# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_sa
_database_code_depnum_ccdc_archive 'CCDC 1427844'
_audit_update_record             
;
2015-11-11 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 F4 N O2'
_chemical_formula_weight         351.29

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                   12.352(3)
_cell_length_b                   9.5750(19)
_cell_length_c                   13.866(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.33(3)
_cell_angle_gamma                90
_cell_volume                     1573.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5299
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   CrystalClear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
; 
Rigaku Saturn 724 CCD 
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 14.2
_diffrn_reflns_number            18292
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         27.950
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3755
_reflns_number_gt                2913
_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       
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_cell_refinement       
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_data_reduction        
; 
Rigaku CrystalClear-SM Expert 2.0 r4 
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0539P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3755
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.44397(6) 0.43005(8) 0.40349(5) 0.0321(2) Uani 1 1 d . . . . .
F2 F 0.37443(6) 0.35840(8) 0.52088(5) 0.02750(18) Uani 1 1 d . . . . .
F3 F 0.29499(6) 0.52866(7) 0.42415(5) 0.02938(19) Uani 1 1 d . . . . .
F4 F -0.34413(6) 0.30730(8) 0.38439(6) 0.03053(19) Uani 1 1 d . . . . .
O1 O 0.26546(7) 0.36803(8) 0.25676(6) 0.02040(19) Uani 1 1 d . . . . .
O2 O 0.15070(7) 0.28213(10) 0.45700(6) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.06332(8) 0.30751(10) 0.29042(7) 0.0184(2) Uani 1 1 d . . . . .
C1 C 0.34769(10) 0.40514(13) 0.42631(9) 0.0220(3) Uani 1 1 d . . . . .
C2 C 0.27335(9) 0.30213(12) 0.35047(8) 0.0178(2) Uani 1 1 d . . . . .
C3 C 0.15726(10) 0.29552(12) 0.37121(8) 0.0182(2) Uani 1 1 d . . . . .
C4 C 0.06689(10) 0.31787(12) 0.18866(9) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.18276(10) 0.30026(13) 0.17652(8) 0.0225(3) Uani 1 1 d . . . . .
H5A H 0.2007 0.1995 0.1761 0.027 Uiso 1 1 calc R U . . .
H5B H 0.1852 0.3406 0.1114 0.027 Uiso 1 1 calc R U . . .
C6 C -0.02418(11) 0.33787(15) 0.11159(10) 0.0310(3) Uani 1 1 d . . . . .
H6A H -0.0963 0.3460 0.1229 0.037 Uiso 1 1 calc R U . . .
H6B H -0.0171 0.3440 0.0452 0.037 Uiso 1 1 calc R U . . .
C7 C 0.33006(9) 0.15796(12) 0.35849(9) 0.0195(2) Uani 1 1 d . . . . .
C8 C 0.41199(10) 0.13621(14) 0.30836(10) 0.0268(3) Uani 1 1 d . . . . .
H8 H 0.4315 0.2099 0.2705 0.032 Uiso 1 1 calc R U . . .
C9 C 0.46506(10) 0.00765(15) 0.31344(10) 0.0326(3) Uani 1 1 d . . . . .
H9 H 0.5205 -0.0065 0.2788 0.039 Uiso 1 1 calc R U . . .
C10 C 0.43753(11) -0.10019(14) 0.36891(10) 0.0332(3) Uani 1 1 d . . . . .
H10 H 0.4739 -0.1882 0.3722 0.040 Uiso 1 1 calc R U . . .
C11 C 0.35746(11) -0.07950(14) 0.41923(10) 0.0316(3) Uani 1 1 d . . . . .
H11 H 0.3390 -0.1534 0.4575 0.038 Uiso 1 1 calc R U . . .
C12 C 0.30328(10) 0.04910(13) 0.41449(9) 0.0251(3) Uani 1 1 d . . . . .
H12 H 0.2481 0.0626 0.4494 0.030 Uiso 1 1 calc R U . . .
C13 C -0.04474(9) 0.30864(12) 0.31335(8) 0.0186(2) Uani 1 1 d . . . . .
C14 C -0.11593(10) 0.19445(12) 0.28783(9) 0.0235(3) Uani 1 1 d . . . . .
H14 H -0.0949 0.1167 0.2545 0.028 Uiso 1 1 calc R U . . .
C15 C -0.21817(10) 0.19419(13) 0.31122(10) 0.0256(3) Uani 1 1 d . . . . .
H15 H -0.2687 0.1175 0.2933 0.031 Uiso 1 1 calc R U . . .
C16 C -0.24424(10) 0.30777(13) 0.36090(9) 0.0216(3) Uani 1 1 d . . . . .
C17 C -0.17453(10) 0.42183(12) 0.38844(9) 0.0220(3) Uani 1 1 d . . . . .
H17 H -0.1951 0.4979 0.4236 0.026 Uiso 1 1 calc R U . . .
C18 C -0.07294(10) 0.42252(12) 0.36320(9) 0.0206(2) Uani 1 1 d . . . . .
H18 H -0.0235 0.5003 0.3800 0.025 Uiso 1 1 calc R U . . .


_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 C1 1.3353(13) . ?
F2 C1 1.3362(14) . ?
F3 C1 1.3463(14) . ?
F4 C16 1.3617(13) . ?
O1 C2 1.4229(13) . ?
O1 C5 1.4364(15) . ?
O2 C3 1.2216(14) . ?
N1 C3 1.3724(15) . ?
N1 C4 1.4275(15) . ?
N1 C13 1.4565(14) . ?
C1 C2 1.5423(16) . ?
C2 C7 1.5378(16) . ?
C2 C3 1.5410(15) . ?
C4 C6 1.3297(18) . ?
C4 C5 1.4969(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9500 . ?
C6 H6B 0.9500 . ?
C7 C12 1.3939(17) . ?
C7 C8 1.3951(17) . ?
C8 C9 1.3871(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3756(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3942(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3853(16) . ?
C13 C18 1.3869(16) . ?
C14 C15 1.3894(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3732(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3766(16) . ?
C17 C18 1.3943(16) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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 O1 C5 110.99(9) . . ?
C3 N1 C4 123.96(10) . . ?
C3 N1 C13 116.03(9) . . ?
C4 N1 C13 120.01(10) . . ?
F1 C1 F2 107.55(10) . . ?
F1 C1 F3 107.17(10) . . ?
F2 C1 F3 107.49(9) . . ?
F1 C1 C2 110.60(9) . . ?
F2 C1 C2 112.98(10) . . ?
F3 C1 C2 110.80(10) . . ?
O1 C2 C7 112.14(9) . . ?
O1 C2 C3 111.11(9) . . ?
C7 C2 C3 112.24(9) . . ?
O1 C2 C1 102.35(9) . . ?
C7 C2 C1 110.67(10) . . ?
C3 C2 C1 107.81(9) . . ?
O2 C3 N1 122.09(10) . . ?
O2 C3 C2 120.40(10) . . ?
N1 C3 C2 117.50(9) . . ?
C6 C4 N1 123.38(11) . . ?
C6 C4 C5 123.06(11) . . ?
N1 C4 C5 113.55(10) . . ?
O1 C5 C4 110.87(9) . . ?
O1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C4 C6 H6A 120.0 . . ?
C4 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
C12 C7 C8 119.01(11) . . ?
C12 C7 C2 122.48(10) . . ?
C8 C7 C2 118.51(10) . . ?
C9 C8 C7 120.38(12) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.21(12) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.86(12) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.49(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.05(12) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C18 121.16(10) . . ?
C14 C13 N1 119.56(10) . . ?
C18 C13 N1 119.25(10) . . ?
C13 C14 C15 119.68(11) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 118.19(11) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
F4 C16 C15 118.25(10) . . ?
F4 C16 C17 118.33(10) . . ?
C15 C16 C17 123.42(11) . . ?
C16 C17 C18 118.10(11) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C13 C18 C17 119.42(11) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?

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
C5 O1 C2 C7 71.51(11) . . . . ?
C5 O1 C2 C3 -55.01(12) . . . . ?
C5 O1 C2 C1 -169.86(9) . . . . ?
F1 C1 C2 O1 -54.27(12) . . . . ?
F2 C1 C2 O1 -174.89(9) . . . . ?
F3 C1 C2 O1 64.42(11) . . . . ?
F1 C1 C2 C7 65.40(12) . . . . ?
F2 C1 C2 C7 -55.22(12) . . . . ?
F3 C1 C2 C7 -175.91(9) . . . . ?
F1 C1 C2 C3 -171.51(9) . . . . ?
F2 C1 C2 C3 67.87(12) . . . . ?
F3 C1 C2 C3 -52.81(12) . . . . ?
C4 N1 C3 O2 -177.47(11) . . . . ?
C13 N1 C3 O2 2.23(16) . . . . ?
C4 N1 C3 C2 3.60(16) . . . . ?
C13 N1 C3 C2 -176.70(9) . . . . ?
O1 C2 C3 O2 -158.23(10) . . . . ?
C7 C2 C3 O2 75.30(13) . . . . ?
C1 C2 C3 O2 -46.83(14) . . . . ?
O1 C2 C3 N1 20.73(14) . . . . ?
C7 C2 C3 N1 -105.74(11) . . . . ?
C1 C2 C3 N1 132.12(10) . . . . ?
C3 N1 C4 C6 -175.81(12) . . . . ?
C13 N1 C4 C6 4.50(17) . . . . ?
C3 N1 C4 C5 5.72(15) . . . . ?
C13 N1 C4 C5 -173.96(10) . . . . ?
C2 O1 C5 C4 65.76(12) . . . . ?
C6 C4 C5 O1 142.32(12) . . . . ?
N1 C4 C5 O1 -39.21(13) . . . . ?
O1 C2 C7 C12 -149.28(11) . . . . ?
C3 C2 C7 C12 -23.37(15) . . . . ?
C1 C2 C7 C12 97.12(13) . . . . ?
O1 C2 C7 C8 31.26(14) . . . . ?
C3 C2 C7 C8 157.17(10) . . . . ?
C1 C2 C7 C8 -82.34(13) . . . . ?
C12 C7 C8 C9 0.65(18) . . . . ?
C2 C7 C8 C9 -179.87(11) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C8 C7 C12 C11 -0.47(18) . . . . ?
C2 C7 C12 C11 -179.93(11) . . . . ?
C10 C11 C12 C7 -0.01(19) . . . . ?
C3 N1 C13 C14 -109.14(12) . . . . ?
C4 N1 C13 C14 70.57(14) . . . . ?
C3 N1 C13 C18 68.90(14) . . . . ?
C4 N1 C13 C18 -111.39(12) . . . . ?
C18 C13 C14 C15 0.86(18) . . . . ?
N1 C13 C14 C15 178.86(10) . . . . ?
C13 C14 C15 C16 -1.07(18) . . . . ?
C14 C15 C16 F4 -179.62(10) . . . . ?
C14 C15 C16 C17 0.18(19) . . . . ?
F4 C16 C17 C18 -179.28(10) . . . . ?
C15 C16 C17 C18 0.92(18) . . . . ?
C14 C13 C18 C17 0.26(17) . . . . ?
N1 C13 C18 C17 -177.75(10) . . . . ?
C16 C17 C18 C13 -1.12(17) . . . . ?

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
C17 H17 O2 0.95 2.64 3.5157(16) 153.6 3_566
C15 H15 O1 0.95 2.49 3.2670(16) 138.9 2_545
C5 H5B O2 0.99 2.37 3.0605(15) 125.9 4_565

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1427870'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;
_audit_creation_date             2012-04-10
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H16 F3 N O2'
_chemical_formula_sum            'C20 H20 N4 O4 '
_chemical_formula_weight         380.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.474(3)
_cell_length_b                   11.122(2)
_cell_length_c                   14.777(4)
_cell_angle_alpha                68.911(9)
_cell_angle_beta                 89.618(10)
_cell_angle_gamma                83.233(9)
_cell_volume                     1593.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4929
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.5
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16896
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.48
_diffrn_ambient_temperature      113
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
scan:
	Number of images: 90
	           Slice: -110.0000 - 70.0000
	     Image width: 2.0000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0236
	          2theta: -19.9488
scan:
	Number of images: 70
	           Slice: -110.0000 - 30.0000
	     Image width: 2.0000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0236
	          2theta: -19.9488
scan:
	Number of images: 60
	           Slice: -110.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0236
	          2theta: -19.9488
;
_diffrn_measurement_device       
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.058044
_diffrn_orient_matrix_UB_12      -0.075846
_diffrn_orient_matrix_UB_13      -0.011689
_diffrn_orient_matrix_UB_21      -0.004870
_diffrn_orient_matrix_UB_22      0.004035
_diffrn_orient_matrix_UB_23      0.096904
_diffrn_orient_matrix_UB_31      -0.051704
_diffrn_orient_matrix_UB_32      0.040733
_diffrn_orient_matrix_UB_33      -0.030593
_diffrn_radiation_monochromator  Multilayer
_diffrn_radiation_type           Molybdenum
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4618
_reflns_number_total             7492
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.120
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.071
_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)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0890
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25513(15) 0.39039(14) 0.38120(10) 0.0233(4) Uani 1 1 d . . .
H1A H 0.3307 0.4038 0.3397 0.028 Uiso 1 1 calc R . .
H1B H 0.2154 0.3174 0.3744 0.028 Uiso 1 1 calc R . .
C2 C 0.30042(14) 0.35327(14) 0.48577(10) 0.0189(3) Uani 1 1 d . . .
C3 C 0.30889(15) 0.22471(14) 0.54849(10) 0.0229(4) Uani 1 1 d . . .
H3 H 0.2792 0.1618 0.5268 0.027 Uiso 1 1 calc R . .
C4 C 0.36032(16) 0.18673(15) 0.64276(11) 0.0258(4) Uani 1 1 d . . .
H4 H 0.3654 0.0985 0.6850 0.031 Uiso 1 1 calc R . .
C5 C 0.40391(15) 0.27799(15) 0.67460(11) 0.0234(4) Uani 1 1 d . . .
H5 H 0.4396 0.2524 0.7387 0.028 Uiso 1 1 calc R . .
C6 C 0.39545(15) 0.40667(15) 0.61291(11) 0.0231(4) Uani 1 1 d . . .
H6 H 0.4251 0.4694 0.6348 0.028 Uiso 1 1 calc R . .
C7 C 0.34375(15) 0.44397(14) 0.51932(10) 0.0216(3) Uani 1 1 d . . .
H7 H 0.3378 0.5325 0.4776 0.026 Uiso 1 1 calc R . .
C8 C -0.01834(17) 0.38958(15) 0.41515(10) 0.0273(4) Uani 1 1 d . . .
H8A H 0.0357 0.3090 0.4351 0.033 Uiso 1 1 calc R . .
H8B H -0.1074 0.3916 0.4281 0.033 Uiso 1 1 calc R . .
C9 C 0.03084(15) 0.49991(15) 0.36895(10) 0.0197(3) Uani 1 1 d . . .
C10 C -0.05096(15) 0.62835(14) 0.33924(10) 0.0213(4) Uani 1 1 d . . .
H10A H -0.1427 0.6152 0.3379 0.026 Uiso 1 1 calc R . .
H10B H -0.0386 0.6693 0.3875 0.026 Uiso 1 1 calc R . .
C11 C 0.10872(14) 0.74393(14) 0.24686(10) 0.0173(3) Uani 1 1 d . . .
C12 C 0.20665(15) 0.62077(14) 0.28748(10) 0.0185(3) Uani 1 1 d . . .
C13 C 0.13484(16) 0.81150(14) 0.13832(10) 0.0217(4) Uani 1 1 d . . .
C14 C 0.12122(15) 0.83802(13) 0.30039(10) 0.0179(3) Uani 1 1 d . . .
C15 C 0.23976(16) 0.85195(14) 0.33474(10) 0.0238(4) Uani 1 1 d . . .
H15 H 0.3153 0.8008 0.3270 0.029 Uiso 1 1 calc R . .
C16 C 0.24787(17) 0.94085(15) 0.38053(11) 0.0298(4) Uani 1 1 d . . .
H16 H 0.3289 0.9507 0.4037 0.036 Uiso 1 1 calc R . .
C17 C 0.13739(19) 1.01476(16) 0.39212(11) 0.0314(4) Uani 1 1 d . . .
H17 H 0.1428 1.0743 0.4243 0.038 Uiso 1 1 calc R . .
C18 C 0.01970(17) 1.00265(15) 0.35736(11) 0.0288(4) Uani 1 1 d . . .
H18 H -0.0555 1.0543 0.3651 0.035 Uiso 1 1 calc R . .
C19 C 0.01110(16) 0.91462(14) 0.31090(10) 0.0223(4) Uani 1 1 d . . .
H19 H -0.0699 0.9069 0.2864 0.027 Uiso 1 1 calc R . .
N1 N 0.16141(12) 0.50881(11) 0.34583(8) 0.0193(3) Uani 1 1 d . . .
O1 O 0.31974(10) 0.62605(10) 0.26763(7) 0.0254(3) Uani 1 1 d . . .
O2 O -0.01846(10) 0.71318(9) 0.24481(7) 0.0199(2) Uani 1 1 d . . .
F1 F 0.03944(9) 0.90668(8) 0.09502(6) 0.0288(2) Uani 1 1 d . . .
F2 F 0.24343(9) 0.86648(8) 0.12417(6) 0.0282(2) Uani 1 1 d . . .
F3 F 0.14194(9) 0.72930(8) 0.09032(6) 0.0294(2) Uani 1 1 d . . .
C20 C 0.79134(16) 0.56799(15) 0.14199(10) 0.0239(4) Uani 1 1 d . . .
H20A H 0.8687 0.5173 0.1818 0.029 Uiso 1 1 calc R . .
H20B H 0.7669 0.6442 0.1609 0.029 Uiso 1 1 calc R . .
C21 C 0.82471(14) 0.61520(14) 0.03566(11) 0.0207(3) Uani 1 1 d . . .
C22 C 0.84997(16) 0.74212(15) -0.01109(11) 0.0279(4) Uani 1 1 d . . .
H22 H 0.8429 0.8003 0.0230 0.033 Uiso 1 1 calc R . .
C23 C 0.88554(17) 0.78523(16) -0.10721(12) 0.0337(4) Uani 1 1 d . . .
H23 H 0.9026 0.8724 -0.1383 0.040 Uiso 1 1 calc R . .
C24 C 0.89609(16) 0.70141(16) -0.15757(11) 0.0289(4) Uani 1 1 d . . .
H24 H 0.9204 0.7305 -0.2233 0.035 Uiso 1 1 calc R . .
C25 C 0.87101(16) 0.57527(16) -0.11164(11) 0.0260(4) Uani 1 1 d . . .
H25 H 0.8782 0.5174 -0.1460 0.031 Uiso 1 1 calc R . .
C26 C 0.83538(15) 0.53183(15) -0.01569(11) 0.0236(4) Uani 1 1 d . . .
H26 H 0.8182 0.4446 0.0150 0.028 Uiso 1 1 calc R . .
C27 C 0.53025(16) 0.67266(14) 0.07808(10) 0.0259(4) Uani 1 1 d . . .
H27A H 0.5950 0.7290 0.0663 0.031 Uiso 1 1 calc R . .
H27B H 0.4442 0.7068 0.0552 0.031 Uiso 1 1 calc R . .
C28 C 0.56012(15) 0.54604(14) 0.12668(10) 0.0184(3) Uani 1 1 d . . .
C29 C 0.46244(15) 0.45382(14) 0.14314(10) 0.0218(3) Uani 1 1 d . . .
H29A H 0.3751 0.5022 0.1356 0.026 Uiso 1 1 calc R . .
H29B H 0.4702 0.4126 0.0938 0.026 Uiso 1 1 calc R . .
C30 C 0.59991(15) 0.27792(14) 0.24981(10) 0.0181(3) Uani 1 1 d . . .
C31 C 0.71244(15) 0.35962(14) 0.22405(10) 0.0188(3) Uani 1 1 d . . .
C32 C 0.60879(17) 0.19955(15) 0.35984(11) 0.0248(4) Uani 1 1 d . . .
C33 C 0.60224(15) 0.18417(13) 0.19394(10) 0.0180(3) Uani 1 1 d . . .
C34 C 0.71608(16) 0.13978(14) 0.16008(10) 0.0225(4) Uani 1 1 d . . .
H34 H 0.7946 0.1698 0.1690 0.027 Uiso 1 1 calc R . .
C35 C 0.71455(17) 0.05177(15) 0.11330(11) 0.0282(4) Uani 1 1 d . . .
H35 H 0.7920 0.0217 0.0901 0.034 Uiso 1 1 calc R . .
C36 C 0.60037(19) 0.00779(15) 0.10044(11) 0.0313(4) Uani 1 1 d . . .
H36 H 0.5998 -0.0530 0.0688 0.038 Uiso 1 1 calc R . .
C37 C 0.48671(18) 0.05190(15) 0.13341(11) 0.0292(4) Uani 1 1 d . . .
H37 H 0.4084 0.0219 0.1241 0.035 Uiso 1 1 calc R . .
C38 C 0.48768(16) 0.14036(14) 0.18021(10) 0.0238(4) Uani 1 1 d . . .
H38 H 0.4099 0.1708 0.2028 0.029 Uiso 1 1 calc R . .
N2 N 0.68579(12) 0.48703(11) 0.16340(8) 0.0185(3) Uani 1 1 d . . .
O3 O 0.82040(11) 0.31004(10) 0.25711(8) 0.0282(3) Uani 1 1 d . . .
O4 O 0.47922(10) 0.35531(9) 0.23804(7) 0.0218(2) Uani 1 1 d . . .
F4 F 0.70676(9) 0.10391(8) 0.38580(6) 0.0297(2) Uani 1 1 d . . .
F5 F 0.50142(10) 0.14374(9) 0.38895(6) 0.0340(2) Uani 1 1 d . . .
F6 F 0.62249(10) 0.27535(8) 0.41091(6) 0.0349(3) 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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.513(2) . ?
C1 N1 1.4758(18) . ?
C2 C3 1.389(2) . ?
C2 C7 1.3929(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C8 C9 1.334(2) . ?
C9 C10 1.494(2) . ?
C9 N1 1.4135(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 O2 1.4405(16) . ?
C11 C12 1.541(2) . ?
C11 C13 1.5451(19) . ?
C11 C14 1.5385(19) . ?
C11 O2 1.4169(17) . ?
C12 N1 1.3710(18) . ?
C12 O1 1.2214(18) . ?
C13 F1 1.3417(17) . ?
C13 F2 1.3341(17) . ?
C13 F3 1.3396(15) . ?
C14 C15 1.390(2) . ?
C14 C19 1.393(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.395(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.519(2) . ?
C20 N2 1.4690(18) . ?
C21 C22 1.387(2) . ?
C21 C26 1.3888(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.377(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.388(2) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9500 . ?
C27 H27B 0.9500 . ?
C27 C28 1.330(2) . ?
C28 C29 1.491(2) . ?
C28 N2 1.4168(19) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 O4 1.4318(17) . ?
C30 C31 1.535(2) . ?
C30 C32 1.541(2) . ?
C30 C33 1.5435(18) . ?
C30 O4 1.4170(17) . ?
C31 N2 1.3731(18) . ?
C31 O3 1.2198(18) . ?
C32 F4 1.3363(18) . ?
C32 F5 1.3420(18) . ?
C32 F6 1.3374(16) . ?
C33 C34 1.395(2) . ?
C33 C38 1.389(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.3883(19) . ?
C35 H35 0.9500 . ?
C35 C36 1.383(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.386(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.392(2) . ?
C38 H38 0.9500 . ?

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
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
N1 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
N1 C1 C2 113.71(11) . . ?
C3 C2 C1 120.03(13) . . ?
C3 C2 C7 118.54(13) . . ?
C7 C2 C1 121.23(13) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.91(14) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.76(14) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.90(14) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.08(14) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.80(14) . . ?
C6 C7 H7 119.6 . . ?
H8A C8 H8B 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C9 C8 H8B 120.0 . . ?
C8 C9 C10 121.19(15) . . ?
C8 C9 N1 124.96(15) . . ?
N1 C9 C10 113.83(13) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O2 C10 C9 111.00(12) . . ?
O2 C10 H10A 109.4 . . ?
O2 C10 H10B 109.4 . . ?
C12 C11 C13 107.65(11) . . ?
C14 C11 C12 111.71(12) . . ?
C14 C11 C13 109.44(11) . . ?
O2 C11 C12 111.68(12) . . ?
O2 C11 C13 103.16(11) . . ?
O2 C11 C14 112.71(12) . . ?
N1 C12 C11 117.44(13) . . ?
O1 C12 C11 119.76(14) . . ?
O1 C12 N1 122.80(14) . . ?
F1 C13 C11 110.31(12) . . ?
F2 C13 C11 112.97(12) . . ?
F2 C13 F1 106.53(12) . . ?
F2 C13 F3 107.45(12) . . ?
F3 C13 C11 112.19(12) . . ?
F3 C13 F1 107.04(12) . . ?
C15 C14 C11 121.69(13) . . ?
C15 C14 C19 119.56(14) . . ?
C19 C14 C11 118.69(14) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.10(15) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.79(16) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.51(15) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.96(16) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.06(16) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C9 N1 C1 119.14(13) . . ?
C12 N1 C1 116.93(13) . . ?
C12 N1 C9 123.84(13) . . ?
C11 O2 C10 110.71(10) . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
N2 C20 H20A 108.9 . . ?
N2 C20 H20B 108.9 . . ?
N2 C20 C21 113.23(11) . . ?
C22 C21 C20 120.22(13) . . ?
C22 C21 C26 118.60(14) . . ?
C26 C21 C20 121.13(13) . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.87(14) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.05(15) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.40(15) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.74(14) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.34(15) . . ?
C25 C26 H26 119.8 . . ?
H27A C27 H27B 120.0 . . ?
C28 C27 H27A 120.0 . . ?
C28 C27 H27B 120.0 . . ?
C27 C28 C29 121.59(15) . . ?
C27 C28 N2 123.72(15) . . ?
N2 C28 C29 114.64(12) . . ?
C28 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
O4 C29 C28 111.24(12) . . ?
O4 C29 H29A 109.4 . . ?
O4 C29 H29B 109.4 . . ?
C31 C30 C32 108.45(12) . . ?
C31 C30 C33 111.80(12) . . ?
C32 C30 C33 109.56(11) . . ?
O4 C30 C31 112.43(12) . . ?
O4 C30 C32 102.35(11) . . ?
O4 C30 C33 111.76(12) . . ?
N2 C31 C30 117.50(13) . . ?
O3 C31 C30 119.64(13) . . ?
O3 C31 N2 122.86(14) . . ?
F4 C32 C30 112.80(12) . . ?
F4 C32 F5 106.62(12) . . ?
F4 C32 F6 107.69(13) . . ?
F5 C32 C30 110.80(13) . . ?
F6 C32 C30 111.60(12) . . ?
F6 C32 F5 107.03(12) . . ?
C34 C33 C30 121.86(14) . . ?
C38 C33 C30 118.39(13) . . ?
C38 C33 C34 119.72(13) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 119.95(15) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.08(16) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.8 . . ?
C35 C36 C37 120.35(15) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.1 . . ?
C36 C37 C38 119.80(16) . . ?
C38 C37 H37 120.1 . . ?
C33 C38 C37 120.10(15) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C28 N2 C20 118.67(12) . . ?
C31 N2 C20 118.04(13) . . ?
C31 N2 C28 123.12(13) . . ?
C30 O4 C29 111.30(11) . . ?

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
C1 C2 C3 C4 174.68(14) . . . . ?
C1 C2 C7 C6 -174.37(14) . . . . ?
C2 C1 N1 C9 -80.54(17) . . . . ?
C2 C1 N1 C12 102.79(15) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C2 C7 C6 0.7(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C2 -0.4(2) . . . . ?
C7 C2 C3 C4 -0.4(2) . . . . ?
C8 C9 C10 O2 -140.35(13) . . . . ?
C8 C9 N1 C1 -5.3(2) . . . . ?
C8 C9 N1 C12 171.14(13) . . . . ?
C9 C10 O2 C11 -64.80(15) . . . . ?
C10 C9 N1 C1 173.05(11) . . . . ?
C10 C9 N1 C12 -10.54(19) . . . . ?
C11 C12 N1 C1 177.71(11) . . . . ?
C11 C12 N1 C9 1.21(19) . . . . ?
C11 C14 C15 C16 178.20(13) . . . . ?
C11 C14 C19 C18 -178.74(13) . . . . ?
C12 C11 C13 F1 169.50(12) . . . . ?
C12 C11 C13 F2 -71.40(15) . . . . ?
C12 C11 C13 F3 50.25(16) . . . . ?
C12 C11 C14 C15 34.71(19) . . . . ?
C12 C11 C14 C19 -147.92(13) . . . . ?
C12 C11 O2 C10 54.21(14) . . . . ?
C13 C11 C12 N1 -135.42(12) . . . . ?
C13 C11 C12 O1 45.04(18) . . . . ?
C13 C11 C14 C15 -84.41(16) . . . . ?
C13 C11 C14 C19 92.96(16) . . . . ?
C13 C11 O2 C10 169.55(10) . . . . ?
C14 C11 C12 N1 104.41(15) . . . . ?
C14 C11 C12 O1 -75.13(16) . . . . ?
C14 C11 C13 F1 -68.90(15) . . . . ?
C14 C11 C13 F2 50.20(16) . . . . ?
C14 C11 C13 F3 171.85(13) . . . . ?
C14 C11 O2 C10 -72.52(14) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C15 C14 C19 C18 -1.3(2) . . . . ?
C15 C16 C17 C18 -1.0(2) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C17 C18 C19 C14 0.6(2) . . . . ?
C19 C14 C15 C16 0.9(2) . . . . ?
N1 C1 C2 C3 135.62(15) . . . . ?
N1 C1 C2 C7 -49.4(2) . . . . ?
N1 C9 C10 O2 41.25(17) . . . . ?
O1 C12 N1 C1 -2.8(2) . . . . ?
O1 C12 N1 C9 -179.26(13) . . . . ?
O2 C11 C12 N1 -22.86(16) . . . . ?
O2 C11 C12 O1 157.60(12) . . . . ?
O2 C11 C13 F1 51.30(14) . . . . ?
O2 C11 C13 F2 170.40(11) . . . . ?
O2 C11 C13 F3 -67.95(14) . . . . ?
O2 C11 C14 C15 161.42(13) . . . . ?
O2 C11 C14 C19 -21.21(18) . . . . ?
C20 C21 C22 C23 177.45(15) . . . . ?
C20 C21 C26 C25 -177.39(14) . . . . ?
C21 C20 N2 C28 -68.75(16) . . . . ?
C21 C20 N2 C31 115.90(14) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C21 C26 C25 0.2(2) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
C24 C25 C26 C21 -0.1(2) . . . . ?
C26 C21 C22 C23 -0.2(2) . . . . ?
C27 C28 C29 O4 -141.56(13) . . . . ?
C27 C28 N2 C20 -3.87(19) . . . . ?
C27 C28 N2 C31 171.23(13) . . . . ?
C28 C29 O4 C30 -62.97(14) . . . . ?
C29 C28 N2 C20 173.76(11) . . . . ?
C29 C28 N2 C31 -11.14(18) . . . . ?
C30 C31 N2 C20 177.06(11) . . . . ?
C30 C31 N2 C28 1.94(19) . . . . ?
C30 C33 C34 C35 177.62(13) . . . . ?
C30 C33 C38 C37 -177.57(13) . . . . ?
C31 C30 C32 F4 -71.07(15) . . . . ?
C31 C30 C32 F5 169.48(11) . . . . ?
C31 C30 C32 F6 50.32(17) . . . . ?
C31 C30 C33 C34 25.61(19) . . . . ?
C31 C30 C33 C38 -156.45(13) . . . . ?
C31 C30 O4 C29 52.93(14) . . . . ?
C32 C30 C31 N2 -134.97(13) . . . . ?
C32 C30 C31 O3 45.35(17) . . . . ?
C32 C30 C33 C34 -94.65(16) . . . . ?
C32 C30 C33 C38 83.29(16) . . . . ?
C32 C30 O4 C29 169.09(11) . . . . ?
C33 C30 C31 N2 104.12(14) . . . . ?
C33 C30 C31 O3 -75.56(16) . . . . ?
C33 C30 C32 F4 51.21(17) . . . . ?
C33 C30 C32 F5 -68.23(16) . . . . ?
C33 C30 C32 F6 172.60(13) . . . . ?
C33 C30 O4 C29 -73.76(14) . . . . ?
C33 C34 C35 C36 -0.2(2) . . . . ?
C34 C33 C38 C37 0.4(2) . . . . ?
C34 C35 C36 C37 0.5(2) . . . . ?
C35 C36 C37 C38 -0.4(2) . . . . ?
C36 C37 C38 C33 -0.1(2) . . . . ?
C38 C33 C34 C35 -0.3(2) . . . . ?
N2 C20 C21 C22 137.85(15) . . . . ?
N2 C20 C21 C26 -44.6(2) . . . . ?
N2 C28 C29 O4 40.75(16) . . . . ?
O3 C31 N2 C20 -3.3(2) . . . . ?
O3 C31 N2 C28 -178.39(13) . . . . ?
O4 C30 C31 N2 -22.53(17) . . . . ?
O4 C30 C31 O3 157.79(12) . . . . ?
O4 C30 C32 F4 169.93(12) . . . . ?
O4 C30 C32 F5 50.48(14) . . . . ?
O4 C30 C32 F6 -68.68(15) . . . . ?
O4 C30 C33 C34 152.64(13) . . . . ?
O4 C30 C33 C38 -29.43(17) . . . . ?

