# Electronic Supplementary Material (ESI) for ChemComm.
# 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_huahl_0328_1
_database_code_depnum_ccdc_archive 'CCDC 1485325'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;
_audit_creation_date             2016-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C29 H28 F4 N2 O5'
_chemical_formula_sum            'C29 H28 F4 N2 O5'
_chemical_formula_weight         560.53
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.4966(6)
_cell_length_b                   9.7777(4)
_cell_length_c                   22.6334(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.263(4)
_cell_angle_gamma                90.00
_cell_volume                     2721.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1938
_cell_measurement_temperature    290.83(10)
_cell_measurement_theta_max      22.7930
_cell_measurement_theta_min      3.7370
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10898
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.31
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.83(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00   31.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -120.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega   37.00   63.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   50.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000 -150.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0075893000
_diffrn_orient_matrix_UB_12      0.0130062000
_diffrn_orient_matrix_UB_13      0.0313091000
_diffrn_orient_matrix_UB_21      -0.0364329000
_diffrn_orient_matrix_UB_22      0.0560917000
_diffrn_orient_matrix_UB_23      -0.0053835000
_diffrn_orient_matrix_UB_31      -0.0440698000
_diffrn_orient_matrix_UB_32      -0.0440969000
_diffrn_orient_matrix_UB_33      0.0023952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3083
_reflns_number_total             5349
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.027
_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)+(0.0534P)²+1.0598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1605
_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    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C16(H16A,H16B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C29(H29A,H29B,H29C)
;
_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
F1 F 0.48026(14) 0.56692(19) 0.17009(8) 0.0672(5) Uani 1 d . . .
F2 F 0.43014(13) 0.5537(2) 0.07319(8) 0.0717(6) Uani 1 d . . .
F3 F 0.74710(16) 0.4724(2) 0.45594(8) 0.0799(6) Uani 1 d . . .
F4 F 0.76160(17) 0.2537(2) 0.46661(8) 0.0852(6) Uani 1 d . . .
O1 O 0.5791(2) 0.7755(2) 0.12339(12) 0.0808(8) Uani 1 d . . .
O2 O 0.66010(16) 0.6219(2) 0.07260(9) 0.0546(5) Uani 1 d . . .
O3 O 0.70483(17) 0.6044(2) 0.22054(10) 0.0601(6) Uani 1 d . . .
O4 O 0.92460(18) 0.4645(3) 0.39707(11) 0.0758(7) Uani 1 d . . .
O5 O 0.9696(2) 0.3204(3) 0.47442(12) 0.0943(9) Uani 1 d . . .
N1 N 0.68583(18) 0.1473(2) 0.22603(10) 0.0444(6) Uani 1 d . . .
N2 N 0.65594(19) 0.5443(2) 0.30914(11) 0.0499(6) Uani 1 d . . .
C1 C 0.6382(2) 0.1906(3) 0.16938(13) 0.0442(7) Uani 1 d . . .
C2 C 0.6140(2) 0.1151(3) 0.11634(14) 0.0540(8) Uani 1 d . . .
H2 H 0.6288 0.0220 0.1157 0.065 Uiso 1 calc . . R
C3 C 0.5672(3) 0.1837(4) 0.06495(14) 0.0617(9) Uani 1 d . . .
H3 H 0.5533 0.1371 0.0286 0.074 Uiso 1 calc . . R
C4 C 0.5406(2) 0.3216(3) 0.06666(14) 0.0560(8) Uani 1 d . . .
H4 H 0.5071 0.3643 0.0315 0.067 Uiso 1 calc . . R
C5 C 0.5622(2) 0.3971(3) 0.11897(12) 0.0443(7) Uani 1 d . . .
C6 C 0.6169(2) 0.3322(3) 0.17146(12) 0.0403(6) Uani 1 d . . .
C7 C 0.6562(2) 0.3736(3) 0.23255(12) 0.0402(6) Uani 1 d . . .
C8 C 0.6960(2) 0.2584(3) 0.26411(12) 0.0431(7) Uani 1 d . . .
C9 C 0.7518(2) 0.2531(3) 0.32742(12) 0.0426(7) Uani 1 d . . .
C10 C 0.7189(2) 0.3395(3) 0.36694(13) 0.0470(7) Uani 1 d . . .
C11 C 0.6244(2) 0.4343(3) 0.34623(13) 0.0498(7) Uani 1 d . . .
H11A H 0.5646 0.3830 0.3233 0.060 Uiso 1 calc . . R
H11B H 0.5997 0.4732 0.3809 0.060 Uiso 1 calc . . R
C12 C 0.6740(2) 0.5166(3) 0.25283(13) 0.0452(7) Uani 1 d . . .
C13 C 0.6804(3) 0.6805(3) 0.33447(15) 0.0716(10) Uani 1 d . . .
H13A H 0.6359 0.6984 0.3641 0.107 Uiso 1 calc . . GR
H13B H 0.6656 0.7476 0.3031 0.107 Uiso 1 calc . . GR
H13C H 0.7557 0.6851 0.3529 0.107 Uiso 1 calc . . GR
C14 C 0.5198(2) 0.5404(3) 0.11887(13) 0.0518(8) Uani 1 d . . .
C15 C 0.5916(2) 0.6610(3) 0.10747(13) 0.0517(7) Uani 1 d . . .
C16 C 0.7275(3) 0.7292(4) 0.05342(17) 0.0752(10) Uani 1 d . . .
H16A H 0.7836 0.7564 0.0867 0.090 Uiso 1 calc . . R
H16B H 0.6834 0.8086 0.0400 0.090 Uiso 1 calc . . R
C17 C 0.7772(3) 0.6751(4) 0.00407(16) 0.0825(11) Uani 1 d . . .
H17A H 0.7211 0.6485 -0.0286 0.124 Uiso 1 calc . . GR
H17B H 0.8212 0.5970 0.0179 0.124 Uiso 1 calc . . GR
H17C H 0.8218 0.7444 -0.0093 0.124 Uiso 1 calc . . GR
C18 C 0.8486(2) 0.1616(3) 0.34237(13) 0.0449(7) Uani 1 d . . .
C19 C 0.8564(2) 0.0590(3) 0.38498(15) 0.0593(8) Uani 1 d . . .
H19 H 0.7999 0.0461 0.4061 0.071 Uiso 1 calc . . R
C20 C 0.9472(3) -0.0251(3) 0.39670(15) 0.0659(9) Uani 1 d . . .
H20 H 0.9506 -0.0929 0.4258 0.079 Uiso 1 calc . . R
C21 C 1.0326(2) -0.0102(3) 0.36607(16) 0.0598(9) Uani 1 d . . .
C22 C 1.0253(2) 0.0923(3) 0.32370(15) 0.0600(9) Uani 1 d . . .
H22 H 1.0824 0.1052 0.3030 0.072 Uiso 1 calc . . R
C23 C 0.9348(2) 0.1766(3) 0.31126(13) 0.0523(8) Uani 1 d . . .
H23 H 0.9316 0.2438 0.2819 0.063 Uiso 1 calc . . R
C24 C 1.1312(3) -0.1026(4) 0.3778(2) 0.0870(13) Uani 1 d . . .
H24A H 1.1323 -0.1597 0.3434 0.131 Uiso 1 calc . . GR
H24B H 1.1279 -0.1588 0.4122 0.131 Uiso 1 calc . . GR
H24C H 1.1960 -0.0479 0.3853 0.131 Uiso 1 calc . . GR
C25 C 0.6997(3) 0.0027(3) 0.24234(14) 0.0570(8) Uani 1 d . . .
H25A H 0.7747 -0.0225 0.2450 0.086 Uiso 1 calc . . GR
H25B H 0.6555 -0.0522 0.2123 0.086 Uiso 1 calc . . GR
H25C H 0.6780 -0.0122 0.2804 0.086 Uiso 1 calc . . GR
C26 C 0.7814(3) 0.3571(3) 0.43022(13) 0.0556(8) Uani 1 d . . .
C27 C 0.9049(3) 0.3754(4) 0.43672(15) 0.0622(9) Uani 1 d . . .
C28 C 1.0386(3) 0.5008(6) 0.3972(2) 0.1155(17) Uani 1 d . . .
H28A H 1.0595 0.5765 0.4245 0.139 Uiso 1 calc . . R
H28B H 1.0850 0.4235 0.4110 0.139 Uiso 1 calc . . R
C29 C 1.0522(5) 0.5374(7) 0.3398(2) 0.153(3) Uani 1 d . . .
H29A H 1.0395 0.4593 0.3138 0.230 Uiso 1 calc . . GR
H29B H 1.1251 0.5699 0.3410 0.230 Uiso 1 calc . . GR
H29C H 1.0016 0.6084 0.3249 0.230 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.363(3) . ?
F2 C14 1.389(3) . ?
F3 C26 1.372(3) . ?
F4 C26 1.354(3) . ?
O1 C15 1.195(3) . ?
O2 C15 1.320(3) . ?
O2 C16 1.459(4) . ?
O3 C12 1.232(3) . ?
O4 C27 1.305(4) . ?
O4 C28 1.468(4) . ?
O5 C27 1.193(4) . ?
N1 C1 1.380(3) . ?
N1 C8 1.378(3) . ?
N1 C25 1.464(3) . ?
N2 C11 1.461(3) . ?
N2 C12 1.361(3) . ?
N2 C13 1.461(4) . ?
C1 C2 1.396(4) . ?
C1 C6 1.412(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 C6 1.412(4) . ?
C5 C14 1.498(4) . ?
C6 C7 1.440(4) . ?
C7 C8 1.378(4) . ?
C7 C12 1.477(4) . ?
C8 C9 1.479(4) . ?
C9 C10 1.347(4) . ?
C9 C18 1.494(4) . ?
C10 C11 1.509(4) . ?
C10 C26 1.514(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.531(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.470(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.383(4) . ?
C18 C23 1.396(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(4) . ?
C21 C22 1.379(4) . ?
C21 C24 1.512(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(4) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.535(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.386(6) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C15 O2 C16 116.1(2) . . ?
C27 O4 C28 117.5(3) . . ?
C1 N1 C25 122.9(2) . . ?
C8 N1 C1 108.4(2) . . ?
C8 N1 C25 127.6(2) . . ?
C11 N2 C13 120.3(2) . . ?
C12 N2 C11 119.9(2) . . ?
C12 N2 C13 119.4(2) . . ?
N1 C1 C2 128.9(3) . . ?
N1 C1 C6 108.8(2) . . ?
C2 C1 C6 122.3(3) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.5(3) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.1(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 C14 118.9(3) . . ?
C6 C5 C14 122.7(3) . . ?
C1 C6 C7 105.8(2) . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 135.5(3) . . ?
C6 C7 C12 124.8(2) . . ?
C8 C7 C6 107.3(2) . . ?
C8 C7 C12 126.3(3) . . ?
N1 C8 C7 109.6(2) . . ?
N1 C8 C9 123.6(2) . . ?
C7 C8 C9 126.5(3) . . ?
C8 C9 C18 117.6(2) . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 C18 123.8(3) . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 C26 122.1(3) . . ?
C11 C10 C26 117.9(3) . . ?
N2 C11 C10 110.7(2) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O3 C12 N2 122.6(3) . . ?
O3 C12 C7 121.4(3) . . ?
N2 C12 C7 116.0(2) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F1 C14 F2 104.4(2) . . ?
F1 C14 C5 111.0(2) . . ?
F1 C14 C15 108.0(2) . . ?
F2 C14 C5 109.1(2) . . ?
F2 C14 C15 102.8(2) . . ?
C5 C14 C15 120.2(2) . . ?
O1 C15 O2 125.8(3) . . ?
O1 C15 C14 124.0(3) . . ?
O2 C15 C14 109.9(3) . . ?
O2 C16 H16A 110.1 . . ?
O2 C16 H16B 110.1 . . ?
O2 C16 C17 108.2(3) . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 H16A 110.1 . . ?
C17 C16 H16B 110.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C9 123.1(3) . . ?
C19 C18 C23 117.5(3) . . ?
C23 C18 C9 119.3(3) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.1(3) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C24 121.8(3) . . ?
C22 C21 C20 117.7(3) . . ?
C22 C21 C24 120.5(3) . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.6(3) . . ?
C23 C22 H22 119.2 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F3 C26 C10 110.3(2) . . ?
F3 C26 C27 104.4(3) . . ?
F4 C26 F3 104.5(2) . . ?
F4 C26 C10 111.8(3) . . ?
F4 C26 C27 108.5(3) . . ?
C10 C26 C27 116.4(2) . . ?
O4 C27 C26 108.7(3) . . ?
O5 C27 O4 127.3(3) . . ?
O5 C27 C26 123.9(3) . . ?
O4 C28 H28A 109.7 . . ?
O4 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C29 C28 O4 110.0(4) . . ?
C29 C28 H28A 109.7 . . ?
C29 C28 H28B 109.7 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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 C14 C15 O1 -28.4(4) . . . . ?
F1 C14 C15 O2 158.1(2) . . . . ?
F2 C14 C15 O1 81.6(4) . . . . ?
F2 C14 C15 O2 -91.9(3) . . . . ?
F3 C26 C27 O4 -75.8(3) . . . . ?
F3 C26 C27 O5 100.9(4) . . . . ?
F4 C26 C27 O4 173.2(3) . . . . ?
F4 C26 C27 O5 -10.2(4) . . . . ?
N1 C1 C2 C3 -179.1(3) . . . . ?
N1 C1 C6 C5 -176.4(2) . . . . ?
N1 C1 C6 C7 1.0(3) . . . . ?
N1 C8 C9 C10 -151.1(3) . . . . ?
N1 C8 C9 C18 34.7(4) . . . . ?
C1 N1 C8 C7 -0.5(3) . . . . ?
C1 N1 C8 C9 -174.8(2) . . . . ?
C1 C2 C3 C4 -3.0(4) . . . . ?
C1 C6 C7 C8 -1.3(3) . . . . ?
C1 C6 C7 C12 165.4(2) . . . . ?
C2 C1 C6 C5 4.7(4) . . . . ?
C2 C1 C6 C7 -178.0(2) . . . . ?
C2 C3 C4 C5 1.9(5) . . . . ?
C3 C4 C5 C6 2.5(4) . . . . ?
C3 C4 C5 C14 -173.1(3) . . . . ?
C4 C5 C6 C1 -5.6(4) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C4 C5 C14 F1 138.5(3) . . . . ?
C4 C5 C14 F2 24.0(3) . . . . ?
C4 C5 C14 C15 -94.2(3) . . . . ?
C5 C6 C7 C8 175.4(3) . . . . ?
C5 C6 C7 C12 -17.9(5) . . . . ?
C5 C14 C15 O1 -157.1(3) . . . . ?
C5 C14 C15 O2 29.5(4) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C5 C14 F1 -36.8(4) . . . . ?
C6 C5 C14 F2 -151.3(2) . . . . ?
C6 C5 C14 C15 90.5(3) . . . . ?
C6 C7 C8 N1 1.1(3) . . . . ?
C6 C7 C8 C9 175.2(2) . . . . ?
C6 C7 C12 O3 -33.8(4) . . . . ?
C6 C7 C12 N2 147.1(3) . . . . ?
C7 C8 C9 C10 35.6(4) . . . . ?
C7 C8 C9 C18 -138.6(3) . . . . ?
C8 N1 C1 C2 178.5(3) . . . . ?
C8 N1 C1 C6 -0.4(3) . . . . ?
C8 C7 C12 O3 130.4(3) . . . . ?
C8 C7 C12 N2 -48.7(4) . . . . ?
C8 C9 C10 C11 2.2(4) . . . . ?
C8 C9 C10 C26 -170.5(3) . . . . ?
C8 C9 C18 C19 -123.6(3) . . . . ?
C8 C9 C18 C23 54.8(4) . . . . ?
C9 C10 C11 N2 -72.8(3) . . . . ?
C9 C10 C26 F3 165.2(3) . . . . ?
C9 C10 C26 F4 -78.9(3) . . . . ?
C9 C10 C26 C27 46.6(4) . . . . ?
C9 C18 C19 C20 179.0(3) . . . . ?
C9 C18 C23 C22 -179.4(3) . . . . ?
C10 C9 C18 C19 62.6(4) . . . . ?
C10 C9 C18 C23 -119.0(3) . . . . ?
C10 C26 C27 O4 46.0(4) . . . . ?
C10 C26 C27 O5 -137.3(3) . . . . ?
C11 N2 C12 O3 -177.2(3) . . . . ?
C11 N2 C12 C7 1.9(4) . . . . ?
C11 C10 C26 F3 -7.7(4) . . . . ?
C11 C10 C26 F4 108.2(3) . . . . ?
C11 C10 C26 C27 -126.3(3) . . . . ?
C12 N2 C11 C10 71.3(3) . . . . ?
C12 C7 C8 N1 -165.3(2) . . . . ?
C12 C7 C8 C9 8.8(4) . . . . ?
C13 N2 C11 C10 -101.6(3) . . . . ?
C13 N2 C12 O3 -4.2(4) . . . . ?
C13 N2 C12 C7 174.9(3) . . . . ?
C14 C5 C6 C1 169.8(2) . . . . ?
C14 C5 C6 C7 -6.6(5) . . . . ?
C15 O2 C16 C17 -166.1(3) . . . . ?
C16 O2 C15 O1 1.5(5) . . . . ?
C16 O2 C15 C14 174.8(3) . . . . ?
C18 C9 C10 C11 176.0(3) . . . . ?
C18 C9 C10 C26 3.3(4) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C19 C18 C23 C22 -0.9(4) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C19 C20 C21 C24 -179.1(3) . . . . ?
C20 C21 C22 C23 -1.0(5) . . . . ?
C21 C22 C23 C18 1.2(5) . . . . ?
C23 C18 C19 C20 0.5(5) . . . . ?
C24 C21 C22 C23 178.7(3) . . . . ?
C25 N1 C1 C2 -12.9(4) . . . . ?
C25 N1 C1 C6 168.1(2) . . . . ?
C25 N1 C8 C7 -168.3(2) . . . . ?
C25 N1 C8 C9 17.4(4) . . . . ?
C26 C10 C11 N2 100.3(3) . . . . ?
C27 O4 C28 C29 150.9(5) . . . . ?
C28 O4 C27 O5 1.3(5) . . . . ?
C28 O4 C27 C26 177.8(3) . . . . ?

_olex2_date_sample_data_collection 2016-03-28
_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_131_1
_database_code_depnum_ccdc_archive 'CCDC 1485326'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;
_audit_creation_date             2015-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H22 F2 N2 O3'
_chemical_formula_sum            'C24 H22 F2 N2 O3'
_chemical_formula_weight         424.44
_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 0.0181 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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   12.2175(2)
_cell_length_b                   15.8782(3)
_cell_length_c                   22.0697(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4281.35(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3446
_cell_measurement_temperature    291.48(10)
_cell_measurement_theta_max      68.9050
_cell_measurement_theta_min      4.0030
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9673
_diffrn_reflns_theta_full        69.71
_diffrn_reflns_theta_max         69.71
_diffrn_reflns_theta_min         4.01
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.48(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   24.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega   93.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
  4 omega   58.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   52.00  131.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   90.0000 79

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
  9 omega   30.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega   23.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega  -21.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega  -67.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 13 omega  -39.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  108.0000 -169.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0961398000
_diffrn_orient_matrix_UB_12      0.0417521000
_diffrn_orient_matrix_UB_13      0.0337526000
_diffrn_orient_matrix_UB_21      0.0759136000
_diffrn_orient_matrix_UB_22      0.0723460000
_diffrn_orient_matrix_UB_23      0.0199654000
_diffrn_orient_matrix_UB_31      -0.0298630000
_diffrn_orient_matrix_UB_32      0.0493881000
_diffrn_orient_matrix_UB_33      -0.0577413000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3110
_reflns_number_total             3993
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0711P)²+0.8709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1408
_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    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C)
;
_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
F1 F 0.20032(12) -0.21729(13) 0.58752(9) 0.1185(7) Uani 1 d . . .
F2 F 0.20248(11) -0.08087(12) 0.59326(8) 0.1090(6) Uani 1 d . . .
O1 O 0.62678(11) 0.03385(8) 0.60559(6) 0.0573(3) Uani 1 d . . .
O2 O 0.1761(2) -0.19635(18) 0.70626(13) 0.1497(11) Uani 1 d . . .
O3 O 0.30418(16) -0.09592(11) 0.70608(7) 0.0829(5) Uani 1 d . . .
N1 N 0.64229(12) -0.24962(9) 0.59066(7) 0.0508(4) Uani 1 d . . .
N2 N 0.46283(12) -0.01461(9) 0.57278(6) 0.0489(4) Uani 1 d . . .
C1 C 0.74183(14) -0.21466(11) 0.57603(8) 0.0488(4) Uani 1 d . . .
C2 C 0.84359(16) -0.25381(14) 0.56806(10) 0.0645(5) Uani 1 d . . .
H2 H 0.8520 -0.3116 0.5730 0.077 Uiso 1 calc . . R
C3 C 0.92976(17) -0.20351(16) 0.55274(11) 0.0745(6) Uani 1 d . . .
H3 H 0.9984 -0.2277 0.5472 0.089 Uiso 1 calc . . R
C4 C 0.91772(16) -0.11663(15) 0.54511(11) 0.0720(6) Uani 1 d . . .
H4 H 0.9781 -0.0844 0.5342 0.086 Uiso 1 calc . . R
C5 C 0.81848(14) -0.07797(13) 0.55350(9) 0.0576(5) Uani 1 d . . .
H5 H 0.8112 -0.0201 0.5485 0.069 Uiso 1 calc . . R
C6 C 0.72818(13) -0.12749(11) 0.56981(7) 0.0444(4) Uani 1 d . . .
C7 C 0.61486(13) -0.11033(10) 0.58091(7) 0.0411(4) Uani 1 d . . .
C8 C 0.56455(13) -0.18663(10) 0.59355(7) 0.0431(4) Uani 1 d . . .
C9 C 0.45057(13) -0.20093(11) 0.61211(7) 0.0464(4) Uani 1 d . . .
C10 C 0.37273(14) -0.14990(13) 0.58949(8) 0.0515(4) Uani 1 d . . .
C11 C 0.40259(14) -0.08294(12) 0.54446(8) 0.0529(4) Uani 1 d . . .
H11A H 0.4469 -0.1076 0.5126 0.063 Uiso 1 calc . . R
H11B H 0.3364 -0.0608 0.5261 0.063 Uiso 1 calc . . R
C12 C 0.56946(14) -0.02504(10) 0.58756(7) 0.0439(4) Uani 1 d . . .
C13 C 0.6262(2) -0.34054(12) 0.59474(14) 0.0824(7) Uani 1 d . . .
H13A H 0.6418 -0.3591 0.6352 0.124 Uiso 1 calc . . GR
H13B H 0.6744 -0.3684 0.5669 0.124 Uiso 1 calc . . GR
H13C H 0.5517 -0.3540 0.5848 0.124 Uiso 1 calc . . GR
C14 C 0.40708(18) 0.06375(14) 0.58835(10) 0.0685(6) Uani 1 d . . .
H14A H 0.3580 0.0540 0.6216 0.103 Uiso 1 calc . . GR
H14B H 0.3664 0.0835 0.5539 0.103 Uiso 1 calc . . GR
H14C H 0.4602 0.1054 0.5998 0.103 Uiso 1 calc . . GR
C15 C 0.25666(16) -0.15170(17) 0.61246(12) 0.0758(7) Uani 1 d . . .
C16 C 0.2402(2) -0.15306(19) 0.68107(13) 0.0883(8) Uani 1 d . . .
C17 C 0.3028(4) -0.0881(2) 0.77219(13) 0.1213(13) Uani 1 d . . .
H17A H 0.3137 -0.1427 0.7909 0.146 Uiso 1 calc . . R
H17B H 0.2332 -0.0656 0.7857 0.146 Uiso 1 calc . . R
C18 C 0.3926(5) -0.0304(3) 0.78870(16) 0.162(2) Uani 1 d . . .
H18A H 0.4597 -0.0502 0.7712 0.243 Uiso 1 calc . . GR
H18B H 0.3997 -0.0285 0.8320 0.243 Uiso 1 calc . . GR
H18C H 0.3767 0.0250 0.7737 0.243 Uiso 1 calc . . GR
C19 C 0.42828(15) -0.26453(12) 0.66031(8) 0.0530(4) Uani 1 d . . .
C20 C 0.3589(2) -0.33237(15) 0.65151(11) 0.0778(7) Uani 1 d . . .
H20 H 0.3262 -0.3408 0.6139 0.093 Uiso 1 calc . . R
C21 C 0.3382(2) -0.38758(18) 0.69848(13) 0.0974(10) Uani 1 d . . .
H21 H 0.2922 -0.4334 0.6921 0.117 Uiso 1 calc . . R
C22 C 0.3848(2) -0.37558(18) 0.75440(12) 0.0937(9) Uani 1 d . . .
H22 H 0.3683 -0.4118 0.7863 0.112 Uiso 1 calc . . R
C23 C 0.4559(2) -0.30974(16) 0.76289(10) 0.0812(7) Uani 1 d . . .
H23 H 0.4888 -0.3018 0.8004 0.097 Uiso 1 calc . . R
C24 C 0.47866(16) -0.25511(13) 0.71577(9) 0.0611(5) Uani 1 d . . .
H24 H 0.5285 -0.2116 0.7216 0.073 Uiso 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
F1 C15 1.364(3) . ?
F2 C15 1.372(3) . ?
O1 C12 1.234(2) . ?
O2 C16 1.181(3) . ?
O3 C16 1.318(3) . ?
O3 C17 1.465(3) . ?
N1 C1 1.375(2) . ?
N1 C8 1.381(2) . ?
N1 C13 1.460(2) . ?
N2 C11 1.452(2) . ?
N2 C12 1.353(2) . ?
N2 C14 1.459(2) . ?
C1 C2 1.401(3) . ?
C1 C6 1.401(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(2) . ?
C6 C7 1.432(2) . ?
C7 C8 1.387(2) . ?
C7 C12 1.471(2) . ?
C8 C9 1.469(2) . ?
C9 C10 1.345(3) . ?
C9 C19 1.492(2) . ?
C10 C11 1.500(2) . ?
C10 C15 1.506(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.528(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.474(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.384(3) . ?
C19 C24 1.378(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.372(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(3) . ?
C24 H24 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
C16 O3 C17 118.0(2) . . ?
C1 N1 C8 109.06(14) . . ?
C1 N1 C13 122.20(17) . . ?
C8 N1 C13 128.38(17) . . ?
C11 N2 C14 120.11(15) . . ?
C12 N2 C11 120.01(14) . . ?
C12 N2 C14 119.80(16) . . ?
N1 C1 C2 129.42(17) . . ?
N1 C1 C6 108.46(15) . . ?
C6 C1 C2 122.12(17) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.14(19) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.77(19) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.64(19) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 119.06(16) . . ?
C1 C6 C7 106.63(15) . . ?
C5 C6 C7 134.27(17) . . ?
C6 C7 C12 123.83(15) . . ?
C8 C7 C6 107.26(14) . . ?
C8 C7 C12 128.11(15) . . ?
N1 C8 C7 108.58(14) . . ?
N1 C8 C9 123.57(15) . . ?
C7 C8 C9 127.67(16) . . ?
C8 C9 C19 118.46(15) . . ?
C10 C9 C8 118.26(15) . . ?
C10 C9 C19 122.90(16) . . ?
C9 C10 C11 120.04(16) . . ?
C9 C10 C15 121.96(17) . . ?
C11 C10 C15 117.72(17) . . ?
N2 C11 C10 111.56(14) . . ?
N2 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O1 C12 N2 122.10(16) . . ?
O1 C12 C7 121.05(15) . . ?
N2 C12 C7 116.85(15) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 C15 F2 104.93(18) . . ?
F1 C15 C10 110.7(2) . . ?
F1 C15 C16 108.8(2) . . ?
F2 C15 C10 109.57(18) . . ?
F2 C15 C16 104.7(2) . . ?
C10 C15 C16 117.23(18) . . ?
O2 C16 O3 126.6(3) . . ?
O2 C16 C15 124.2(3) . . ?
O3 C16 C15 109.11(19) . . ?
O3 C17 H17A 110.3 . . ?
O3 C17 H17B 110.3 . . ?
O3 C17 C18 106.9(3) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C9 122.59(17) . . ?
C24 C19 C9 118.57(16) . . ?
C24 C19 C20 118.84(18) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 120.67(19) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?

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 C15 C16 O2 -10.3(4) . . . . ?
F1 C15 C16 O3 172.92(19) . . . . ?
F2 C15 C16 O2 101.5(3) . . . . ?
F2 C15 C16 O3 -75.3(2) . . . . ?
N1 C1 C2 C3 179.2(2) . . . . ?
N1 C1 C6 C5 -178.55(16) . . . . ?
N1 C1 C6 C7 -0.41(19) . . . . ?
N1 C8 C9 C10 -151.27(18) . . . . ?
N1 C8 C9 C19 35.6(2) . . . . ?
C1 N1 C8 C7 -0.28(19) . . . . ?
C1 N1 C8 C9 -175.73(15) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C6 C7 C8 0.24(19) . . . . ?
C1 C6 C7 C12 170.72(15) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
C2 C1 C6 C7 179.89(17) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C5 C6 C7 C8 177.96(19) . . . . ?
C5 C6 C7 C12 -11.5(3) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C6 C7 C8 N1 0.02(19) . . . . ?
C6 C7 C8 C9 175.23(15) . . . . ?
C6 C7 C12 O1 -26.6(2) . . . . ?
C6 C7 C12 N2 153.17(16) . . . . ?
C7 C8 C9 C10 34.2(3) . . . . ?
C7 C8 C9 C19 -138.91(18) . . . . ?
C8 N1 C1 C2 -179.89(19) . . . . ?
C8 N1 C1 C6 0.4(2) . . . . ?
C8 C7 C12 O1 141.87(18) . . . . ?
C8 C7 C12 N2 -38.4(2) . . . . ?
C8 C9 C10 C11 2.6(3) . . . . ?
C8 C9 C10 C15 -171.20(18) . . . . ?
C8 C9 C19 C20 -123.1(2) . . . . ?
C8 C9 C19 C24 57.0(3) . . . . ?
C9 C10 C11 N2 -71.8(2) . . . . ?
C9 C10 C15 F1 -79.8(2) . . . . ?
C9 C10 C15 F2 164.94(19) . . . . ?
C9 C10 C15 C16 45.8(3) . . . . ?
C9 C19 C20 C21 -177.7(2) . . . . ?
C9 C19 C24 C23 176.4(2) . . . . ?
C10 C9 C19 C20 64.1(3) . . . . ?
C10 C9 C19 C24 -115.7(2) . . . . ?
C10 C15 C16 O2 -136.9(3) . . . . ?
C10 C15 C16 O3 46.4(3) . . . . ?
C11 N2 C12 O1 172.04(15) . . . . ?
C11 N2 C12 C7 -7.7(2) . . . . ?
C11 C10 C15 F1 106.3(2) . . . . ?
C11 C10 C15 F2 -9.0(3) . . . . ?
C11 C10 C15 C16 -128.1(2) . . . . ?
C12 N2 C11 C10 75.9(2) . . . . ?
C12 C7 C8 N1 -169.93(16) . . . . ?
C12 C7 C8 C9 5.3(3) . . . . ?
C13 N1 C1 C2 -6.2(3) . . . . ?
C13 N1 C1 C6 174.11(19) . . . . ?
C13 N1 C8 C7 -173.5(2) . . . . ?
C13 N1 C8 C9 11.1(3) . . . . ?
C14 N2 C11 C10 -100.77(19) . . . . ?
C14 N2 C12 O1 -11.3(2) . . . . ?
C14 N2 C12 C7 169.00(15) . . . . ?
C15 C10 C11 N2 102.3(2) . . . . ?
C16 O3 C17 C18 171.3(3) . . . . ?
C17 O3 C16 O2 4.7(4) . . . . ?
C17 O3 C16 C15 -178.7(2) . . . . ?
C19 C9 C10 C11 175.37(17) . . . . ?
C19 C9 C10 C15 1.6(3) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C19 C24 C23 -3.5(4) . . . . ?
C20 C21 C22 C23 -2.5(5) . . . . ?
C21 C22 C23 C24 1.2(5) . . . . ?
C22 C23 C24 C19 1.8(4) . . . . ?
C24 C19 C20 C21 2.2(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_huahl_0615
_database_code_depnum_ccdc_archive 'CCDC 1485755'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;
_audit_creation_date             2016-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H25 Cl F4 N2 O5'
_chemical_formula_sum            'C28 H25 Cl F4 N2 O5'
_chemical_formula_weight         580.95
_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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.8985(11)
_cell_length_b                   14.8772(11)
_cell_length_c                   27.961(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.992(8)
_cell_angle_gamma                90.00
_cell_volume                     5313.5(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    293.26(10)
_cell_measurement_theta_max      27.4660
_cell_measurement_theta_min      3.5840
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_unetI/netI     0.1213
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            20818
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.30
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.26(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00    1.60   1.0500   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.1930  -77.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   82.00   1.0500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7086   19.0000 -180.0000 120

#__ type_ start__ end____ width___ exp.time_
  3 omega   49.00   93.10   1.0500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7086  178.0000   30.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0221531000
_diffrn_orient_matrix_UB_12      -0.0271696000
_diffrn_orient_matrix_UB_13      -0.0168207000
_diffrn_orient_matrix_UB_21      0.0137264000
_diffrn_orient_matrix_UB_22      -0.0327953000
_diffrn_orient_matrix_UB_23      0.0181748000
_diffrn_orient_matrix_UB_31      -0.0490473000
_diffrn_orient_matrix_UB_32      -0.0214401000
_diffrn_orient_matrix_UB_33      -0.0065093000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5031
_reflns_number_total             10440
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         10440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.0888
_refine_ls_restrained_S_all      1.041
_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)+(0.0987P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2027
_refine_ls_wR_factor_ref         0.2627
_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    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B), C27(H27A,H27B), C39(H39A,H39B), C43(H43A,H43B),
 C54(H54A,H54B)
2.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C2(H2), C4(H4), C5(H5), C21(H21), C22(H22), C24(H24), C29(H29),
 C30(H30), C32(H32), C33(H33), C48(H48), C49(H49), C51(H51)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C28(H28A,H28B,
 H28C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C55(H55A,H55B,H55C), C59(H59A,
 H59B,H59C)
;
_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
Cl1 Cl 0.88564(13) 0.78642(11) 0.18180(6) 0.0702(5) Uani 1 d . . .
F1 F 1.0124(2) 1.1042(2) 0.35010(10) 0.0539(8) Uani 1 d . . .
F2 F 0.8922(3) 1.2025(2) 0.35919(13) 0.0737(10) Uani 1 d . . .
F3 F 0.5985(2) 0.55836(18) 0.47972(12) 0.0591(9) Uani 1 d . . .
F4 F 0.5340(2) 0.6267(2) 0.53802(12) 0.0613(9) Uani 1 d . . .
O1 O 0.7665(3) 1.1173(3) 0.28025(15) 0.0651(12) Uani 1 d . . .
O2 O 0.9321(3) 1.1152(2) 0.26356(13) 0.0494(9) Uani 1 d . . .
O3 O 0.5728(3) 1.0712(2) 0.43776(13) 0.0449(9) Uani 1 d . . .
O4 O 0.4231(3) 0.5669(2) 0.42481(14) 0.0535(10) Uani 1 d . . .
O5 O 0.3500(3) 0.6442(2) 0.48068(16) 0.0598(11) Uani 1 d . . .
N1 N 0.7609(3) 0.8272(2) 0.40200(14) 0.0354(9) Uani 1 d . . .
N2 N 0.7377(3) 1.1151(3) 0.43024(15) 0.0414(10) Uani 1 d . . .
C0AA C 0.7561(4) 0.8900(3) 0.28956(19) 0.0420(12) Uani 1 d . . .
H0AA H 0.6891 0.8951 0.2980 0.050 Uiso 1 calc . . R
C2 C 0.7694(4) 0.8478(4) 0.24754(19) 0.0469(14) Uani 1 d . . .
H2 H 0.7120 0.8250 0.2273 0.056 Uiso 1 calc . . R
C3 C 0.8689(4) 0.8395(3) 0.23537(19) 0.0466(14) Uani 1 d . . .
C4 C 0.9551(4) 0.8716(3) 0.2648(2) 0.0483(14) Uani 1 d . . .
H4 H 1.0219 0.8646 0.2564 0.058 Uiso 1 calc . . R
C5 C 0.9402(4) 0.9150(3) 0.30746(19) 0.0410(12) Uani 1 d . . .
H5 H 0.9977 0.9371 0.3278 0.049 Uiso 1 calc . . R
C6 C 0.8405(4) 0.9256(3) 0.32008(18) 0.0381(12) Uani 1 d . . .
C7 C 0.8251(4) 0.9686(3) 0.36644(17) 0.0370(11) Uani 1 d . . .
C8 C 0.8589(4) 1.0538(3) 0.37883(18) 0.0395(12) Uani 1 d . . .
C9 C 0.8456(4) 1.0896(3) 0.42785(18) 0.0409(12) Uani 1 d . . .
H9A H 0.8669 1.0440 0.4520 0.049 Uiso 1 calc . . R
H9B H 0.8906 1.1415 0.4351 0.049 Uiso 1 calc . . R
C10 C 0.6640(4) 1.0518(3) 0.43240(17) 0.0333(11) Uani 1 d . . .
C11 C 0.6949(3) 0.9572(3) 0.42755(16) 0.0321(11) Uani 1 d . . .
C12 C 0.7648(3) 0.9213(3) 0.39948(17) 0.0339(11) Uani 1 d . . .
C13 C 0.7101(5) 1.2103(3) 0.4317(2) 0.0652(18) Uani 1 d . . .
H13A H 0.6424 1.2198 0.4134 0.098 Uiso 1 calc . . GR
H13B H 0.7613 1.2455 0.4182 0.098 Uiso 1 calc . . GR
H13C H 0.7086 1.2282 0.4646 0.098 Uiso 1 calc . . GR
C14 C 0.9070(4) 1.1143(3) 0.3457(2) 0.0443(13) Uani 1 d . . .
C15 C 0.8583(4) 1.1139(3) 0.2918(2) 0.0442(13) Uani 1 d . . .
C16 C 0.8951(5) 1.1180(4) 0.2120(2) 0.0684(18) Uani 1 d . . .
H16A H 0.8481 1.1685 0.2047 0.082 Uiso 1 calc . . R
H16B H 0.8573 1.0633 0.2021 0.082 Uiso 1 calc . . R
C17 C 0.9855(6) 1.1272(5) 0.1862(2) 0.078(2) Uani 1 d . . .
H17A H 0.9621 1.1306 0.1521 0.116 Uiso 1 calc . . GR
H17B H 1.0306 1.0760 0.1928 0.116 Uiso 1 calc . . GR
H17C H 1.0232 1.1809 0.1966 0.116 Uiso 1 calc . . GR
C18 C 0.8334(4) 0.7642(3) 0.38529(19) 0.0471(13) Uani 1 d . . .
H18A H 0.8040 0.7408 0.3544 0.071 Uiso 1 calc . . GR
H18B H 0.8463 0.7157 0.4080 0.071 Uiso 1 calc . . GR
H18C H 0.8981 0.7943 0.3824 0.071 Uiso 1 calc . . GR
C19 C 0.6875(3) 0.8047(3) 0.43143(17) 0.0337(11) Uani 1 d . . .
C20 C 0.6450(3) 0.8832(3) 0.44846(17) 0.0320(11) Uani 1 d . . .
C21 C 0.5723(4) 0.8783(3) 0.48002(18) 0.0386(12) Uani 1 d . . .
H21 H 0.5456 0.9302 0.4923 0.046 Uiso 1 calc . . R
C22 C 0.5402(4) 0.7948(3) 0.49296(18) 0.0388(12) Uani 1 d . . .
H22 H 0.4908 0.7905 0.5141 0.047 Uiso 1 calc . . R
C23 C 0.5803(4) 0.7162(3) 0.47512(18) 0.0365(12) Uani 1 d . . .
C24 C 0.6546(3) 0.7192(3) 0.44420(18) 0.0371(12) Uani 1 d . . .
H24 H 0.6817 0.6670 0.4324 0.045 Uiso 1 calc . . R
C25 C 0.5369(4) 0.6289(3) 0.4887(2) 0.0472(14) Uani 1 d . . .
C26 C 0.4252(4) 0.6142(3) 0.4659(2) 0.0437(13) Uani 1 d . . .
C27 C 0.3178(4) 0.5441(4) 0.4004(2) 0.0566(16) Uani 1 d . . .
H27A H 0.2811 0.5979 0.3880 0.068 Uiso 1 calc . . R
H27B H 0.2774 0.5151 0.4228 0.068 Uiso 1 calc . . R
C28 C 0.3328(5) 0.4819(4) 0.3602(2) 0.080(2) Uani 1 d . . .
H28A H 0.3677 0.5132 0.3369 0.121 Uiso 1 calc . . GR
H28B H 0.2658 0.4611 0.3449 0.121 Uiso 1 calc . . GR
H28C H 0.3745 0.4316 0.3727 0.121 Uiso 1 calc . . GR
Cl2 Cl 0.42732(15) 0.15070(13) 0.18582(6) 0.0843(6) Uani 1 d . . .
F5 F 0.3672(3) -0.2453(2) 0.36766(12) 0.0718(10) Uani 1 d . . .
F6 F 0.4907(2) -0.1549(2) 0.35371(11) 0.0578(9) Uani 1 d . . .
F7 F 0.1790(2) 0.4398(2) 0.48642(13) 0.0663(10) Uani 1 d . . .
F8 F 0.0365(3) 0.3970(2) 0.51444(12) 0.0642(9) Uani 1 d . . .
O6 O 0.2374(3) -0.1613(3) 0.29036(15) 0.0617(11) Uani 1 d . . .
O7 O 0.3982(3) -0.1605(2) 0.26849(13) 0.0517(10) Uani 1 d . . .
O8 O 0.0519(3) -0.0601(2) 0.43844(13) 0.0480(9) Uani 1 d . . .
O9 O 0.0651(3) 0.4753(3) 0.40324(17) 0.0776(13) Uani 1 d . . .
O10 O -0.0711(3) 0.3995(3) 0.42712(17) 0.0753(14) Uani 1 d . . .
N3 N 0.2876(3) 0.1472(3) 0.40333(15) 0.0373(10) Uani 1 d . . .
N4 N 0.2045(3) -0.1309(3) 0.43227(15) 0.0398(10) Uani 1 d . . .
C29 C 0.4568(4) 0.0369(3) 0.3162(2) 0.0452(13) Uani 1 d . . .
H29 H 0.5107 0.0154 0.3388 0.054 Uiso 1 calc . . R
C30 C 0.4795(4) 0.0738(4) 0.2730(2) 0.0482(14) Uani 1 d . . .
H30 H 0.5483 0.0771 0.2667 0.058 Uiso 1 calc . . R
C31 C 0.3997(5) 0.1050(3) 0.2402(2) 0.0512(14) Uani 1 d . . .
C32 C 0.2974(5) 0.1023(4) 0.2490(2) 0.0544(15) Uani 1 d . . .
H32 H 0.2442 0.1253 0.2265 0.065 Uiso 1 calc . . R
C33 C 0.2742(4) 0.0650(3) 0.29183(19) 0.0447(13) Uani 1 d . . .
H33 H 0.2052 0.0622 0.2979 0.054 Uiso 1 calc . . R
C34 C 0.3543(4) 0.0321(3) 0.32546(18) 0.0387(12) Uani 1 d . . .
C35 C 0.3282(3) -0.0048(3) 0.37238(17) 0.0377(12) Uani 1 d . . .
C36 C 0.2761(3) 0.0532(3) 0.40347(17) 0.0358(11) Uani 1 d . . .
C37 C 0.1989(3) 0.0315(3) 0.43151(17) 0.0358(11) Uani 1 d . . .
C38 C 0.1456(4) -0.0567(3) 0.43464(18) 0.0417(12) Uani 1 d . . .
C39 C 0.3168(4) -0.1242(3) 0.43272(18) 0.0396(12) Uani 1 d . . .
H39A H 0.3483 -0.1826 0.4402 0.047 Uiso 1 calc . . R
H39B H 0.3453 -0.0827 0.4580 0.047 Uiso 1 calc . . R
C40 C 0.3452(4) -0.0924(3) 0.38547(18) 0.0386(12) Uani 1 d . . .
C41 C 0.3840(4) -0.1601(3) 0.35198(19) 0.0431(13) Uani 1 d . . .
C42 C 0.3303(4) -0.1594(3) 0.2995(2) 0.0435(13) Uani 1 d . . .
C43 C 0.3549(5) -0.1626(4) 0.2176(2) 0.0648(17) Uani 1 d . . .
H43A H 0.3109 -0.1104 0.2094 0.078 Uiso 1 calc . . R
H43B H 0.3129 -0.2162 0.2104 0.078 Uiso 1 calc . . R
C44 C 0.4456(6) -0.1623(6) 0.1895(3) 0.095(2) Uani 1 d . . .
H44A H 0.4202 -0.1620 0.1556 0.142 Uiso 1 calc . . GR
H44B H 0.4874 -0.2151 0.1974 0.142 Uiso 1 calc . . GR
H44C H 0.4875 -0.1098 0.1977 0.142 Uiso 1 calc . . GR
C45 C 0.1542(4) -0.2180(3) 0.4249(2) 0.0580(16) Uani 1 d . . .
H45A H 0.1784 -0.2476 0.3980 0.087 Uiso 1 calc . . GR
H45B H 0.0797 -0.2100 0.4183 0.087 Uiso 1 calc . . GR
H45C H 0.1711 -0.2539 0.4534 0.087 Uiso 1 calc . . GR
C46 C 0.2180(3) 0.1832(3) 0.43146(17) 0.0362(11) Uani 1 d . . .
C47 C 0.1617(3) 0.1131(3) 0.44978(17) 0.0345(11) Uani 1 d . . .
C48 C 0.0873(4) 0.1330(4) 0.47976(19) 0.0436(13) Uani 1 d . . .
H48 H 0.0517 0.0876 0.4935 0.052 Uiso 1 calc . . R
C49 C 0.0676(4) 0.2234(3) 0.48860(19) 0.0432(13) Uani 1 d . . .
H49 H 0.0175 0.2381 0.5082 0.052 Uiso 1 calc . . R
C50 C 0.1205(4) 0.2913(3) 0.46896(18) 0.0402(12) Uani 1 d . . .
C51 C 0.1992(4) 0.2736(3) 0.44058(18) 0.0393(12) Uani 1 d . . .
H51 H 0.2370 0.3195 0.4284 0.047 Uiso 1 calc . . R
C52 C 0.0913(4) 0.3870(4) 0.4758(2) 0.0482(14) Uani 1 d . . .
C53 C 0.0265(5) 0.4265(4) 0.4311(2) 0.0549(15) Uani 1 d . . .
C54 C -0.1406(5) 0.4285(6) 0.3834(3) 0.101(3) Uani 1 d . . .
H54A H -0.1005 0.4626 0.3627 0.122 Uiso 1 calc . . R
H54B H -0.1692 0.3761 0.3656 0.122 Uiso 1 calc . . R
C55 C -0.2217(9) 0.4813(7) 0.3956(4) 0.203(7) Uani 1 d . . .
H55A H -0.2580 0.5089 0.3671 0.304 Uiso 1 calc . . GR
H55B H -0.1937 0.5271 0.4180 0.304 Uiso 1 calc . . GR
H55C H -0.2695 0.4443 0.4103 0.304 Uiso 1 calc . . GR
C59 C 0.3689(4) 0.1990(3) 0.38495(18) 0.0408(12) Uani 1 d . . .
H59A H 0.3481 0.2117 0.3513 0.061 Uiso 1 calc . . GR
H59B H 0.4330 0.1652 0.3889 0.061 Uiso 1 calc . . GR
H59C H 0.3795 0.2545 0.4025 0.061 Uiso 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
Cl1 C3 1.733(5) . ?
F1 C14 1.356(5) . ?
F2 C14 1.386(6) . ?
F3 C25 1.361(6) . ?
F4 C25 1.385(6) . ?
O1 C15 1.184(5) . ?
O2 C15 1.318(6) . ?
O2 C16 1.454(7) . ?
O3 C10 1.240(5) . ?
O4 C26 1.344(6) . ?
O4 C27 1.472(6) . ?
O5 C26 1.193(6) . ?
N1 C12 1.403(6) . ?
N1 C18 1.447(6) . ?
N1 C19 1.379(6) . ?
N2 C9 1.454(6) . ?
N2 C10 1.346(6) . ?
N2 C13 1.462(6) . ?
C0AA H0AA 0.9300 . ?
C0AA C2 1.363(7) . ?
C0AA C6 1.391(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(7) . ?
C3 C4 1.373(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(7) . ?
C6 C7 1.484(7) . ?
C7 C8 1.369(6) . ?
C7 C12 1.468(6) . ?
C8 C9 1.503(7) . ?
C8 C14 1.488(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.474(6) . ?
C11 C12 1.383(6) . ?
C11 C20 1.440(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.549(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.461(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.402(6) . ?
C19 C24 1.403(6) . ?
C20 C21 1.376(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.398(6) . ?
C23 C24 1.378(7) . ?
C23 C25 1.486(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.508(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.490(8) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
Cl2 C31 1.748(6) . ?
F5 C41 1.369(6) . ?
F6 C41 1.373(5) . ?
F7 C52 1.375(6) . ?
F8 C52 1.379(6) . ?
O6 C42 1.191(6) . ?
O7 C42 1.317(6) . ?
O7 C43 1.455(6) . ?
O8 C38 1.229(5) . ?
O9 C53 1.221(7) . ?
O10 C53 1.312(7) . ?
O10 C54 1.477(7) . ?
N3 C36 1.407(6) . ?
N3 C46 1.381(6) . ?
N3 C59 1.452(6) . ?
N4 C38 1.347(6) . ?
N4 C39 1.450(6) . ?
N4 C45 1.450(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.393(7) . ?
C29 C34 1.384(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.362(7) . ?
C31 C32 1.376(7) . ?
C32 H32 0.9300 . ?
C32 C33 1.389(7) . ?
C33 H33 0.9300 . ?
C33 C34 1.386(7) . ?
C34 C35 1.503(7) . ?
C35 C36 1.454(6) . ?
C35 C40 1.363(6) . ?
C36 C37 1.389(6) . ?
C37 C38 1.488(7) . ?
C37 C47 1.426(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.496(7) . ?
C40 C41 1.507(7) . ?
C41 C42 1.532(7) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 C44 1.497(8) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 C47 1.407(7) . ?
C46 C51 1.397(7) . ?
C47 C48 1.391(7) . ?
C48 H48 0.9300 . ?
C48 C49 1.397(7) . ?
C49 H49 0.9300 . ?
C49 C50 1.375(7) . ?
C50 C51 1.398(7) . ?
C50 C52 1.492(7) . ?
C51 H51 0.9300 . ?
C52 C53 1.521(8) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C54 C55 1.389(11) . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 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
C15 O2 C16 115.5(4) . . ?
C26 O4 C27 115.0(4) . . ?
C12 N1 C18 126.9(4) . . ?
C19 N1 C12 107.8(4) . . ?
C19 N1 C18 124.3(4) . . ?
C9 N2 C13 119.5(4) . . ?
C10 N2 C9 120.4(4) . . ?
C10 N2 C13 120.1(4) . . ?
C2 C0AA H0AA 119.3 . . ?
C2 C0AA C6 121.5(5) . . ?
C6 C0AA H0AA 119.3 . . ?
C0AA C2 H2 120.4 . . ?
C0AA C2 C3 119.2(5) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 Cl1 119.1(4) . . ?
C4 C3 Cl1 119.2(4) . . ?
C4 C3 C2 121.7(5) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.5(5) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.6 . . ?
C0AA C6 C7 120.8(5) . . ?
C5 C6 C0AA 118.3(5) . . ?
C5 C6 C7 120.8(4) . . ?
C8 C7 C6 123.0(4) . . ?
C8 C7 C12 117.6(4) . . ?
C12 C7 C6 119.3(4) . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 C14 123.2(5) . . ?
C14 C8 C9 117.7(4) . . ?
N2 C9 C8 111.5(4) . . ?
N2 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
O3 C10 N2 122.0(4) . . ?
O3 C10 C11 120.4(4) . . ?
N2 C10 C11 117.6(4) . . ?
C12 C11 C10 128.9(4) . . ?
C12 C11 C20 107.4(4) . . ?
C20 C11 C10 123.4(4) . . ?
N1 C12 C7 122.5(4) . . ?
C11 C12 N1 109.0(4) . . ?
C11 C12 C7 128.0(4) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F1 C14 F2 104.7(4) . . ?
F1 C14 C8 112.0(4) . . ?
F1 C14 C15 110.7(4) . . ?
F2 C14 C8 108.5(4) . . ?
F2 C14 C15 102.5(4) . . ?
C8 C14 C15 117.1(4) . . ?
O1 C15 O2 127.8(5) . . ?
O1 C15 C14 121.3(5) . . ?
O2 C15 C14 110.7(4) . . ?
O2 C16 H16A 110.0 . . ?
O2 C16 H16B 110.0 . . ?
O2 C16 C17 108.6(5) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 109.5(4) . . ?
N1 C19 C24 129.0(4) . . ?
C20 C19 C24 121.5(4) . . ?
C19 C20 C11 106.3(4) . . ?
C21 C20 C11 133.2(4) . . ?
C21 C20 C19 120.5(4) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 C20 118.3(5) . . ?
C22 C21 H21 120.8 . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.5(5) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C25 118.0(5) . . ?
C24 C23 C22 121.4(4) . . ?
C24 C23 C25 120.6(5) . . ?
C19 C24 H24 121.6 . . ?
C23 C24 C19 116.7(4) . . ?
C23 C24 H24 121.6 . . ?
F3 C25 F4 105.2(4) . . ?
F3 C25 C23 112.1(4) . . ?
F3 C25 C26 111.0(4) . . ?
F4 C25 C23 109.8(4) . . ?
F4 C25 C26 105.2(4) . . ?
C23 C25 C26 113.0(4) . . ?
O4 C26 C25 109.9(5) . . ?
O5 C26 O4 124.9(5) . . ?
O5 C26 C25 125.0(5) . . ?
O4 C27 H27A 110.4 . . ?
O4 C27 H27B 110.4 . . ?
O4 C27 C28 106.5(5) . . ?
H27A C27 H27B 108.6 . . ?
C28 C27 H27A 110.4 . . ?
C28 C27 H27B 110.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C42 O7 C43 116.4(5) . . ?
C53 O10 C54 116.5(5) . . ?
C36 N3 C59 127.6(4) . . ?
C46 N3 C36 107.8(4) . . ?
C46 N3 C59 123.7(4) . . ?
C38 N4 C39 120.8(4) . . ?
C38 N4 C45 119.7(4) . . ?
C39 N4 C45 119.3(4) . . ?
C30 C29 H29 119.9 . . ?
C34 C29 H29 119.9 . . ?
C34 C29 C30 120.3(5) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 C29 119.2(5) . . ?
C31 C30 H30 120.4 . . ?
C30 C31 Cl2 119.5(5) . . ?
C30 C31 C32 121.6(5) . . ?
C32 C31 Cl2 118.9(4) . . ?
C31 C32 H32 120.3 . . ?
C31 C32 C33 119.5(5) . . ?
C33 C32 H32 120.3 . . ?
C32 C33 H33 120.1 . . ?
C34 C33 C32 119.8(5) . . ?
C34 C33 H33 120.1 . . ?
C29 C34 C33 119.7(5) . . ?
C29 C34 C35 121.2(4) . . ?
C33 C34 C35 119.1(4) . . ?
C36 C35 C34 118.9(4) . . ?
C40 C35 C34 122.5(4) . . ?
C40 C35 C36 118.5(5) . . ?
N3 C36 C35 122.1(4) . . ?
C37 C36 N3 108.5(4) . . ?
C37 C36 C35 128.8(4) . . ?
C36 C37 C38 127.7(4) . . ?
C36 C37 C47 107.9(4) . . ?
C47 C37 C38 123.3(4) . . ?
O8 C38 N4 122.5(5) . . ?
O8 C38 C37 120.6(4) . . ?
N4 C38 C37 116.9(4) . . ?
N4 C39 H39A 109.1 . . ?
N4 C39 H39B 109.1 . . ?
N4 C39 C40 112.4(4) . . ?
H39A C39 H39B 107.9 . . ?
C40 C39 H39A 109.1 . . ?
C40 C39 H39B 109.1 . . ?
C35 C40 C39 119.3(4) . . ?
C35 C40 C41 121.8(5) . . ?
C39 C40 C41 118.8(4) . . ?
F5 C41 F6 104.2(4) . . ?
F5 C41 C40 109.8(4) . . ?
F5 C41 C42 104.0(4) . . ?
F6 C41 C40 111.0(4) . . ?
F6 C41 C42 110.6(4) . . ?
C40 C41 C42 116.4(4) . . ?
O6 C42 O7 126.9(5) . . ?
O6 C42 C41 120.9(5) . . ?
O7 C42 C41 112.1(5) . . ?
O7 C43 H43A 110.4 . . ?
O7 C43 H43B 110.4 . . ?
O7 C43 C44 106.9(5) . . ?
H43A C43 H43B 108.6 . . ?
C44 C43 H43A 110.4 . . ?
C44 C43 H43B 110.4 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N4 C45 H45A 109.5 . . ?
N4 C45 H45B 109.5 . . ?
N4 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N3 C46 C47 109.3(4) . . ?
N3 C46 C51 128.3(5) . . ?
C51 C46 C47 122.4(5) . . ?
C46 C47 C37 106.5(4) . . ?
C48 C47 C37 133.8(5) . . ?
C48 C47 C46 119.7(5) . . ?
C47 C48 H48 121.0 . . ?
C47 C48 C49 118.0(5) . . ?
C49 C48 H48 121.0 . . ?
C48 C49 H49 119.2 . . ?
C50 C49 C48 121.6(5) . . ?
C50 C49 H49 119.2 . . ?
C49 C50 C51 121.9(5) . . ?
C49 C50 C52 120.1(5) . . ?
C51 C50 C52 118.0(5) . . ?
C46 C51 C50 116.3(5) . . ?
C46 C51 H51 121.8 . . ?
C50 C51 H51 121.8 . . ?
F7 C52 F8 105.4(4) . . ?
F7 C52 C50 110.9(4) . . ?
F7 C52 C53 107.4(5) . . ?
F8 C52 C50 111.6(5) . . ?
F8 C52 C53 108.7(4) . . ?
C50 C52 C53 112.5(4) . . ?
O9 C53 O10 126.8(6) . . ?
O9 C53 C52 121.9(6) . . ?
O10 C53 C52 111.3(5) . . ?
O10 C54 H54A 109.5 . . ?
O10 C54 H54B 109.5 . . ?
H54A C54 H54B 108.1 . . ?
C55 C54 O10 110.6(7) . . ?
C55 C54 H54A 109.5 . . ?
C55 C54 H54B 109.5 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
N3 C59 H59A 109.5 . . ?
N3 C59 H59B 109.5 . . ?
N3 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 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
Cl1 C3 C4 C5 179.3(4) . . . . ?
F1 C14 C15 O1 176.1(4) . . . . ?
F1 C14 C15 O2 -7.9(5) . . . . ?
F2 C14 C15 O1 -72.6(6) . . . . ?
F2 C14 C15 O2 103.4(4) . . . . ?
F3 C25 C26 O4 -32.4(6) . . . . ?
F3 C25 C26 O5 151.5(5) . . . . ?
F4 C25 C26 O4 -145.7(4) . . . . ?
F4 C25 C26 O5 38.1(6) . . . . ?
O3 C10 C11 C12 144.3(5) . . . . ?
O3 C10 C11 C20 -28.1(7) . . . . ?
N1 C19 C20 C11 0.7(5) . . . . ?
N1 C19 C20 C21 -177.7(4) . . . . ?
N1 C19 C24 C23 179.1(5) . . . . ?
N2 C10 C11 C12 -35.0(7) . . . . ?
N2 C10 C11 C20 152.7(4) . . . . ?
C0AA C2 C3 Cl1 -179.7(4) . . . . ?
C0AA C2 C3 C4 0.7(8) . . . . ?
C0AA C6 C7 C8 -126.0(5) . . . . ?
C0AA C6 C7 C12 49.6(6) . . . . ?
C2 C0AA C6 C5 -1.8(7) . . . . ?
C2 C0AA C6 C7 -178.0(5) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C4 C5 C6 C0AA 1.4(7) . . . . ?
C4 C5 C6 C7 177.7(4) . . . . ?
C5 C6 C7 C8 57.9(7) . . . . ?
C5 C6 C7 C12 -126.5(5) . . . . ?
C6 C0AA C2 C3 0.7(8) . . . . ?
C6 C7 C8 C9 -176.3(4) . . . . ?
C6 C7 C8 C14 4.8(8) . . . . ?
C6 C7 C12 N1 29.7(7) . . . . ?
C6 C7 C12 C11 -141.6(5) . . . . ?
C7 C8 C9 N2 -75.9(6) . . . . ?
C7 C8 C14 F1 -89.6(6) . . . . ?
C7 C8 C14 F2 155.2(5) . . . . ?
C7 C8 C14 C15 39.9(7) . . . . ?
C8 C7 C12 N1 -154.5(4) . . . . ?
C8 C7 C12 C11 34.3(7) . . . . ?
C8 C14 C15 O1 46.0(7) . . . . ?
C8 C14 C15 O2 -138.0(5) . . . . ?
C9 N2 C10 O3 175.0(4) . . . . ?
C9 N2 C10 C11 -5.7(6) . . . . ?
C9 C8 C14 F1 91.6(5) . . . . ?
C9 C8 C14 F2 -23.6(6) . . . . ?
C9 C8 C14 C15 -138.9(5) . . . . ?
C10 N2 C9 C8 74.0(5) . . . . ?
C10 C11 C12 N1 -173.4(4) . . . . ?
C10 C11 C12 C7 -1.2(8) . . . . ?
C10 C11 C20 C19 173.4(4) . . . . ?
C10 C11 C20 C21 -8.5(8) . . . . ?
C11 C20 C21 C22 179.9(5) . . . . ?
C12 N1 C19 C20 -0.8(5) . . . . ?
C12 N1 C19 C24 178.8(4) . . . . ?
C12 C7 C8 C9 8.0(7) . . . . ?
C12 C7 C8 C14 -170.8(4) . . . . ?
C12 C11 C20 C19 -0.4(5) . . . . ?
C12 C11 C20 C21 177.7(5) . . . . ?
C13 N2 C9 C8 -107.8(5) . . . . ?
C13 N2 C10 O3 -3.1(7) . . . . ?
C13 N2 C10 C11 176.1(5) . . . . ?
C14 C8 C9 N2 103.0(5) . . . . ?
C15 O2 C16 C17 175.0(5) . . . . ?
C16 O2 C15 O1 -2.3(8) . . . . ?
C16 O2 C15 C14 -178.0(4) . . . . ?
C18 N1 C12 C7 19.1(7) . . . . ?
C18 N1 C12 C11 -168.2(4) . . . . ?
C18 N1 C19 C20 168.3(4) . . . . ?
C18 N1 C19 C24 -12.2(8) . . . . ?
C19 N1 C12 C7 -172.2(4) . . . . ?
C19 N1 C12 C11 0.5(5) . . . . ?
C19 C20 C21 C22 -2.2(7) . . . . ?
C20 C11 C12 N1 -0.1(5) . . . . ?
C20 C11 C12 C7 172.1(4) . . . . ?
C20 C19 C24 C23 -1.4(7) . . . . ?
C20 C21 C22 C23 0.5(7) . . . . ?
C21 C22 C23 C24 0.8(7) . . . . ?
C21 C22 C23 C25 -176.5(4) . . . . ?
C22 C23 C24 C19 -0.3(7) . . . . ?
C22 C23 C25 F3 -164.5(4) . . . . ?
C22 C23 C25 F4 -47.9(6) . . . . ?
C22 C23 C25 C26 69.1(6) . . . . ?
C23 C25 C26 O4 94.6(5) . . . . ?
C23 C25 C26 O5 -81.6(7) . . . . ?
C24 C19 C20 C11 -178.9(4) . . . . ?
C24 C19 C20 C21 2.7(7) . . . . ?
C24 C23 C25 F3 18.2(7) . . . . ?
C24 C23 C25 F4 134.8(5) . . . . ?
C24 C23 C25 C26 -108.2(6) . . . . ?
C25 C23 C24 C19 176.9(4) . . . . ?
C26 O4 C27 C28 -172.4(5) . . . . ?
C27 O4 C26 O5 -6.9(7) . . . . ?
C27 O4 C26 C25 176.9(4) . . . . ?
Cl2 C31 C32 C33 179.1(4) . . . . ?
F5 C41 C42 O6 70.6(6) . . . . ?
F5 C41 C42 O7 -106.7(5) . . . . ?
F6 C41 C42 O6 -178.1(4) . . . . ?
F6 C41 C42 O7 4.5(5) . . . . ?
F7 C52 C53 O9 21.2(7) . . . . ?
F7 C52 C53 O10 -160.1(4) . . . . ?
F8 C52 C53 O9 134.8(6) . . . . ?
F8 C52 C53 O10 -46.6(6) . . . . ?
N3 C36 C37 C38 167.2(4) . . . . ?
N3 C36 C37 C47 -0.6(5) . . . . ?
N3 C46 C47 C37 -0.4(5) . . . . ?
N3 C46 C47 C48 179.3(4) . . . . ?
N3 C46 C51 C50 177.3(4) . . . . ?
N4 C39 C40 C35 72.3(6) . . . . ?
N4 C39 C40 C41 -103.0(5) . . . . ?
C29 C30 C31 Cl2 -179.6(4) . . . . ?
C29 C30 C31 C32 1.1(8) . . . . ?
C29 C34 C35 C36 119.1(5) . . . . ?
C29 C34 C35 C40 -65.4(7) . . . . ?
C30 C29 C34 C33 -0.7(7) . . . . ?
C30 C29 C34 C35 -178.1(4) . . . . ?
C30 C31 C32 C33 -1.6(8) . . . . ?
C31 C32 C33 C34 0.9(8) . . . . ?
C32 C33 C34 C29 0.2(7) . . . . ?
C32 C33 C34 C35 177.7(5) . . . . ?
C33 C34 C35 C36 -58.4(6) . . . . ?
C33 C34 C35 C40 117.1(5) . . . . ?
C34 C29 C30 C31 0.0(8) . . . . ?
C34 C35 C36 N3 -27.5(7) . . . . ?
C34 C35 C36 C37 142.3(5) . . . . ?
C34 C35 C40 C39 -179.7(4) . . . . ?
C34 C35 C40 C41 -4.6(7) . . . . ?
C35 C36 C37 C38 -3.6(8) . . . . ?
C35 C36 C37 C47 -171.4(4) . . . . ?
C35 C40 C41 F5 -163.4(4) . . . . ?
C35 C40 C41 F6 82.0(6) . . . . ?
C35 C40 C41 C42 -45.7(7) . . . . ?
C36 N3 C46 C47 0.0(5) . . . . ?
C36 N3 C46 C51 -177.8(4) . . . . ?
C36 C35 C40 C39 -4.3(7) . . . . ?
C36 C35 C40 C41 170.9(4) . . . . ?
C36 C37 C38 O8 -142.3(5) . . . . ?
C36 C37 C38 N4 36.7(7) . . . . ?
C36 C37 C47 C46 0.6(5) . . . . ?
C36 C37 C47 C48 -179.0(5) . . . . ?
C37 C47 C48 C49 -177.3(5) . . . . ?
C38 N4 C39 C40 -75.3(6) . . . . ?
C38 C37 C47 C46 -167.9(4) . . . . ?
C38 C37 C47 C48 12.5(8) . . . . ?
C39 N4 C38 O8 -173.7(4) . . . . ?
C39 N4 C38 C37 7.4(7) . . . . ?
C39 C40 C41 F5 11.8(6) . . . . ?
C39 C40 C41 F6 -102.8(5) . . . . ?
C39 C40 C41 C42 129.5(5) . . . . ?
C40 C35 C36 N3 156.9(4) . . . . ?
C40 C35 C36 C37 -33.3(7) . . . . ?
C40 C41 C42 O6 -50.3(6) . . . . ?
C40 C41 C42 O7 132.4(5) . . . . ?
C42 O7 C43 C44 179.3(5) . . . . ?
C43 O7 C42 O6 1.2(7) . . . . ?
C43 O7 C42 C41 178.3(4) . . . . ?
C45 N4 C38 O8 11.8(8) . . . . ?
C45 N4 C38 C37 -167.1(5) . . . . ?
C45 N4 C39 C40 99.2(5) . . . . ?
C46 N3 C36 C35 172.0(4) . . . . ?
C46 N3 C36 C37 0.3(5) . . . . ?
C46 C47 C48 C49 3.2(7) . . . . ?
C47 C37 C38 O8 23.8(7) . . . . ?
C47 C37 C38 N4 -157.2(5) . . . . ?
C47 C46 C51 C50 -0.2(7) . . . . ?
C47 C48 C49 C50 -0.8(7) . . . . ?
C48 C49 C50 C51 -2.3(7) . . . . ?
C48 C49 C50 C52 174.9(4) . . . . ?
C49 C50 C51 C46 2.7(7) . . . . ?
C49 C50 C52 F7 137.2(5) . . . . ?
C49 C50 C52 F8 20.0(7) . . . . ?
C49 C50 C52 C53 -102.5(6) . . . . ?
C50 C52 C53 O9 -101.1(6) . . . . ?
C50 C52 C53 O10 77.6(6) . . . . ?
C51 C46 C47 C37 177.6(4) . . . . ?
C51 C46 C47 C48 -2.7(7) . . . . ?
C51 C50 C52 F7 -45.5(6) . . . . ?
C51 C50 C52 F8 -162.7(4) . . . . ?
C51 C50 C52 C53 74.8(6) . . . . ?
C52 C50 C51 C46 -174.5(4) . . . . ?
C53 O10 C54 C55 -118.2(9) . . . . ?
C54 O10 C53 O9 2.4(9) . . . . ?
C54 O10 C53 C52 -176.1(6) . . . . ?
C59 N3 C36 C35 -18.3(7) . . . . ?
C59 N3 C36 C37 170.1(4) . . . . ?
C59 N3 C46 C47 -170.2(4) . . . . ?
C59 N3 C46 C51 12.0(8) . . . . ?

_olex2_date_sample_data_collection 2016-06-15
_olex2_submission_special_instructions 'No special instructions were received'
