uani 1 1 d . . .
H19A H 0.1196 0.7019 0.5628 0.061 Uiso 1 1 calc R . .
H19B H 0.0560 0.7102 0.5027 0.061 Uiso 1 1 calc R . .
C20 C 0.09749(19) 0.5505(4) 0.4665(4) 0.0490(12) Uani 1 1 d . . .
H20A H 0.1376 0.5253 0.4513 0.059 Uiso 1 1 calc R . .
H20B H 0.0727 0.5325 0.3965 0.059 Uiso 1 1 calc R . .
C21 C 0.07519(19) 0.4790(4) 0.5719(4) 0.0493(12) Uani 1 1 d . . .
C22 C 0.07104(17) 0.3447(4) 0.5640(4) 0.0439(11) Uani 1 1 d . . .
C23 C 0.0450(2) 0.2823(4) 0.6605(4) 0.0599(13) Uani 1 1 d . . .
H23 H 0.0313 0.3259 0.7245 0.072 Uiso 1 1 calc R . .
C24 C 0.0403(2) 0.1542(5) 0.6576(5) 0.0661(15) Uani 1 1 d . . .
H24 H 0.0234 0.1117 0.7189 0.079 Uiso 1 1 calc R . .
C25 C 0.0614(2) 0.0942(4) 0.5618(6) 0.0638(15) Uani 1 1 d . . .
C26 C 0.0868(2) 0.1517(5) 0.4660(5) 0.0654(15) Uani 1 1 d . . .
H26 H 0.0999 0.1064 0.4026 0.079 Uiso 1 1 calc R . .
C27 C 0.09200(19) 0.2776(4) 0.4673(4) 0.0550(13) Uani 1 1 d . . .
H27 H 0.1092 0.3178 0.4048 0.066 Uiso 1 1 calc R . .
C28 C 0.21329(19) 0.4862(4) 0.2194(4) 0.0448(11) Uani 1 1 d . . .
C29 C 0.22179(18) 0.3859(3) 0.1319(4) 0.0414(11) Uani 1 1 d . . .
H29 H 0.2243 0.4073 0.0526 0.050 Uiso 1 1 calc R . .
C30 C 0.22588(18) 0.2709(4) 0.1592(4) 0.0488(12) Uani 1 1 d . . .
H30 H 0.2272 0.2508 0.2393 0.059 Uiso 1 1 calc R . .
C31 C 0.22854(18) 0.1691(4) 0.0732(4) 0.0450(11) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C25 1.346(5) . ?
N1 C17 1.403(4) . ?
N1 C14 1.474(5) . ?
N1 C7 1.493(5) . ?
N2 C15 1.429(4) . ?
N2 C16 1.505(5) . ?
N2 C18 1.536(5) . ?
N2 H2A 0.8926 . ?
O1 C21 1.214(5) . ?
O2 C28 1.209(5) . ?
O3 C28 1.233(4) . ?
O4 C31 1.217(5) . ?
O5 C31 1.335(5) . ?
O5 H5 0.8137 . ?
C1 C2 1.381(8) . ?
C1 C6 1.426(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.525(6) . ?
C7 C8 1.467(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.362(6) . ?
C8 C13 1.415(6) . ?
C9 C10 1.320(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.365(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.339(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.554(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.524(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.543(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.506(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.528(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.478(6) . ?
C22 C27 1.415(6) . ?
C22 C23 1.434(6) . ?
C23 C24 1.409(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.396(7) . ?
C26 C27 1.387(6) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.495(6) . ?
C29 C30 1.301(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.482(6) . ?
C30 H30 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
C17 N1 C14 106.4(3) . . ?
C17 N1 C7 110.2(3) . . ?
C14 N1 C7 113.7(3) . . ?
C15 N2 C16 110.8(3) . . ?
C15 N2 C18 111.8(3) . . ?
C16 N2 C18 111.0(3) . . ?
C15 N2 H2A 101.1 . . ?
C16 N2 H2A 113.2 . . ?
C18 N2 H2A 108.5 . . ?
C31 O5 H5 109.1 . . ?
C2 C1 C6 120.8(6) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.7(7) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.1(7) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.8(7) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C1 118.3(5) . . ?
C5 C6 C7 120.0(5) . . ?
C1 C6 C7 121.6(5) . . ?
C8 C7 N1 106.4(4) . . ?
C8 C7 C6 110.7(3) . . ?
N1 C7 C6 112.1(3) . . ?
C8 C7 H7 109.2 . . ?
N1 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
C9 C8 C13 121.4(4) . . ?
C9 C8 C7 116.3(5) . . ?
C13 C8 C7 122.2(4) . . ?
C10 C9 C8 117.9(6) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 121.2(6) . . ?
C9 C10 H10A 119.4 . . ?
C11 C10 H10A 119.4 . . ?
C12 C11 C10 122.2(5) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C13 C12 C11 117.4(6) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C12 C13 C8 119.9(5) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
N1 C14 C15 111.9(3) . . ?
N1 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C14 108.3(3) . . ?
N2 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
N2 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
N2 C16 C17 114.3(3) . . ?
N2 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
N2 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
N1 C17 C16 105.8(4) . . ?
N1 C17 H17A 110.6 . . ?
C16 C17 H17A 110.6 . . ?
N1 C17 H17B 110.6 . . ?
C16 C17 H17B 110.6 . . ?
H17A C17 H17B 108.7 . . ?
N2 C18 C19 119.4(3) . . ?
N2 C18 H18A 107.5 . . ?
C19 C18 H18A 107.5 . . ?
N2 C18 H18B 107.5 . . ?
C19 C18 H18B 107.5 . . ?
H18A C18 H18B 107.0 . . ?
C20 C19 C18 114.4(4) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 111.1(4) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
O1 C21 C22 118.5(5) . . ?
O1 C21 C20 122.4(4) . . ?
C22 C21 C20 119.1(4) . . ?
C27 C22 C23 120.0(4) . . ?
C27 C22 C21 122.8(4) . . ?
C23 C22 C21 117.2(4) . . ?
C24 C23 C22 119.4(5) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C25 C24 C23 118.0(5) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
F1 C25 C24 117.0(5) . . ?
F1 C25 C26 118.7(6) . . ?
C24 C25 C26 124.3(5) . . ?
C27 C26 C25 118.6(5) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C26 C27 C22 119.7(5) . . ?
C26 C27 H27 120.2 . . ?
C22 C27 H27 120.2 . . ?
O2 C28 O3 120.9(4) . . ?
O2 C28 C29 120.5(4) . . ?
O3 C28 C29 118.6(4) . . ?
C30 C29 C28 124.5(4) . . ?
C30 C29 H29 117.7 . . ?
C28 C29 H29 117.7 . . ?
C29 C30 C31 125.4(4) . . ?
C29 C30 H30 117.3 . . ?
C31 C30 H30 117.3 . . ?
O4 C31 O5 125.2(4) . . ?
O4 C31 C30 121.3(4) . . ?
O5 C31 C30 113.5(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.89 2.43 3.231(4) 149.5 .
N2 H2A O3 0.89 1.89 2.709(4) 152.4 .
O5 H5 O2 0.81 1.73 2.528(4) 168.6 4_565
C15 H15B O3 0.97 2.35 3.307(5) 167.7 4_576
C17 H17B O4 0.97 2.42 3.127(5) 129.0 1_565
C24 H24 O1 0.93 2.56 3.429(7) 155.1 2_546
C29 H29 O5 0.93 2.48 2.796(5) 100.1 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1574459'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C77 H79 F2 N5 O11'
_chemical_formula_weight         1288.45

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   26.150(9)
_cell_length_b                   10.936(3)
_cell_length_c                   11.963(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.490(8)
_cell_angle_gamma                90.00
_cell_volume                     3391.7(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2416
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      20.03

_exptl_crystal_description       strip
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1364
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19215
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.1194
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         0.79
_diffrn_reflns_theta_max         25.03
_reflns_number_total             11510
_reflns_number_gt                5864
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2009)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3.5(13)
_refine_ls_number_reflns         11510
_refine_ls_number_parameters     875
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.26062(6) 0.18158(11) 1.01189(19) 0.0427(8) Uani 1 1 d D . .
N2 N 0.16769(10) 0.3235(2) 0.9461(2) 0.0462(8) Uani 1 1 d . . .
N3 N 0.27871(8) 0.26262(10) 0.52164(16) 0.0417(7) Uani 1 1 d D . .
N4 N 0.17777(10) 0.1503(2) 0.4639(2) 0.0447(8) Uani 1 1 d . . .
N5 N 0.72012(15) 0.0096(3) 0.7706(3) 0.0945(13) Uani 1 1 d . . .
O1 O 0.38977(12) -0.1713(3) 0.9425(4) 0.1150(14) Uani 1 1 d . . .
O2 O 0.42564(10) 0.5541(2) 0.4251(3) 0.0775(9) Uani 1 1 d . . .
O3 O 0.19485(10) 0.9014(2) 0.9479(2) 0.0675(8) Uani 1 1 d . . .
H3 H 0.2087 0.9111 1.0128 0.101 Uiso 1 1 calc R . .
O4 O 0.26305(10) 0.4716(2) 0.6437(2) 0.0666(8) Uani 1 1 d . . .
O5 O 0.30366(9) 0.4189(2) 0.8100(2) 0.0635(8) Uani 1 1 d . . .
O6 O 0.38543(9) 0.2956(2) 0.8057(2) 0.0626(8) Uani 1 1 d . . .
H6 H 0.3608 0.3423 0.7928 0.094 Uiso 1 1 calc R . .
O7 O 0.57180(10) 0.6158(2) 0.6787(3) 0.0828(9) Uani 1 1 d . . .
O8 O 0.60993(5) 0.4420(2) 0.72681(13) 0.0725(9) Uani 1 1 d D . .
O9 O 0.20570(6) 0.56265(17) 0.46830(14) 0.0677(8) Uani 1 1 d D . .
O10 O 0.23215(9) 1.0007(2) 0.14076(19) 0.0530(7) Uani 1 1 d . . .
O11 O 0.29924(8) 1.0402(2) 0.2706(2) 0.0569(7) Uani 1 1 d . . .
F1 F 0.62191(9) -0.0866(3) 0.8851(3) 0.1247(11) Uani 1 1 d . . .
F2 F 0.65068(8) 0.4014(2) 0.3573(2) 0.0931(9) Uani 1 1 d . . .
C1 C 0.57184(14) -0.0824(4) 0.9012(4) 0.0713(13) Uani 1 1 d . . .
C2 C 0.55526(15) 0.0112(3) 0.9614(3) 0.0654(12) Uani 1 1 d . . .
H2 H 0.5780 0.0716 0.9917 0.078 Uiso 1 1 calc R . .
C3 C 0.50390(13) 0.0147(3) 0.9765(3) 0.0554(11) Uani 1 1 d . . .
H3A H 0.4914 0.0802 1.0145 0.066 Uiso 1 1 calc R . .
C4 C 0.47093(13) -0.0776(3) 0.9360(3) 0.0503(10) Uani 1 1 d . . .
C5 C 0.48963(16) -0.1729(4) 0.8767(3) 0.0688(13) Uani 1 1 d . . .
H5 H 0.4672 -0.2349 0.8485 0.083 Uiso 1 1 calc R . .
C6 C 0.54035(17) -0.1782(4) 0.8584(4) 0.0773(13) Uani 1 1 d . . .
H6A H 0.5530 -0.2426 0.8192 0.093 Uiso 1 1 calc R . .
C7 C 0.41495(14) -0.0790(3) 0.9532(3) 0.0573(11) Uani 1 1 d . . .
C8 C 0.39196(12) 0.0392(3) 0.9835(3) 0.0517(10) Uani 1 1 d . . .
H8A H 0.4026 0.1025 0.9346 0.062 Uiso 1 1 calc R . .
H8B H 0.4061 0.0598 1.0602 0.062 Uiso 1 1 calc R . .
C9 C 0.33422(13) 0.0407(3) 0.9750(3) 0.0547(10) Uani 1 1 d . . .
H9A H 0.3226 -0.0226 1.0226 0.066 Uiso 1 1 calc R . .
H9B H 0.3192 0.0254 0.8978 0.066 Uiso 1 1 calc R . .
C10 C 0.31759(12) 0.1650(3) 1.0126(3) 0.0526(10) Uani 1 1 d . . .
H10A H 0.3345 0.1799 1.0885 0.063 Uiso 1 1 calc R . .
H10B H 0.3298 0.2266 0.9640 0.063 Uiso 1 1 calc R . .
C11 C 0.24948(13) 0.3020(3) 1.0642(3) 0.0515(10) Uani 1 1 d . . .
H11A H 0.2658 0.3038 1.1418 0.062 Uiso 1 1 calc R . .
H11B H 0.2640 0.3676 1.0239 0.062 Uiso 1 1 calc R . .
C12 C 0.19258(13) 0.3222(3) 1.0614(3) 0.0543(11) Uani 1 1 d . . .
H12A H 0.1780 0.2576 1.1028 0.065 Uiso 1 1 calc R . .
H12B H 0.1866 0.3995 1.0973 0.065 Uiso 1 1 calc R . .
C13 C 0.17550(13) 0.2023(3) 0.8976(3) 0.0525(11) Uani 1 1 d . . .
H13A H 0.1573 0.1982 0.8216 0.063 Uiso 1 1 calc R . .
H13B H 0.1615 0.1398 0.9424 0.063 Uiso 1 1 calc R . .
C14 C 0.23217(12) 0.1785(3) 0.8946(3) 0.0481(10) Uani 1 1 d . . .
H14A H 0.2367 0.0991 0.8610 0.058 Uiso 1 1 calc R . .
H14B H 0.2461 0.2401 0.8487 0.058 Uiso 1 1 calc R . .
C15 C 0.11235(13) 0.3510(3) 0.9348(3) 0.0539(11) Uani 1 1 d . . .
H15 H 0.0948 0.2819 0.9654 0.065 Uiso 1 1 calc R . .
C16 C 0.08999(14) 0.3678(3) 0.8139(3) 0.0545(11) Uani 1 1 d . . .
C17 C 0.11791(16) 0.4174(3) 0.7346(3) 0.0663(13) Uani 1 1 d . . .
H17 H 0.1527 0.4342 0.7553 0.080 Uiso 1 1 calc R . .
C18 C 0.09647(19) 0.4426(4) 0.6276(4) 0.0878(16) Uani 1 1 d . . .
H18 H 0.1157 0.4788 0.5764 0.105 Uiso 1 1 calc R . .
C19 C 0.0446(2) 0.4124(4) 0.5967(5) 0.119(2) Uani 1 1 d . . .
H19 H 0.0289 0.4289 0.5240 0.142 Uiso 1 1 calc R . .
C20 C 0.0174(2) 0.3600(5) 0.6708(5) 0.121(2) Uani 1 1 d . . .
H20 H -0.0168 0.3388 0.6487 0.145 Uiso 1 1 calc R . .
C21 C 0.03983(16) 0.3367(4) 0.7803(4) 0.0818(15) Uani 1 1 d . . .
H21 H 0.0206 0.2997 0.8310 0.098 Uiso 1 1 calc R . .
C22 C 0.10180(12) 0.4645(3) 1.0007(3) 0.0498(10) Uani 1 1 d . . .
C23 C 0.07443(14) 0.4575(4) 1.0919(4) 0.0755(14) Uani 1 1 d . . .
H23 H 0.0639 0.3817 1.1158 0.091 Uiso 1 1 calc R . .
C24 C 0.06236(15) 0.5637(5) 1.1485(4) 0.0825(15) Uani 1 1 d . . .
H24 H 0.0436 0.5574 1.2091 0.099 Uiso 1 1 calc R . .
C25 C 0.07764(14) 0.6756(4) 1.1165(4) 0.0877(16) Uani 1 1 d . . .
H25 H 0.0702 0.7458 1.1552 0.105 Uiso 1 1 calc R . .
C26 C 0.10460(15) 0.6819(4) 1.0247(4) 0.0800(15) Uani 1 1 d . . .
H26 H 0.1149 0.7579 1.0008 0.096 Uiso 1 1 calc R . .
C27 C 0.11645(15) 0.5796(3) 0.9684(4) 0.0629(12) Uani 1 1 d . . .
H27 H 0.1347 0.5872 0.9071 0.076 Uiso 1 1 calc R . .
C28 C 0.60098(14) 0.4133(4) 0.3793(4) 0.0675(13) Uani 1 1 d . . .
C29 C 0.57945(15) 0.3189(4) 0.4337(4) 0.0679(13) Uani 1 1 d . . .
H29 H 0.5983 0.2490 0.4559 0.082 Uiso 1 1 calc R . .
C30 C 0.52871(14) 0.3315(3) 0.4542(3) 0.0522(10) Uani 1 1 d . . .
H30 H 0.5128 0.2688 0.4893 0.063 Uiso 1 1 calc R . .
C31 C 0.50176(13) 0.4379(3) 0.4222(3) 0.0475(10) Uani 1 1 d . . .
C32 C 0.52512(14) 0.5305(3) 0.3682(3) 0.0574(11) Uani 1 1 d . . .
H32 H 0.5071 0.6018 0.3467 0.069 Uiso 1 1 calc R . .
C33 C 0.57512(15) 0.5164(4) 0.3465(3) 0.0601(11) Uani 1 1 d . . .
H33 H 0.5910 0.5776 0.3094 0.072 Uiso 1 1 calc R . .
C34 C 0.44605(13) 0.4534(3) 0.4405(3) 0.0472(10) Uani 1 1 d . . .
C35 C 0.41639(12) 0.3478(3) 0.4755(3) 0.0468(10) Uani 1 1 d . . .
H35A H 0.4312 0.3236 0.5508 0.056 Uiso 1 1 calc R . .
H35B H 0.4207 0.2799 0.4254 0.056 Uiso 1 1 calc R . .
C36 C 0.35927(13) 0.3698(3) 0.4758(3) 0.0556(11) Uani 1 1 d . . .
H36A H 0.3540 0.4364 0.5266 0.067 Uiso 1 1 calc R . .
H36B H 0.3434 0.3919 0.4007 0.067 Uiso 1 1 calc R . .
C37 C 0.33511(12) 0.2545(3) 0.5137(3) 0.0510(10) Uani 1 1 d . . .
H37A H 0.3407 0.1894 0.4615 0.061 Uiso 1 1 calc R . .
H37B H 0.3528 0.2318 0.5870 0.061 Uiso 1 1 calc R . .
C38 C 0.26199(12) 0.1517(3) 0.5777(3) 0.0500(10) Uani 1 1 d . . .
H38A H 0.2788 0.1492 0.6549 0.060 Uiso 1 1 calc R . .
H38B H 0.2725 0.0798 0.5391 0.060 Uiso 1 1 calc R . .
C39 C 0.20385(13) 0.1489(3) 0.5776(3) 0.0512(10) Uani 1 1 d . . .
H39A H 0.1943 0.0758 0.6158 0.061 Uiso 1 1 calc R . .
H39B H 0.1933 0.2193 0.6183 0.061 Uiso 1 1 calc R . .
C40 C 0.19035(13) 0.2676(3) 0.4154(3) 0.0523(11) Uani 1 1 d . . .
H40A H 0.1801 0.3336 0.4620 0.063 Uiso 1 1 calc R . .
H40B H 0.1712 0.2760 0.3408 0.063 Uiso 1 1 calc R . .
C41 C 0.24720(13) 0.2773(3) 0.4076(3) 0.0492(10) Uani 1 1 d . . .
H41A H 0.2545 0.3564 0.3764 0.059 Uiso 1 1 calc R . .
H41B H 0.2570 0.2147 0.3570 0.059 Uiso 1 1 calc R . .
C42 C 0.12113(13) 0.1342(3) 0.4599(3) 0.0512(10) Uani 1 1 d . . .
H42 H 0.1071 0.2051 0.4957 0.061 Uiso 1 1 calc R . .
C43 C 0.10837(12) 0.0212(3) 0.5211(3) 0.0485(10) Uani 1 1 d . . .
C44 C 0.07876(14) 0.0290(4) 0.6080(4) 0.0731(13) Uani 1 1 d . . .
H44 H 0.0679 0.1049 0.6308 0.088 Uiso 1 1 calc R . .
C45 C 0.06511(16) -0.0768(5) 0.6618(4) 0.0916(16) Uani 1 1 d . . .
H45 H 0.0457 -0.0708 0.7214 0.110 Uiso 1 1 calc R . .
C46 C 0.08000(16) -0.1899(4) 0.6276(4) 0.0849(16) Uani 1 1 d . . .
H46 H 0.0705 -0.2603 0.6634 0.102 Uiso 1 1 calc R . .
C47 C 0.10921(16) -0.1980(4) 0.5394(4) 0.0738(14) Uani 1 1 d . . .
H47 H 0.1189 -0.2740 0.5143 0.089 Uiso 1 1 calc R . .
C48 C 0.12386(15) -0.0926(4) 0.4891(4) 0.0658(13) Uani 1 1 d . . .
H48 H 0.1448 -0.0984 0.4321 0.079 Uiso 1 1 calc R . .
C49 C 0.09532(12) 0.1262(3) 0.3378(3) 0.0457(10) Uani 1 1 d . . .
C50 C 0.04525(14) 0.1685(4) 0.3105(4) 0.0647(12) Uani 1 1 d . . .
H50 H 0.0292 0.2085 0.3650 0.078 Uiso 1 1 calc R . .
C51 C 0.01921(16) 0.1525(4) 0.2050(4) 0.0844(16) Uani 1 1 d . . .
H51 H -0.0145 0.1809 0.1887 0.101 Uiso 1 1 calc R . .
C52 C 0.04232(15) 0.0948(4) 0.1229(4) 0.0752(14) Uani 1 1 d . . .
H52 H 0.0245 0.0833 0.0512 0.090 Uiso 1 1 calc R . .
C53 C 0.09205(16) 0.0545(4) 0.1486(4) 0.0696(13) Uani 1 1 d . . .
H53 H 0.1080 0.0155 0.0934 0.083 Uiso 1 1 calc R . .
C54 C 0.11897(14) 0.0705(3) 0.2551(3) 0.0565(11) Uani 1 1 d . . .
H54 H 0.1529 0.0438 0.2707 0.068 Uiso 1 1 calc R . .
C55 C 0.21603(13) 0.8023(3) 0.9016(3) 0.0480(10) Uani 1 1 d . . .
C56 C 0.20199(15) 0.7788(3) 0.7921(3) 0.0570(11) Uani 1 1 d . . .
H56 H 0.1788 0.8314 0.7507 0.068 Uiso 1 1 calc R . .
C57 C 0.22047(14) 0.6800(3) 0.7381(3) 0.0588(11) Uani 1 1 d . . .
H57 H 0.2105 0.6667 0.6616 0.071 Uiso 1 1 calc R . .
C58 C 0.25461(12) 0.6005(3) 0.8013(3) 0.0405(9) Uani 1 1 d . . .
C59 C 0.26880(14) 0.6249(3) 0.9106(3) 0.0574(11) Uani 1 1 d . . .
H59 H 0.2922 0.5730 0.9522 0.069 Uiso 1 1 calc R . .
C60 C 0.25017(16) 0.7239(3) 0.9639(3) 0.0648(13) Uani 1 1 d . . .
H60 H 0.2603 0.7377 1.0403 0.078 Uiso 1 1 calc R . .
C61 C 0.27499(13) 0.4900(3) 0.7480(3) 0.0469(10) Uani 1 1 d . . .
C62 C 0.42906(13) 0.3530(3) 0.7839(3) 0.0456(10) Uani 1 1 d . . .
C63 C 0.42941(14) 0.4726(3) 0.7450(3) 0.0505(10) Uani 1 1 d . . .
H63 H 0.3994 0.5191 0.7362 0.061 Uiso 1 1 calc R . .
C64 C 0.47524(14) 0.5212(3) 0.7196(3) 0.0530(11) Uani 1 1 d . . .
H64 H 0.4755 0.6004 0.6914 0.064 Uiso 1 1 calc R . .
C65 C 0.52133(13) 0.4550(3) 0.7351(3) 0.0434(9) Uani 1 1 d . . .
C66 C 0.51991(14) 0.3385(3) 0.7761(3) 0.0485(10) Uani 1 1 d . . .
H66 H 0.5501 0.2926 0.7872 0.058 Uiso 1 1 calc R . .
C67 C 0.47475(13) 0.2883(3) 0.8012(3) 0.0478(10) Uani 1 1 d . . .
H67 H 0.4749 0.2095 0.8303 0.057 Uiso 1 1 calc R . .
C68 C 0.56932(14) 0.5129(3) 0.7088(3) 0.0493(10) Uani 1 1 d . . .
C69 C 0.22034(14) 0.6634(3) 0.4156(3) 0.0511(10) Uani 1 1 d . . .
C70 C 0.19151(14) 0.6945(3) 0.3158(3) 0.0547(11) Uani 1 1 d . . .
H70 H 0.1632 0.6468 0.2879 0.066 Uiso 1 1 calc R . .
C71 C 0.20400(13) 0.7962(3) 0.2560(3) 0.0466(10) Uani 1 1 d . . .
H71 H 0.1843 0.8167 0.1881 0.056 Uiso 1 1 calc R . .
C72 C 0.24647(13) 0.8679(3) 0.2982(3) 0.0415(9) Uani 1 1 d . . .
C73 C 0.27492(14) 0.8361(3) 0.3979(3) 0.0503(10) Uani 1 1 d . . .
H73 H 0.3034 0.8828 0.4262 0.060 Uiso 1 1 calc R . .
C74 C 0.26166(15) 0.7352(3) 0.4568(3) 0.0537(11) Uani 1 1 d . . .
H74 H 0.2809 0.7155 0.5253 0.064 Uiso 1 1 calc R . .
C75 C 0.26018(13) 0.9768(3) 0.2326(3) 0.0431(9) Uani 1 1 d . . .
C76 C 0.64923(17) 0.1712(4) 0.7864(5) 0.0964(18) Uani 1 1 d . . .
H76A H 0.6190 0.1301 0.8047 0.145 Uiso 1 1 calc R . .
H76B H 0.6411 0.2140 0.7163 0.145 Uiso 1 1 calc R . .
H76C H 0.6610 0.2284 0.8450 0.145 Uiso 1 1 calc R . .
C77 C 0.68965(18) 0.0815(4) 0.7759(4) 0.0794(15) Uani 1 1 d . . .
H3' H 0.2700(2) 0.3290(3) 0.5577(4) 0.084(13) Uiso 1 1 d D . .
H1' H 0.24314(12) 0.1182(3) 1.0340(6) 0.084(13) Uiso 1 1 d D . .
H9 H 0.22787(11) 0.5350(6) 0.5204(3) 0.081(13) Uiso 1 1 d D . .
H8 H 0.63067(9) 0.4565(10) 0.6793(3) 0.045(9) Uiso 1 1 d 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
N1 C14 1.500(4) . ?
N1 C10 1.499(4) . ?
N1 C11 1.503(4) . ?
N2 C12 1.446(4) . ?
N2 C15 1.467(4) . ?
N2 C13 1.472(4) . ?
N3 C38 1.480(4) . ?
N3 C37 1.493(4) . ?
N3 C41 1.508(4) . ?
N4 C39 1.440(4) . ?
N4 C40 1.462(4) . ?
N4 C42 1.486(4) . ?
N5 C77 1.127(5) . ?
O1 C7 1.203(4) . ?
O2 C34 1.228(4) . ?
O3 C55 1.367(4) . ?
O4 C61 1.263(4) . ?
O5 C61 1.253(4) . ?
O6 C62 1.357(4) . ?
O7 C68 1.186(4) . ?
O8 C68 1.310(4) . ?
O9 C69 1.350(4) . ?
O10 C75 1.265(4) . ?
O11 C75 1.269(4) . ?
F1 C1 1.349(4) . ?
F2 C28 1.365(4) . ?
C1 C2 1.354(6) . ?
C1 C6 1.388(6) . ?
C2 C3 1.379(5) . ?
C3 C4 1.374(5) . ?
C4 C5 1.385(5) . ?
C4 C7 1.504(5) . ?
C5 C6 1.373(6) . ?
C7 C8 1.490(5) . ?
C8 C9 1.500(4) . ?
C9 C10 1.513(5) . ?
C11 C12 1.500(5) . ?
C13 C14 1.509(5) . ?
C15 C16 1.499(5) . ?
C15 C22 1.515(5) . ?
C16 C21 1.364(5) . ?
C16 C17 1.381(6) . ?
C17 C18 1.357(6) . ?
C18 C19 1.399(7) . ?
C19 C20 1.335(8) . ?
C20 C21 1.387(7) . ?
C22 C23 1.383(6) . ?
C22 C27 1.385(5) . ?
C23 C24 1.401(6) . ?
C24 C25 1.357(6) . ?
C25 C26 1.382(7) . ?
C26 C27 1.362(6) . ?
C28 C33 1.346(5) . ?
C28 C29 1.379(6) . ?
C29 C30 1.387(5) . ?
C30 C31 1.388(5) . ?
C31 C32 1.386(5) . ?
C31 C34 1.511(5) . ?
C32 C33 1.375(5) . ?
C34 C35 1.481(5) . ?
C35 C36 1.513(5) . ?
C36 C37 1.506(5) . ?
C38 C39 1.520(5) . ?
C40 C41 1.505(5) . ?
C42 C43 1.496(5) . ?
C42 C49 1.529(5) . ?
C43 C48 1.378(5) . ?
C43 C44 1.378(5) . ?
C44 C45 1.392(7) . ?
C45 C46 1.376(7) . ?
C46 C47 1.383(7) . ?
C47 C48 1.377(6) . ?
C49 C54 1.375(5) . ?
C49 C50 1.387(5) . ?
C50 C51 1.365(6) . ?
C51 C52 1.372(6) . ?
C52 C53 1.370(5) . ?
C53 C54 1.385(5) . ?
C55 C56 1.338(5) . ?
C55 C60 1.384(5) . ?
C56 C57 1.378(5) . ?
C57 C58 1.396(5) . ?
C58 C59 1.338(5) . ?
C58 C61 1.496(4) . ?
C59 C60 1.377(5) . ?
C62 C67 1.380(5) . ?
C62 C63 1.389(5) . ?
C63 C64 1.380(5) . ?
C64 C65 1.397(5) . ?
C65 C66 1.367(5) . ?
C65 C68 1.476(5) . ?
C66 C67 1.371(5) . ?
C69 C70 1.369(5) . ?
C69 C74 1.374(5) . ?
C70 C71 1.384(5) . ?
C71 C72 1.399(5) . ?
C72 C73 1.366(5) . ?
C72 C75 1.496(4) . ?
C73 C74 1.377(5) . ?
C76 C77 1.459(6) . ?

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
C14 N1 C10 112.0(2) . . ?
C14 N1 C11 108.1(2) . . ?
C10 N1 C11 110.5(2) . . ?
C12 N2 C15 113.9(3) . . ?
C12 N2 C13 107.4(3) . . ?
C15 N2 C13 109.5(3) . . ?
C38 N3 C37 109.5(2) . . ?
C38 N3 C41 109.8(2) . . ?
C37 N3 C41 112.1(2) . . ?
C39 N4 C40 106.3(3) . . ?
C39 N4 C42 112.1(3) . . ?
C40 N4 C42 111.5(3) . . ?
F1 C1 C2 119.1(4) . . ?
F1 C1 C6 117.5(4) . . ?
C2 C1 C6 123.4(4) . . ?
C1 C2 C3 118.4(4) . . ?
C2 C3 C4 120.7(3) . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 C7 122.4(3) . . ?
C5 C4 C7 118.5(3) . . ?
C6 C5 C4 121.8(4) . . ?
C5 C6 C1 116.6(4) . . ?
O1 C7 C8 121.4(3) . . ?
O1 C7 C4 121.5(3) . . ?
C8 C7 C4 117.1(3) . . ?
C7 C8 C9 115.3(3) . . ?
C8 C9 C10 108.4(3) . . ?
N1 C10 C9 115.5(3) . . ?
C12 C11 N1 111.4(3) . . ?
N2 C12 C11 110.2(3) . . ?
N2 C13 C14 110.6(3) . . ?
N1 C14 C13 110.1(3) . . ?
N2 C15 C16 111.7(3) . . ?
N2 C15 C22 111.4(3) . . ?
C16 C15 C22 109.1(3) . . ?
C21 C16 C17 118.0(4) . . ?
C21 C16 C15 119.5(4) . . ?
C17 C16 C15 122.4(3) . . ?
C18 C17 C16 122.5(4) . . ?
C17 C18 C19 118.0(5) . . ?
C20 C19 C18 120.5(5) . . ?
C19 C20 C21 120.7(5) . . ?
C16 C21 C20 120.3(5) . . ?
C23 C22 C27 117.4(4) . . ?
C23 C22 C15 120.9(3) . . ?
C27 C22 C15 121.6(3) . . ?
C22 C23 C24 120.5(4) . . ?
C25 C24 C23 121.1(4) . . ?
C24 C25 C26 118.0(4) . . ?
C27 C26 C25 121.6(4) . . ?
C26 C27 C22 121.3(4) . . ?
C33 C28 F2 118.6(4) . . ?
C33 C28 C29 122.9(4) . . ?
F2 C28 C29 118.5(4) . . ?
C28 C29 C30 117.9(4) . . ?
C29 C30 C31 119.8(3) . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 C34 121.2(3) . . ?
C32 C31 C34 118.5(3) . . ?
C33 C32 C31 119.6(3) . . ?
C28 C33 C32 119.6(4) . . ?
O2 C34 C35 120.6(3) . . ?
O2 C34 C31 119.2(3) . . ?
C35 C34 C31 120.3(3) . . ?
C34 C35 C36 115.5(3) . . ?
C37 C36 C35 108.7(3) . . ?
N3 C37 C36 115.2(3) . . ?
N3 C38 C39 111.7(3) . . ?
N4 C39 C38 110.6(3) . . ?
N4 C40 C41 111.2(3) . . ?
C40 C41 N3 111.3(3) . . ?
N4 C42 C43 111.5(3) . . ?
N4 C42 C49 110.6(3) . . ?
C43 C42 C49 108.7(3) . . ?
C48 C43 C44 118.7(4) . . ?
C48 C43 C42 121.2(3) . . ?
C44 C43 C42 120.1(3) . . ?
C43 C44 C45 120.0(4) . . ?
C46 C45 C44 120.7(4) . . ?
C45 C46 C47 119.3(4) . . ?
C48 C47 C46 119.5(4) . . ?
C43 C48 C47 121.7(4) . . ?
C54 C49 C50 118.5(3) . . ?
C54 C49 C42 121.9(3) . . ?
C50 C49 C42 119.4(3) . . ?
C51 C50 C49 121.1(4) . . ?
C52 C51 C50 120.5(4) . . ?
C51 C52 C53 118.8(4) . . ?
C52 C53 C54 121.3(4) . . ?
C49 C54 C53 119.7(4) . . ?
C56 C55 O3 118.3(3) . . ?
C56 C55 C60 119.0(3) . . ?
O3 C55 C60 122.7(3) . . ?
C55 C56 C57 122.7(3) . . ?
C56 C57 C58 118.2(3) . . ?
C59 C58 C57 118.7(3) . . ?
C59 C58 C61 120.6(3) . . ?
C57 C58 C61 120.7(3) . . ?
C58 C59 C60 122.7(3) . . ?
C59 C60 C55 118.7(4) . . ?
O5 C61 O4 122.5(3) . . ?
O5 C61 C58 117.9(3) . . ?
O4 C61 C58 119.6(3) . . ?
O6 C62 C67 117.9(3) . . ?
O6 C62 C63 122.8(3) . . ?
C67 C62 C63 119.3(3) . . ?
C64 C63 C62 118.7(3) . . ?
C63 C64 C65 122.0(3) . . ?
C66 C65 C64 117.9(3) . . ?
C66 C65 C68 122.7(3) . . ?
C64 C65 C68 119.5(3) . . ?
C67 C66 C65 121.1(3) . . ?
C66 C67 C62 121.0(3) . . ?
O7 C68 O8 122.4(3) . . ?
O7 C68 C65 123.6(3) . . ?
O8 C68 C65 113.9(3) . . ?
O9 C69 C70 116.9(3) . . ?
O9 C69 C74 123.8(3) . . ?
C70 C69 C74 119.3(3) . . ?
C69 C70 C71 120.7(3) . . ?
C70 C71 C72 119.6(3) . . ?
C73 C72 C71 119.3(3) . . ?
C73 C72 C75 121.4(3) . . ?
C71 C72 C75 119.3(3) . . ?
C72 C73 C74 120.4(3) . . ?
C69 C74 C73 120.9(3) . . ?
O10 C75 O11 123.1(3) . . ?
O10 C75 C72 117.9(3) . . ?
O11 C75 C72 118.9(3) . . ?
N5 C77 C76 177.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1574458'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H35 F N2 O4'
_chemical_formula_weight         554.64

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.735(2)
_cell_length_b                   27.547(6)
_cell_length_c                   12.463(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.484(7)
_cell_angle_gamma                90
_cell_volume                     2989.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1420
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      18.77

_exptl_crystal_description       strip
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19838
_diffrn_reflns_av_unetI/netI     0.1319
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.478
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6828
_reflns_number_gt                2074
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2009)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2009)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0128P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6828
_refine_ls_number_parameters     431
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.2199
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6592(4) 0.60029(12) 0.5789(3) 0.0868(10) Uani 1 1 d . . . A 4
C2 C 0.5133(5) 0.61532(11) 0.5697(3) 0.0941(10) Uani 1 1 d . . . A 4
H2 H 0.4783 0.6380 0.6172 0.113 Uiso 1 1 calc R U . A 4
C3 C 0.4155(4) 0.59624(11) 0.4875(2) 0.0882(10) Uani 1 1 d . . . A 4
H3 H 0.3136 0.6063 0.4796 0.106 Uiso 1 1 calc R U . A 4
C4 C 0.4677(4) 0.56234(10) 0.4171(2) 0.0676(8) Uani 1 1 d . . . A 4
C5 C 0.6202(4) 0.54821(10) 0.4301(2) 0.0784(9) Uani 1 1 d . . . A 4
H5 H 0.6575 0.5259 0.3825 0.094 Uiso 1 1 calc R U . A 4
C6 C 0.7177(4) 0.56674(12) 0.5127(3) 0.0946(10) Uani 1 1 d . . . A 4
H6 H 0.8195 0.5567 0.5228 0.113 Uiso 1 1 calc R U . A 4
C7 C 0.3576(4) 0.54296(10) 0.3308(2) 0.0732(8) Uani 1 1 d . . . A 4
C8 C 0.4107(3) 0.50502(9) 0.2567(2) 0.0696(8) Uani 1 1 d . . . A 4
H8A H 0.4549 0.4783 0.2993 0.083 Uiso 1 1 calc R U . A 4
H8B H 0.4910 0.5186 0.2164 0.083 Uiso 1 1 calc R U . A 4
C9 C 0.2841(3) 0.48535(9) 0.17791(19) 0.0675(8) Uani 1 1 d . . . A 4
H9A H 0.2010 0.4727 0.2170 0.081 Uiso 1 1 calc R U . A 4
H9B H 0.2436 0.5112 0.1311 0.081 Uiso 1 1 calc R U . A 4
C10 C 0.3489(3) 0.44524(9) 0.1112(2) 0.0679(8) Uani 1 1 d . . . A 4
H10A H 0.4474 0.4557 0.0886 0.081 Uiso 1 1 calc R U . A 4
H10B H 0.3669 0.4168 0.1564 0.081 Uiso 1 1 calc R U . A 4
C11 C 0.0933(3) 0.41449(9) 0.0381(2) 0.0644(8) Uani 1 1 d . . . A 4
H11A H 0.0406 0.4406 0.0724 0.077 Uiso 1 1 calc R U . A 4
H11B H 0.1031 0.3874 0.0879 0.077 Uiso 1 1 calc R U . A 4
C12 C 0.0004(3) 0.39913(9) -0.0625(2) 0.0648(8) Uani 1 1 d . . . A 4
H12A H -0.1007 0.3888 -0.0447 0.078 Uiso 1 1 calc R U . A 4
H12B H -0.0122 0.4264 -0.1115 0.078 Uiso 1 1 calc R U . A 4
C13 C 0.2243(3) 0.37768(8) -0.14646(19) 0.0591(7) Uani 1 1 d . . . A 4
H13A H 0.2063 0.4052 -0.1944 0.071 Uiso 1 1 calc R U . A 4
H13B H 0.2764 0.3527 -0.1846 0.071 Uiso 1 1 calc R U . A 4
C14 C 0.3237(3) 0.39310(8) -0.0481(2) 0.0608(7) Uani 1 1 d . . . A 4
H14A H 0.3457 0.3651 -0.0022 0.073 Uiso 1 1 calc R U . A 4
H14B H 0.4205 0.4055 -0.0700 0.073 Uiso 1 1 calc R U . A 4
C15 C -0.0216(3) 0.34167(9) -0.2093(2) 0.0618(7) Uani 1 1 d . . . A 4
H15 H -0.0519 0.3699 -0.2539 0.074 Uiso 1 1 calc R U . A 4
C16 C -0.1657(3) 0.31804(10) -0.1749(3) 0.0721(8) Uani 1 1 d . . . A 4
C17 C -0.1703(4) 0.29366(11) -0.0794(3) 0.0914(10) Uani 1 1 d . . . A 4
H17 H -0.0829 0.2925 -0.0318 0.110 Uiso 1 1 calc R U . A 4
C18 C -0.3056(5) 0.27029(14) -0.0523(4) 0.1275(15) Uani 1 1 d . . . A 4
H18 H -0.3087 0.2540 0.0129 0.153 Uiso 1 1 calc R U . A 4
C19 C -0.4313(7) 0.27214(18) -0.1236(5) 0.150(3) Uani 1 1 d . U . A 4
H19 H -0.5211 0.2567 -0.1067 0.180 Uiso 1 1 calc R U . A 4
C20 C -0.4291(5) 0.29578(17) -0.2183(5) 0.142(2) Uani 1 1 d . U . A 4
H20 H -0.5165 0.2962 -0.2660 0.171 Uiso 1 1 calc R U . A 4
C21 C -0.2973(4) 0.31946(11) -0.2448(3) 0.1027(11) Uani 1 1 d . . . A 4
H21 H -0.2970 0.3363 -0.3094 0.123 Uiso 1 1 calc R U . A 4
C22 C 0.0650(3) 0.30696(9) -0.2773(2) 0.0565(7) Uani 1 1 d . . . A 4
C23 C 0.1020(4) 0.32050(11) -0.3788(3) 0.0840(10) Uani 1 1 d . . . A 4
H23 H 0.0741 0.3511 -0.4048 0.101 Uiso 1 1 calc R U . A 4
C24 C 0.1791(4) 0.28967(14) -0.4419(3) 0.1035(11) Uani 1 1 d . . . A 4
H24 H 0.2043 0.2997 -0.5096 0.124 Uiso 1 1 calc R U . A 4
C25 C 0.2188(4) 0.24453(13) -0.4059(3) 0.0939(11) Uani 1 1 d . . . A 4
H25 H 0.2696 0.2234 -0.4493 0.113 Uiso 1 1 calc R U . A 4
C26 C 0.1841(3) 0.23031(10) -0.3060(3) 0.0835(9) Uani 1 1 d . . . A 4
H26 H 0.2126 0.1996 -0.2805 0.100 Uiso 1 1 calc R U . A 4
C27 C 0.1066(3) 0.26152(10) -0.2428(2) 0.0686(8) Uani 1 1 d . . . A 4
H27 H 0.0821 0.2514 -0.1751 0.082 Uiso 1 1 calc R U . A 4
F1 F 0.7544(2) 0.61891(7) 0.66086(15) 0.1264(7) Uani 1 1 d . . . A 4
N1 N 0.0771(2) 0.35893(7) -0.11523(16) 0.0542(5) Uani 1 1 d . . . A 4
N2 N 0.2481(2) 0.43117(6) 0.01376(16) 0.0551(6) Uani 1 1 d . . . A 4
H2A H 0.2388 0.4590 -0.0240 0.083 Uiso 1 1 d R U . A 4
O1 O 0.2247(3) 0.55693(8) 0.32220(16) 0.1080(8) Uani 1 1 d . . . A 4
C28 C 0.7893(14) 0.4186(2) 0.1929(7) 0.061(4) Uani 0.582(7) 1 d G . P B 1
C29 C 0.8681(14) 0.4256(3) 0.2929(8) 0.077(4) Uani 0.582(7) 1 d G . P B 1
C30 C 0.8916(10) 0.3869(5) 0.3637(5) 0.094(4) Uani 0.582(7) 1 d G . P B 1
H30 H 0.9443 0.3916 0.4306 0.113 Uiso 0.582(7) 1 calc R U P B 1
C31 C 0.8363(12) 0.3411(4) 0.3345(10) 0.111(4) Uani 0.582(7) 1 d G . P B 1
H31 H 0.8520 0.3151 0.3819 0.134 Uiso 0.582(7) 1 calc R U P B 1
C32 C 0.7575(14) 0.33398(18) 0.2344(11) 0.109(4) Uani 0.582(7) 1 d G . P B 1
H32 H 0.7205 0.3033 0.2149 0.131 Uiso 0.582(7) 1 calc R U P B 1
C33 C 0.7340(12) 0.3727(3) 0.1636(6) 0.064(2) Uani 0.582(7) 1 d G . P B 1
H33 H 0.6813 0.3680 0.0967 0.077 Uiso 0.582(7) 1 calc R U P B 1
C34 C 0.7511(9) 0.4579(4) 0.1109(10) 0.065(2) Uani 0.582(7) 1 d . . P B 1
O2 O 0.6777(5) 0.4477(2) 0.0255(4) 0.0847(18) Uani 0.582(7) 1 d . . P B 1
O3 O 0.8058(8) 0.49763(16) 0.1374(8) 0.0871(19) Uani 0.582(7) 1 d . . P B 1
O4 O 0.9101(8) 0.4698(3) 0.3202(6) 0.105(2) Uani 0.582(7) 1 d . . P B 1
H4 H 0.8868 0.4883 0.2701 0.158 Uiso 0.582(7) 1 calc R U P B 1
C28' C 0.786(3) 0.4248(4) 0.2142(18) 0.075(7) Uani 0.418(7) 1 d G . P B 2
C29' C 0.863(2) 0.4107(4) 0.3112(16) 0.063(4) Uani 0.418(7) 1 d G . P B 2
C30' C 0.8697(15) 0.3618(6) 0.3393(8) 0.082(4) Uani 0.418(7) 1 d G . P B 2
H30' H 0.9209 0.3523 0.4041 0.098 Uiso 0.418(7) 1 calc R U P B 2
C31' C 0.8004(18) 0.3272(2) 0.2704(14) 0.100(5) Uani 0.418(7) 1 d G . P B 2
H31' H 0.8052 0.2945 0.2892 0.120 Uiso 0.418(7) 1 calc R U P B 2
C32' C 0.7239(16) 0.3414(7) 0.1735(12) 0.112(6) Uani 0.418(7) 1 d G . P B 2
H32' H 0.6776 0.3182 0.1274 0.135 Uiso 0.418(7) 1 calc R U P B 2
C33' C 0.717(2) 0.3902(8) 0.1454(9) 0.133(9) Uani 0.418(7) 1 d G . P B 2
H33' H 0.6655 0.3997 0.0806 0.159 Uiso 0.418(7) 1 calc R U P B 2
C34' C 0.7873(15) 0.4750(5) 0.1706(14) 0.065(2) Uani 0.418(7) 1 d . . P B 2
O2' O 0.7250(10) 0.4837(4) 0.0741(8) 0.083(3) Uani 0.418(7) 1 d . . P B 2
O3' O 0.8414(6) 0.5074(2) 0.2293(7) 0.084(3) Uani 0.418(7) 1 d . . P B 2
O4' O 0.9381(10) 0.4479(5) 0.3709(7) 0.113(3) Uani 0.418(7) 1 d . . P B 2
H4' H 0.9284 0.4436 0.4351 0.169 Uiso 0.418(7) 1 calc R U P B 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.337(4) . ?
C1 C6 1.364(4) . ?
C1 F1 1.365(3) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 C7 1.485(4) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.220(3) . ?
C7 C8 1.492(3) . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.495(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.482(3) . ?
C11 C12 1.500(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.475(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.466(3) . ?
C13 C14 1.507(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.487(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N1 1.479(3) . ?
C15 C16 1.509(4) . ?
C15 C22 1.518(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.369(4) . ?
C16 C21 1.387(4) . ?
C17 C18 1.410(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.350(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.364(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.370(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.362(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.379(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
N2 H2A 0.9001 . ?
C28 C29 1.3900 . ?
C28 C33 1.3900 . ?
C28 C34 1.508(11) . ?
C29 O4 1.308(11) . ?
C29 C30 1.3900 . ?
C30 C31 1.3900 . ?
C30 H30 0.9300 . ?
C31 C32 1.3900 . ?
C31 H31 0.9300 . ?
C32 C33 1.3900 . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 O3 1.230(14) . ?
C34 O2 1.231(12) . ?
O4 H4 0.8200 . ?
C28' C29' 1.3900 . ?
C28' C33' 1.3900 . ?
C28' C34' 1.486(14) . ?
C29' C30' 1.3900 . ?
C29' O4' 1.401(17) . ?
C30' C31' 1.3900 . ?
C30' H30' 0.9300 . ?
C31' C32' 1.3900 . ?
C31' H31' 0.9300 . ?
C32' C33' 1.3900 . ?
C32' H32' 0.9300 . ?
C33' H33' 0.9300 . ?
C34' O3' 1.225(17) . ?
C34' O2' 1.30(2) . ?
O4' H4' 0.8200 . ?

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
C2 C1 C6 123.9(3) . . ?
C2 C1 F1 117.9(3) . . ?
C6 C1 F1 118.2(4) . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 C7 118.4(3) . . ?
C5 C4 C7 123.1(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 117.6(3) . . ?
C1 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
O1 C7 C4 120.6(3) . . ?
O1 C7 C8 120.4(3) . . ?
C4 C7 C8 119.0(3) . . ?
C7 C8 C9 113.8(2) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 109.2(2) . . ?
C10 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C9 114.3(2) . . ?
N2 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 C12 111.0(2) . . ?
N2 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C11 110.5(2) . . ?
N1 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N1 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
N1 C13 C14 110.2(2) . . ?
N1 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N1 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N2 C14 C13 111.69(19) . . ?
N2 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N1 C15 C16 111.1(2) . . ?
N1 C15 C22 111.1(2) . . ?
C16 C15 C22 110.5(2) . . ?
N1 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C22 C15 H15 108.0 . . ?
C17 C16 C21 118.7(3) . . ?
C17 C16 C15 122.7(3) . . ?
C21 C16 C15 118.5(3) . . ?
C16 C17 C18 121.0(4) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 118.4(5) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C20 C19 C18 121.6(6) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.3(5) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.0(4) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C27 C22 C23 117.5(3) . . ?
C27 C22 C15 122.3(3) . . ?
C23 C22 C15 120.2(3) . . ?
C24 C23 C22 121.3(3) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 119.8(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 121.5(3) . . ?
C22 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C13 N1 C12 106.97(18) . . ?
C13 N1 C15 111.81(19) . . ?
C12 N1 C15 109.77(19) . . ?
C11 N2 C14 109.70(18) . . ?
C11 N2 C10 113.77(19) . . ?
C14 N2 C10 110.31(19) . . ?
C11 N2 H2A 108.9 . . ?
C14 N2 H2A 110.8 . . ?
C10 N2 H2A 103.1 . . ?
C29 C28 C33 120.0 . . ?
C29 C28 C34 125.1(9) . . ?
C33 C28 C34 114.9(9) . . ?
O4 C29 C28 118.2(9) . . ?
O4 C29 C30 121.7(9) . . ?
C28 C29 C30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C28 120.0 . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
O3 C34 O2 126.9(13) . . ?
O3 C34 C28 113.4(12) . . ?
O2 C34 C28 119.7(10) . . ?
C29 O4 H4 109.5 . . ?
C29' C28' C33' 120.0 . . ?
C29' C28' C34' 124.2(19) . . ?
C33' C28' C34' 115.4(19) . . ?
C28' C29' C30' 120.0 . . ?
C28' C29' O4' 115.5(16) . . ?
C30' C29' O4' 124.3(16) . . ?
C31' C30' C29' 120.0 . . ?
C31' C30' H30' 120.0 . . ?
C29' C30' H30' 120.0 . . ?
C32' C31' C30' 120.0 . . ?
C32' C31' H31' 120.0 . . ?
C30' C31' H31' 120.0 . . ?
C33' C32' C31' 120.0 . . ?
C33' C32' H32' 120.0 . . ?
C31' C32' H32' 120.0 . . ?
C32' C33' C28' 120.0 . . ?
C32' C33' H33' 120.0 . . ?
C28' C33' H33' 120.0 . . ?
O3' C34' O2' 122.1(13) . . ?
O3' C34' C28' 118.2(17) . . ?
O2' C34' C28' 119.6(19) . . ?
C29' O4' H4' 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
C6 C1 C2 C3 -0.7(5) . . . . ?
F1 C1 C2 C3 -179.3(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C2 C3 C4 C7 179.7(3) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C7 C4 C5 C6 -179.0(3) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
F1 C1 C6 C5 180.0(3) . . . . ?
C4 C5 C6 C1 -1.6(5) . . . . ?
C3 C4 C7 O1 0.4(4) . . . . ?
C5 C4 C7 O1 -179.4(3) . . . . ?
C3 C4 C7 C8 -177.8(3) . . . . ?
C5 C4 C7 C8 2.5(4) . . . . ?
O1 C7 C8 C9 -2.8(4) . . . . ?
C4 C7 C8 C9 175.4(2) . . . . ?
C7 C8 C9 C10 -176.9(2) . . . . ?
C8 C9 C10 N2 -165.9(2) . . . . ?
N2 C11 C12 N1 60.0(3) . . . . ?
N1 C13 C14 N2 -58.9(2) . . . . ?
N1 C15 C16 C17 -31.2(3) . . . . ?
C22 C15 C16 C17 92.6(3) . . . . ?
N1 C15 C16 C21 151.4(2) . . . . ?
C22 C15 C16 C21 -84.7(3) . . . . ?
C21 C16 C17 C18 0.1(4) . . . . ?
C15 C16 C17 C18 -177.2(3) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C18 C19 C20 -0.3(7) . . . . ?
C18 C19 C20 C21 -0.7(8) . . . . ?
C19 C20 C21 C16 1.4(6) . . . . ?
C17 C16 C21 C20 -1.1(4) . . . . ?
C15 C16 C21 C20 176.4(3) . . . . ?
N1 C15 C22 C27 69.8(3) . . . . ?
C16 C15 C22 C27 -54.0(3) . . . . ?
N1 C15 C22 C23 -111.4(3) . . . . ?
C16 C15 C22 C23 124.8(3) . . . . ?
C27 C22 C23 C24 -0.7(4) . . . . ?
C15 C22 C23 C24 -179.5(3) . . . . ?
C22 C23 C24 C25 1.0(5) . . . . ?
C23 C24 C25 C26 -1.1(5) . . . . ?
C24 C25 C26 C27 1.1(5) . . . . ?
C23 C22 C27 C26 0.6(4) . . . . ?
C15 C22 C27 C26 179.5(2) . . . . ?
C25 C26 C27 C22 -0.8(4) . . . . ?
C14 C13 N1 C12 62.0(2) . . . . ?
C14 C13 N1 C15 -177.84(18) . . . . ?
C11 C12 N1 C13 -62.9(3) . . . . ?
C11 C12 N1 C15 175.6(2) . . . . ?
C16 C15 N1 C13 174.4(2) . . . . ?
C22 C15 N1 C13 50.9(3) . . . . ?
C16 C15 N1 C12 -67.0(2) . . . . ?
C22 C15 N1 C12 169.5(2) . . . . ?
C12 C11 N2 C14 -53.7(3) . . . . ?
C12 C11 N2 C10 -177.77(19) . . . . ?
C13 C14 N2 C11 53.3(3) . . . . ?
C13 C14 N2 C10 179.4(2) . . . . ?
C9 C10 N2 C11 -58.3(3) . . . . ?
C9 C10 N2 C14 177.9(2) . . . . ?
C33 C28 C29 O4 -175.9(12) . . . . ?
C34 C28 C29 O4 1.6(9) . . . . ?
C33 C28 C29 C30 0.0 . . . . ?
C34 C28 C29 C30 177.5(12) . . . . ?
O4 C29 C30 C31 175.7(12) . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C28 0.0 . . . . ?
C29 C28 C33 C32 0.0 . . . . ?
C34 C28 C33 C32 -177.7(10) . . . . ?
C29 C28 C34 O3 4.7(11) . . . . ?
C33 C28 C34 O3 -177.7(7) . . . . ?
C29 C28 C34 O2 -178.4(6) . . . . ?
C33 C28 C34 O2 -0.9(12) . . . . ?
C33' C28' C29' C30' 0.0 . . . . ?
C34' C28' C29' C30' -172.4(17) . . . . ?
C33' C28' C29' O4' 175.4(14) . . . . ?
C34' C28' C29' O4' 3.0(13) . . . . ?
C28' C29' C30' C31' 0.0 . . . . ?
O4' C29' C30' C31' -175.0(16) . . . . ?
C29' C30' C31' C32' 0.0 . . . . ?
C30' C31' C32' C33' 0.0 . . . . ?
C31' C32' C33' C28' 0.0 . . . . ?
C29' C28' C33' C32' 0.0 . . . . ?
C34' C28' C33' C32' 173.0(16) . . . . ?
C29' C28' C34' O3' -10.2(17) . . . . ?
C33' C28' C34' O3' 177.1(9) . . . . ?
C29' C28' C34' O2' 173.1(9) . . . . ?
C33' C28' C34' O2' 0.5(16) . . . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6

