# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_H-toluene
_database_code_depnum_ccdc_archive 'CCDC 1557862'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H21 N3 O6, C7 H8'
_chemical_formula_sum            'C40 H29 N3 O6'
_chemical_formula_weight         647.66

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.400(3)
_cell_length_b                   11.400(3)
_cell_length_c                   42.6593(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4801.2(18)
_cell_formula_units_Z            6
_cell_measurement_temperature    263(2)
_cell_measurement_reflns_used    3874
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      30.2

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2028
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      263(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14110
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.45
_reflns_number_total             1981
_reflns_number_gt                1668
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0463P)²+22.4533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1981
_refine_ls_number_parameters     178
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2242
_refine_ls_wR_factor_gt          0.2178
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_restrained_S_all      1.273
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7444(4) 0.4749(4) 0.13414(8) 0.0397(8) Uani 1 1 d . . .
C2 C 0.8080(4) 0.3962(4) 0.13417(8) 0.0400(8) Uani 1 1 d . . .
C3 C 0.9582(4) 0.4905(4) 0.13141(8) 0.0465(9) Uani 1 1 d . . .
N1 N 0.9756(3) 0.6209(3) 0.12902(7) 0.0504(8) Uani 1 1 d . . .
C4 C 0.8540(4) 0.6218(4) 0.13143(8) 0.0460(9) Uani 1 1 d . . .
O1 O 1.0492(3) 0.4653(3) 0.13107(7) 0.0626(9) Uani 1 1 d . . .
O2 O 0.8442(3) 0.7225(3) 0.13136(7) 0.0591(8) Uani 1 1 d . . .
C5 C 1.1076(4) 0.7444(4) 0.12353(10) 0.0596(12) Uani 1 1 d . . .
H5 H 1.1796 0.7310 0.1316 0.072 Uiso 1 1 calc R . .
H5A H 1.1104 0.8198 0.1347 0.072 Uiso 1 1 calc R . .
C6 C 1.1306(4) 0.7777(5) 0.08904(10) 0.0566(11) Uani 1 1 d . . .
C7 C 1.1607(5) 0.7012(6) 0.06879(12) 0.0756(14) Uani 1 1 d . . .
H7 H 1.1679 0.6289 0.0766 0.091 Uiso 1 1 calc R . .
C8 C 1.1802(6) 0.7307(7) 0.03717(13) 0.0867(17) Uani 1 1 d . . .
H8 H 1.1997 0.6781 0.0239 0.104 Uiso 1 1 calc R . .
C9 C 1.1708(6) 0.8377(7) 0.02540(13) 0.0896(18) Uani 1 1 d . . .
H9 H 1.1849 0.8583 0.0041 0.108 Uiso 1 1 calc R . .
C10 C 1.1407(7) 0.9138(7) 0.04492(14) 0.0968(19) Uani 1 1 d . . .
H10 H 1.1330 0.9856 0.0369 0.116 Uiso 1 1 calc R . .
C11 C 1.1214(6) 0.8844(6) 0.07689(12) 0.0773(15) Uani 1 1 d . . .
H11 H 1.1021 0.9375 0.0901 0.093 Uiso 1 1 calc R . .
C12 C 0.477(3) 0.108(3) 0.0505(8) 0.133(9) Uani 0.33 1 d PU A -1
H12 H 0.3891 0.1007 0.0506 0.200 Uiso 0.33 1 calc PR A -1
H12A H 0.4861 0.0638 0.0686 0.200 Uiso 0.33 1 calc PR A -1
H12B H 0.4869 0.0670 0.0318 0.200 Uiso 0.33 1 calc PR A -1
C13 C 0.580(4) 0.2495(17) 0.0510(3) 0.078(5) Uani 0.33 1 d PGU A -1
C14 C 0.714(4) 0.2783(19) 0.0515(3) 0.082(5) Uani 0.33 1 d PGU A -1
H14 H 0.7329 0.2081 0.0514 0.098 Uiso 0.33 1 calc PR A -1
C15 C 0.819(4) 0.412(2) 0.0521(4) 0.086(6) Uani 0.33 1 d PGU A -1
H15 H 0.9080 0.4313 0.0524 0.103 Uiso 0.33 1 calc PR A -1
C16 C 0.790(5) 0.5169(16) 0.0523(4) 0.099(6) Uani 0.33 1 d PGU A -1
H16 H 0.8600 0.6064 0.0527 0.119 Uiso 0.33 1 calc PR A -1
C17 C 0.656(5) 0.488(2) 0.0518(4) 0.093(7) Uani 0.33 1 d PGU A -1
H17 H 0.6367 0.5584 0.0519 0.111 Uiso 0.33 1 calc PR A -1
C18 C 0.551(5) 0.354(3) 0.0512(5) 0.085(6) Uani 0.33 1 d PGU A -1
H18 H 0.4616 0.3352 0.0509 0.102 Uiso 0.33 1 calc PR A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.390(5) 2_655 ?
C1 C2 1.408(5) . ?
C1 C4 1.512(5) . ?
C2 C1 1.390(5) 3_665 ?
C2 C3 1.504(5) . ?
C3 O1 1.206(5) . ?
C3 N1 1.402(5) . ?
N1 C4 1.395(5) . ?
N1 C5 1.478(5) . ?
C4 O2 1.208(5) . ?
C5 C6 1.509(6) . ?
C5 H5 0.9700 . ?
C5 H5A 0.9700 . ?
C6 C11 1.373(7) . ?
C6 C7 1.387(7) . ?
C7 C8 1.381(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.395(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.44(4) . ?
C12 H12 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 H18 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
C2 C1 C2 119.9(4) 2_655 . ?
C2 C1 C4 132.3(3) 2_655 . ?
C2 C1 C4 107.6(3) . . ?
C1 C2 C1 120.1(4) 3_665 . ?
C1 C2 C3 131.6(3) 3_665 . ?
C1 C2 C3 108.0(3) . . ?
O1 C3 N1 124.7(4) . . ?
O1 C3 C2 129.7(4) . . ?
N1 C3 C2 105.7(3) . . ?
C4 N1 C3 112.9(3) . . ?
C4 N1 C5 123.2(4) . . ?
C3 N1 C5 123.9(3) . . ?
O2 C4 N1 124.9(4) . . ?
O2 C4 C1 129.4(4) . . ?
N1 C4 C1 105.7(3) . . ?
N1 C5 C6 111.1(3) . . ?
N1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
H5 C5 H5A 108.0 . . ?
C11 C6 C7 118.3(4) . . ?
C11 C6 C5 120.7(4) . . ?
C7 C6 C5 121.0(5) . . ?
C8 C7 C6 121.0(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 120.0(6) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.2(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 120.6(5) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 H12 109.5 . . ?
C13 C12 H12A 109.5 . . ?
H12 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C12 117(2) . . ?
C18 C13 C12 123(2) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?

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
C2 C1 C2 C1 0.2(7) 2_655 . . 3_665 ?
C4 C1 C2 C1 -175.3(3) . . . 3_665 ?
C2 C1 C2 C3 175.3(3) 2_655 . . . ?
C4 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 O1 -6.9(7) 3_665 . . . ?
C1 C2 C3 O1 178.7(4) . . . . ?
C1 C2 C3 N1 172.9(4) 3_665 . . . ?
C1 C2 C3 N1 -1.5(4) . . . . ?
O1 C3 N1 C4 -177.3(4) . . . . ?
C2 C3 N1 C4 2.9(4) . . . . ?
O1 C3 N1 C5 4.5(6) . . . . ?
C2 C3 N1 C5 -175.3(3) . . . . ?
C3 N1 C4 O2 176.8(4) . . . . ?
C5 N1 C4 O2 -5.0(6) . . . . ?
C3 N1 C4 C1 -2.9(4) . . . . ?
C5 N1 C4 C1 175.2(3) . . . . ?
C2 C1 C4 O2 7.4(7) 2_655 . . . ?
C2 C1 C4 O2 -177.9(4) . . . . ?
C2 C1 C4 N1 -172.9(4) 2_655 . . . ?
C2 C1 C4 N1 1.8(4) . . . . ?
C4 N1 C5 C6 -84.2(5) . . . . ?
C3 N1 C5 C6 93.8(5) . . . . ?
N1 C5 C6 C11 106.5(5) . . . . ?
N1 C5 C6 C7 -73.2(5) . . . . ?
C11 C6 C7 C8 -0.4(8) . . . . ?
C5 C6 C7 C8 179.3(5) . . . . ?
C6 C7 C8 C9 0.5(9) . . . . ?
C7 C8 C9 C10 -0.7(10) . . . . ?
C8 C9 C10 C11 0.9(10) . . . . ?
C7 C6 C11 C10 0.6(8) . . . . ?
C5 C6 C11 C10 -179.1(5) . . . . ?
C9 C10 C11 C6 -0.9(9) . . . . ?
C18 C13 C14 C15 0.0 . . . . ?
C12 C13 C14 C15 -180(2) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C12 C13 C18 C17 180(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.45
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_F-Benzene
_database_code_depnum_ccdc_archive 'CCDC 1557868'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H18 F3 N3 O6, C6 H6'
_chemical_formula_sum            'C39 H24 F3 N3 O6'
_chemical_formula_weight         687.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R -3'
_symmetry_space_group_name_Hall  '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.1835(5)
_cell_length_b                   11.1835(5)
_cell_length_c                   44.034(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4769.5(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    4480
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      30.2

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2124
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         24771
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17900
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1866
_reflns_number_gt                1681
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0687P)²+0.8276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1866
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.64301(11) 0.62300(11) 0.13032(2) 0.0214(3) Uani 1 1 d . . .
C1 C 0.76786(14) 0.62520(13) 0.13316(3) 0.0198(3) Uani 1 1 d . . .
C2 C 0.73068(13) 0.47694(13) 0.13630(3) 0.0184(3) Uani 1 1 d . . .
C3 C 0.58600(13) 0.39598(13) 0.13632(3) 0.0183(3) Uani 1 1 d . . .
C4 C 0.52869(14) 0.49096(13) 0.13293(3) 0.0208(3) Uani 1 1 d . . .
O1 O 0.88023(10) 0.72878(9) 0.13302(2) 0.0252(3) Uani 1 1 d . . .
O2 O 0.40978(10) 0.46402(10) 0.13225(2) 0.0291(3) Uani 1 1 d . . .
C5 C 0.63254(15) 0.74667(14) 0.12431(3) 0.0248(3) Uani 1 1 d . . .
H5 H 0.7068 0.8262 0.1354 0.030 Uiso 1 1 calc R . .
H5A H 0.5428 0.7317 0.1319 0.030 Uiso 1 1 calc R . .
C6 C 0.64440(14) 0.77954(14) 0.09068(3) 0.0237(3) Uani 1 1 d . . .
C7 C 0.76015(16) 0.89545(15) 0.07943(3) 0.0285(4) Uani 1 1 d . . .
H7 H 0.8320 0.9540 0.0929 0.034 Uiso 1 1 calc R . .
C8 C 0.77245(17) 0.92716(17) 0.04866(3) 0.0338(4) Uani 1 1 d . . .
H8 H 0.8512 1.0071 0.0410 0.041 Uiso 1 1 calc R . .
C9 C 0.66727(17) 0.83945(17) 0.02964(3) 0.0329(4) Uani 1 1 d . . .
C10 C 0.55129(16) 0.72322(17) 0.03978(3) 0.0348(4) Uani 1 1 d . . .
H10 H 0.4807 0.6644 0.0260 0.042 Uiso 1 1 calc R . .
C11 C 0.53985(16) 0.69394(16) 0.07064(3) 0.0300(4) Uani 1 1 d . . .
H11 H 0.4599 0.6147 0.0782 0.036 Uiso 1 1 calc R . .
C12 C 0.8026(2) 0.4395(2) 0.05621(4) 0.0479(5) Uani 1 1 d . . .
H12 H 0.8958 0.5124 0.0563 0.057 Uiso 1 1 calc R . .
C13 C 0.6962(2) 0.4692(2) 0.05617(4) 0.0479(5) Uani 1 1 d . . .
H13 H 0.7166 0.5625 0.0561 0.058 Uiso 1 1 calc R . .
F1 F 0.67864(11) 0.86964(11) -0.000470(19) 0.0477(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
N1 C1 1.3897(17) . ?
N1 C4 1.3929(17) . ?
N1 C5 1.4693(16) . ?
C1 O1 1.2105(16) . ?
C1 C2 1.5006(17) . ?
C2 C3 1.3806(18) 3_665 ?
C2 C3 1.4046(18) . ?
C3 C2 1.3807(18) 2_655 ?
C3 C4 1.4973(17) . ?
C4 O2 1.2081(16) . ?
C5 C6 1.5156(18) . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C7 1.387(2) . ?
C6 C11 1.394(2) . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(2) . ?
C8 H8 0.9500 . ?
C9 F1 1.3582(17) . ?
C9 C10 1.373(2) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) 3_665 ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C12 1.383(3) 2_655 ?
C13 H13 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
C1 N1 C4 113.13(10) . . ?
C1 N1 C5 123.49(11) . . ?
C4 N1 C5 123.36(11) . . ?
O1 C1 N1 124.73(12) . . ?
O1 C1 C2 129.74(12) . . ?
N1 C1 C2 105.53(11) . . ?
C3 C2 C3 119.86(13) 3_665 . ?
C3 C2 C1 132.04(12) 3_665 . ?
C3 C2 C1 107.81(11) . . ?
C2 C3 C2 120.14(13) 2_655 . ?
C2 C3 C4 131.67(12) 2_655 . ?
C2 C3 C4 107.84(11) . . ?
O2 C4 N1 125.08(12) . . ?
O2 C4 C3 129.33(12) . . ?
N1 C4 C3 105.59(11) . . ?
N1 C5 C6 111.46(11) . . ?
N1 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
N1 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
H5 C5 H5A 108.0 . . ?
C7 C6 C11 119.08(14) . . ?
C7 C6 C5 120.22(13) . . ?
C11 C6 C5 120.70(13) . . ?
C6 C7 C8 120.92(14) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 118.11(15) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
F1 C9 C10 118.65(14) . . ?
F1 C9 C8 118.46(15) . . ?
C10 C9 C8 122.89(14) . . ?
C9 C10 C11 118.27(14) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C6 120.72(14) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C13 C12 C13 120.0(2) 3_665 . ?
C13 C12 H12 120.0 3_665 . ?
C13 C12 H12 120.0 . . ?
C12 C13 C12 120.0(2) 2_655 . ?
C12 C13 H13 120.0 2_655 . ?
C12 C13 H13 120.0 . . ?

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
C4 N1 C1 O1 -176.58(12) . . . . ?
C5 N1 C1 O1 5.1(2) . . . . ?
C4 N1 C1 C2 3.31(14) . . . . ?
C5 N1 C1 C2 -175.03(11) . . . . ?
O1 C1 C2 C3 -8.7(2) . . . 3_665 ?
N1 C1 C2 C3 171.38(13) . . . 3_665 ?
O1 C1 C2 C3 177.64(13) . . . . ?
N1 C1 C2 C3 -2.24(14) . . . . ?
C3 C2 C3 C2 -0.1(2) 3_665 . . 2_655 ?
C1 C2 C3 C2 174.39(9) . . . 2_655 ?
C3 C2 C3 C4 -174.04(9) 3_665 . . . ?
C1 C2 C3 C4 0.50(14) . . . . ?
C1 N1 C4 O2 177.39(12) . . . . ?
C5 N1 C4 O2 -4.3(2) . . . . ?
C1 N1 C4 C3 -3.01(14) . . . . ?
C5 N1 C4 C3 175.32(11) . . . . ?
C2 C3 C4 O2 8.1(2) 2_655 . . . ?
C2 C3 C4 O2 -179.01(13) . . . . ?
C2 C3 C4 N1 -171.51(13) 2_655 . . . ?
C2 C3 C4 N1 1.42(14) . . . . ?
C1 N1 C5 C6 83.82(15) . . . . ?
C4 N1 C5 C6 -94.35(15) . . . . ?
N1 C5 C6 C7 -110.65(14) . . . . ?
N1 C5 C6 C11 69.14(16) . . . . ?
C11 C6 C7 C8 0.3(2) . . . . ?
C5 C6 C7 C8 -179.87(13) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 F1 -179.90(13) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
F1 C9 C10 C11 -179.33(13) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C6 -0.8(2) . . . . ?
C7 C6 C11 C10 0.5(2) . . . . ?
C5 C6 C11 C10 -179.33(13) . . . . ?
C13 C12 C13 C12 0.2(3) 3_665 . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_H-orange
_database_code_depnum_ccdc_archive 'CCDC 1557860'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H21 N3 O6'
_chemical_formula_sum            'C33 H21 N3 O6'
_chemical_formula_weight         555.53

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.2424(18)
_cell_length_b                   13.5392(17)
_cell_length_c                   26.421(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.0247(17)
_cell_angle_gamma                90.00
_cell_volume                     5094.0(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    93
_cell_measurement_reflns_used    17453
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      31.2

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2304
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            83005
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.50
_reflns_number_total             11674
_reflns_number_gt                10447
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+1.9594P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11674
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.53547(8) 0.57698(9) 0.05147(4) 0.0181(2) Uani 1 1 d . . .
C2 C 0.47112(9) 0.66377(9) 0.04457(4) 0.0196(2) Uani 1 1 d . . .
N1 N 0.51703(8) 0.72799(8) 0.01214(4) 0.0207(2) Uani 1 1 d . . .
C3 C 0.60017(9) 0.68864(9) -0.00665(4) 0.0204(2) Uani 1 1 d . . .
C4 C 0.61263(8) 0.59075(9) 0.01981(4) 0.0183(2) Uani 1 1 d . . .
O1 O 0.39362(6) 0.67660(7) 0.06094(3) 0.02476(19) Uani 1 1 d . . .
O2 O 0.64805(7) 0.72632(7) -0.03846(4) 0.0276(2) Uani 1 1 d . . .
C5 C 0.68035(8) 0.51794(9) 0.01649(4) 0.0180(2) Uani 1 1 d . . .
C6 C 0.76943(9) 0.51170(9) -0.01288(4) 0.0198(2) Uani 1 1 d . . .
N2 N 0.80842(7) 0.42050(7) -0.00050(4) 0.0194(2) Uani 1 1 d . . .
C7 C 0.75456(8) 0.36567(9) 0.03269(4) 0.0187(2) Uani 1 1 d . . .
C8 C 0.67114(8) 0.42984(9) 0.04405(4) 0.0176(2) Uani 1 1 d . . .
O3 O 0.80228(7) 0.57074(7) -0.04162(4) 0.0280(2) Uani 1 1 d . . .
O4 O 0.77373(6) 0.28451(7) 0.04838(3) 0.02397(19) Uani 1 1 d . . .
C9 C 0.59527(8) 0.41678(9) 0.07541(4) 0.0176(2) Uani 1 1 d . . .
C10 C 0.56569(8) 0.33184(9) 0.10833(4) 0.0181(2) Uani 1 1 d . . .
N3 N 0.48568(7) 0.36385(8) 0.13281(4) 0.0191(2) Uani 1 1 d . . .
C11 C 0.45512(9) 0.45749(9) 0.11668(5) 0.0200(2) Uani 1 1 d . . .
C12 C 0.52749(8) 0.49136(9) 0.07966(4) 0.0182(2) Uani 1 1 d . . .
O5 O 0.59985(6) 0.25069(6) 0.11207(3) 0.02092(18) Uani 1 1 d . . .
O6 O 0.38506(7) 0.49853(7) 0.12998(4) 0.0278(2) Uani 1 1 d . . .
C13 C 0.47625(10) 0.82347(9) -0.00370(5) 0.0237(3) Uani 1 1 d . . .
H13 H 0.4138 0.8120 -0.0196 0.028 Uiso 1 1 calc R . .
H13A H 0.5169 0.8542 -0.0293 0.028 Uiso 1 1 calc R . .
C14 C 0.46627(9) 0.89300(9) 0.04054(5) 0.0218(2) Uani 1 1 d . . .
C15 C 0.37870(10) 0.90971(10) 0.06112(5) 0.0284(3) Uani 1 1 d . . .
H15 H 0.3250 0.8766 0.0476 0.034 Uiso 1 1 calc R . .
C16 C 0.36924(11) 0.97467(11) 0.10146(6) 0.0326(3) Uani 1 1 d . . .
H16 H 0.3091 0.9864 0.1152 0.039 Uiso 1 1 calc R . .
C17 C 0.44722(11) 1.02208(10) 0.12150(5) 0.0304(3) Uani 1 1 d . . .
H17 H 0.4407 1.0659 0.1493 0.036 Uiso 1 1 calc R . .
C18 C 0.53500(10) 1.00603(10) 0.10127(5) 0.0276(3) Uani 1 1 d . . .
H18 H 0.5885 1.0389 0.1151 0.033 Uiso 1 1 calc R . .
C19 C 0.54447(9) 0.94173(9) 0.06072(5) 0.0241(3) Uani 1 1 d . . .
H19 H 0.6046 0.9310 0.0467 0.029 Uiso 1 1 calc R . .
C20 C 0.89750(9) 0.38523(10) -0.02025(5) 0.0219(2) Uani 1 1 d . . .
H20 H 0.9369 0.3593 0.0080 0.026 Uiso 1 1 calc R . .
H20A H 0.9314 0.4412 -0.0357 0.026 Uiso 1 1 calc R . .
C21 C 0.88291(9) 0.30498(9) -0.05940(5) 0.0208(2) Uani 1 1 d . . .
C22 C 0.81122(9) 0.31185(10) -0.09580(5) 0.0249(3) Uani 1 1 d . . .
H22 H 0.7717 0.3684 -0.0968 0.030 Uiso 1 1 calc R . .
C23 C 0.79741(10) 0.23620(12) -0.13065(6) 0.0334(3) Uani 1 1 d . . .
H23 H 0.7475 0.2404 -0.1549 0.040 Uiso 1 1 calc R . .
C24 C 0.85612(11) 0.15457(11) -0.13020(6) 0.0377(4) Uani 1 1 d . . .
H24 H 0.8466 0.1031 -0.1542 0.045 Uiso 1 1 calc R . .
C25 C 0.92857(12) 0.14805(11) -0.09484(6) 0.0369(4) Uani 1 1 d . . .
H25 H 0.9695 0.0926 -0.0949 0.044 Uiso 1 1 calc R . .
C26 C 0.94159(10) 0.22279(10) -0.05910(5) 0.0286(3) Uani 1 1 d . . .
H26 H 0.9907 0.2176 -0.0344 0.034 Uiso 1 1 calc R . .
C27 C 0.42674(9) 0.29762(9) 0.16301(5) 0.0211(2) Uani 1 1 d . . .
H27 H 0.4173 0.2353 0.1440 0.025 Uiso 1 1 calc R . .
H27A H 0.3644 0.3287 0.1668 0.025 Uiso 1 1 calc R . .
C28 C 0.46583(9) 0.27277(9) 0.21529(5) 0.0213(2) Uani 1 1 d . . .
C29 C 0.53036(9) 0.19624(10) 0.22267(5) 0.0239(3) Uani 1 1 d . . .
H29 H 0.5527 0.1608 0.1943 0.029 Uiso 1 1 calc R . .
C30 C 0.56241(10) 0.17128(11) 0.27112(5) 0.0300(3) Uani 1 1 d . . .
H30 H 0.6054 0.1183 0.2757 0.036 Uiso 1 1 calc R . .
C31 C 0.53144(10) 0.22382(12) 0.31253(5) 0.0343(3) Uani 1 1 d . . .
H31 H 0.5539 0.2076 0.3456 0.041 Uiso 1 1 calc R . .
C32 C 0.46768(11) 0.30004(12) 0.30567(5) 0.0349(3) Uani 1 1 d . . .
H32 H 0.4467 0.3361 0.3342 0.042 Uiso 1 1 calc R . .
C33 C 0.43384(10) 0.32458(10) 0.25725(5) 0.0277(3) Uani 1 1 d . . .
H33 H 0.3893 0.3763 0.2530 0.033 Uiso 1 1 calc R . .
C34 C 0.11198(8) 0.60732(9) 0.22387(4) 0.0182(2) Uani 1 1 d . . .
C35 C 0.18134(8) 0.62842(9) 0.26616(5) 0.0192(2) Uani 1 1 d . . .
N4 N 0.15623(7) 0.72177(7) 0.28424(4) 0.0200(2) Uani 1 1 d . . .
C36 C 0.07632(8) 0.76038(9) 0.26077(4) 0.0186(2) Uani 1 1 d . . .
C37 C 0.04965(8) 0.68744(9) 0.22047(4) 0.0178(2) Uani 1 1 d . . .
O7 O 0.24530(6) 0.57899(7) 0.28242(4) 0.0250(2) Uani 1 1 d . . .
O8 O 0.03920(6) 0.83705(6) 0.27264(3) 0.02262(19) Uani 1 1 d . . .
C38 C -0.02098(8) 0.68891(9) 0.18412(4) 0.0185(2) Uani 1 1 d . . .
C39 C -0.09602(8) 0.76345(9) 0.17207(5) 0.0194(2) Uani 1 1 d . . .
N5 N -0.14531(7) 0.72445(8) 0.13045(4) 0.0216(2) Uani 1 1 d . . .
C40 C -0.11022(9) 0.63442(9) 0.11387(5) 0.0202(2) Uani 1 1 d . . .
C41 C -0.03136(8) 0.60940(9) 0.15046(4) 0.0189(2) Uani 1 1 d . . .
O9 O -0.11425(7) 0.84023(7) 0.19258(4) 0.0256(2) Uani 1 1 d . . .
O10 O -0.13929(7) 0.58909(7) 0.07750(3) 0.0264(2) Uani 1 1 d . . .
C42 C 0.02763(8) 0.52835(9) 0.15501(4) 0.0188(2) Uani 1 1 d . . .
C43 C 0.03145(9) 0.43258(9) 0.12635(5) 0.0202(2) Uani 1 1 d . . .
N6 N 0.11049(7) 0.38414(7) 0.14493(4) 0.0202(2) Uani 1 1 d . . .
C44 C 0.15618(8) 0.43414(9) 0.18451(5) 0.0193(2) Uani 1 1 d . . .
C45 C 0.10078(8) 0.52788(9) 0.19131(4) 0.0186(2) Uani 1 1 d . . .
O11 O -0.02191(7) 0.40186(7) 0.09388(3) 0.0263(2) Uani 1 1 d . . .
O12 O 0.22591(6) 0.40634(7) 0.20633(4) 0.02461(19) Uani 1 1 d . . .
C46 C 0.20314(9) 0.77283(9) 0.32608(5) 0.0220(2) Uani 1 1 d . . .
H46 H 0.2514 0.7288 0.3413 0.026 Uiso 1 1 calc R . .
H46A H 0.1567 0.7881 0.3524 0.026 Uiso 1 1 calc R . .
C47 C 0.24926(8) 0.86777(9) 0.30918(5) 0.0195(2) Uani 1 1 d . . .
C48 C 0.30110(9) 0.87201(10) 0.26499(5) 0.0242(3) Uani 1 1 d . . .
H48 H 0.3039 0.8158 0.2436 0.029 Uiso 1 1 calc R . .
C49 C 0.34879(9) 0.95762(11) 0.25196(5) 0.0282(3) Uani 1 1 d . . .
H49 H 0.3837 0.9596 0.2217 0.034 Uiso 1 1 calc R . .
C50 C 0.34554(9) 1.04028(10) 0.28309(5) 0.0277(3) Uani 1 1 d . . .
H50 H 0.3791 1.0985 0.2746 0.033 Uiso 1 1 calc R . .
C51 C 0.29289(9) 1.03687(10) 0.32663(5) 0.0254(3) Uani 1 1 d . . .
H51 H 0.2901 1.0932 0.3480 0.030 Uiso 1 1 calc R . .
C52 C 0.24402(9) 0.95161(9) 0.33932(5) 0.0212(2) Uani 1 1 d . . .
H52 H 0.2068 0.9507 0.3688 0.025 Uiso 1 1 calc R . .
C53 C -0.22892(9) 0.77230(10) 0.10836(5) 0.0252(3) Uani 1 1 d . . .
H53 H -0.2708 0.7921 0.1361 0.030 Uiso 1 1 calc R . .
H53A H -0.2632 0.7236 0.0871 0.030 Uiso 1 1 calc R . .
C54 C -0.20809(9) 0.86207(10) 0.07663(5) 0.0242(3) Uani 1 1 d . . .
C55 C -0.21705(10) 0.95612(10) 0.09718(6) 0.0289(3) Uani 1 1 d . . .
H55 H -0.2341 0.9636 0.1316 0.035 Uiso 1 1 calc R . .
C56 C -0.20123(11) 1.03900(12) 0.06763(7) 0.0397(4) Uani 1 1 d . . .
H56 H -0.2084 1.1031 0.0817 0.048 Uiso 1 1 calc R . .
C57 C -0.17526(12) 1.02841(14) 0.01807(7) 0.0469(4) Uani 1 1 d . . .
H57 H -0.1636 1.0853 -0.0019 0.056 Uiso 1 1 calc R . .
C58 C -0.16600(12) 0.93512(15) -0.00280(7) 0.0470(4) Uani 1 1 d . . .
H58 H -0.1479 0.9282 -0.0370 0.056 Uiso 1 1 calc R . .
C59 C -0.18315(11) 0.85164(12) 0.02629(6) 0.0348(3) Uani 1 1 d . . .
H59 H -0.1778 0.7877 0.0118 0.042 Uiso 1 1 calc R . .
C60 C 0.14501(9) 0.29115(9) 0.12346(5) 0.0230(3) Uani 1 1 d . . .
H60 H 0.2145 0.2911 0.1253 0.028 Uiso 1 1 calc R . .
H60A H 0.1259 0.2878 0.0873 0.028 Uiso 1 1 calc R . .
C61 C 0.10905(9) 0.20048(9) 0.15015(5) 0.0201(2) Uani 1 1 d . . .
C62 C 0.02623(9) 0.15529(9) 0.13324(5) 0.0225(2) Uani 1 1 d . . .
H62 H -0.0077 0.1822 0.1052 0.027 Uiso 1 1 calc R . .
C63 C -0.00701(9) 0.07125(9) 0.15716(5) 0.0249(3) Uani 1 1 d . . .
H63 H -0.0636 0.0411 0.1455 0.030 Uiso 1 1 calc R . .
C64 C 0.04218(9) 0.03126(9) 0.19800(5) 0.0247(3) Uani 1 1 d . . .
H64 H 0.0194 -0.0263 0.2143 0.030 Uiso 1 1 calc R . .
C65 C 0.12469(10) 0.07549(10) 0.21508(5) 0.0251(3) Uani 1 1 d . . .
H65 H 0.1585 0.0481 0.2430 0.030 Uiso 1 1 calc R . .
C66 C 0.15801(9) 0.15990(10) 0.19138(5) 0.0234(3) Uani 1 1 d . . .
H66 H 0.2144 0.1901 0.2033 0.028 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C12 1.3836(17) . ?
C1 C4 1.4054(16) . ?
C1 C2 1.4993(16) . ?
C2 O1 1.2053(15) . ?
C2 N1 1.3921(16) . ?
N1 C3 1.3976(16) . ?
N1 C13 1.4747(15) . ?
C3 O2 1.2051(15) . ?
C3 C4 1.5073(16) . ?
C4 C5 1.3830(17) . ?
C5 C8 1.4050(16) . ?
C5 C6 1.5013(16) . ?
C6 O3 1.2030(15) . ?
C6 N2 1.3905(16) . ?
N2 C7 1.3902(15) . ?
N2 C20 1.4606(15) . ?
C7 O4 1.2040(15) . ?
C7 C8 1.5064(16) . ?
C8 C9 1.3847(16) . ?
C9 C12 1.4028(16) . ?
C9 C10 1.5065(16) . ?
C10 O5 1.2048(15) . ?
C10 N3 1.3896(15) . ?
N3 C11 1.4042(16) . ?
N3 C27 1.4728(15) . ?
C11 O6 1.2003(15) . ?
C11 C12 1.5051(16) . ?
C13 C14 1.5095(17) . ?
C13 H13 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.3880(19) . ?
C14 C19 1.3924(18) . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3889(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.5120(17) . ?
C20 H20 0.9900 . ?
C20 H20A 0.9900 . ?
C21 C26 1.3916(18) . ?
C21 C22 1.3932(19) . ?
C22 C23 1.3889(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.5178(17) . ?
C27 H27 0.9900 . ?
C27 H27A 0.9900 . ?
C28 C33 1.3953(18) . ?
C28 C29 1.3964(19) . ?
C29 C30 1.3929(18) . ?
C29 H29 0.9500 . ?
C30 C31 1.384(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.384(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.399(2) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C45 1.3847(17) . ?
C34 C37 1.4036(16) . ?
C34 C35 1.5053(17) . ?
C35 O7 1.2034(15) . ?
C35 N4 1.4000(16) . ?
N4 C36 1.3885(16) . ?
N4 C46 1.4559(15) . ?
C36 O8 1.2089(15) . ?
C36 C37 1.4961(16) . ?
C37 C38 1.3785(17) . ?
C38 C41 1.4024(17) . ?
C38 C39 1.4999(16) . ?
C39 O9 1.2027(15) . ?
C39 N5 1.3978(16) . ?
N5 C40 1.3912(16) . ?
N5 C53 1.4675(16) . ?
C40 O10 1.2072(15) . ?
C40 C41 1.5073(17) . ?
C41 C42 1.3860(17) . ?
C42 C45 1.4035(17) . ?
C42 C43 1.5030(17) . ?
C43 O11 1.2097(15) . ?
C43 N6 1.3851(16) . ?
N6 C44 1.3968(16) . ?
N6 C60 1.4692(15) . ?
C44 O12 1.1999(15) . ?
C44 C45 1.5069(16) . ?
C46 C47 1.5145(17) . ?
C46 H46 0.9900 . ?
C46 H46A 0.9900 . ?
C47 C52 1.3894(17) . ?
C47 C48 1.3937(18) . ?
C48 C49 1.3898(19) . ?
C48 H48 0.9500 . ?
C49 C50 1.390(2) . ?
C49 H49 0.9500 . ?
C50 C51 1.385(2) . ?
C50 H50 0.9500 . ?
C51 C52 1.3920(18) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C54 1.5089(18) . ?
C53 H53 0.9900 . ?
C53 H53A 0.9900 . ?
C54 C59 1.390(2) . ?
C54 C55 1.3910(19) . ?
C55 C56 1.388(2) . ?
C55 H55 0.9500 . ?
C56 C57 1.375(3) . ?
C56 H56 0.9500 . ?
C57 C58 1.385(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.391(2) . ?
C58 H58 0.9500 . ?
C59 H59 0.9500 . ?
C60 C61 1.5098(17) . ?
C60 H60 0.9900 . ?
C60 H60A 0.9900 . ?
C61 C62 1.3951(18) . ?
C61 C66 1.3956(18) . ?
C62 C63 1.3888(18) . ?
C62 H62 0.9500 . ?
C63 C64 1.3862(19) . ?
C63 H63 0.9500 . ?
C64 C65 1.3871(19) . ?
C64 H64 0.9500 . ?
C65 C66 1.3907(18) . ?
C65 H65 0.9500 . ?
C66 H66 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
C12 C1 C4 120.28(11) . . ?
C12 C1 C2 131.77(11) . . ?
C4 C1 C2 107.84(10) . . ?
O1 C2 N1 125.04(11) . . ?
O1 C2 C1 129.13(11) . . ?
N1 C2 C1 105.76(10) . . ?
C2 N1 C3 113.00(10) . . ?
C2 N1 C13 122.36(10) . . ?
C3 N1 C13 124.42(10) . . ?
O2 C3 N1 125.44(12) . . ?
O2 C3 C4 129.22(12) . . ?
N1 C3 C4 105.31(10) . . ?
C5 C4 C1 119.79(11) . . ?
C5 C4 C3 132.36(11) . . ?
C1 C4 C3 107.81(10) . . ?
C4 C5 C8 120.04(11) . . ?
C4 C5 C6 132.04(11) . . ?
C8 C5 C6 107.92(10) . . ?
O3 C6 N2 125.47(11) . . ?
O3 C6 C5 129.10(12) . . ?
N2 C6 C5 105.43(10) . . ?
C7 N2 C6 113.58(10) . . ?
C7 N2 C20 122.92(10) . . ?
C6 N2 C20 123.51(10) . . ?
O4 C7 N2 125.46(11) . . ?
O4 C7 C8 129.24(11) . . ?
N2 C7 C8 105.29(10) . . ?
C9 C8 C5 119.98(11) . . ?
C9 C8 C7 132.24(11) . . ?
C5 C8 C7 107.76(10) . . ?
C8 C9 C12 120.10(11) . . ?
C8 C9 C10 132.23(11) . . ?
C12 C9 C10 107.66(10) . . ?
O5 C10 N3 125.41(11) . . ?
O5 C10 C9 128.81(11) . . ?
N3 C10 C9 105.71(10) . . ?
C10 N3 C11 113.12(10) . . ?
C10 N3 C27 122.84(10) . . ?
C11 N3 C27 122.52(10) . . ?
O6 C11 N3 125.73(11) . . ?
O6 C11 C12 129.18(12) . . ?
N3 C11 C12 105.08(10) . . ?
C1 C12 C9 119.78(11) . . ?
C1 C12 C11 131.98(11) . . ?
C9 C12 C11 108.24(10) . . ?
N1 C13 C14 111.66(10) . . ?
N1 C13 H13 109.3 . . ?
C14 C13 H13 109.3 . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
H13 C13 H13A 107.9 . . ?
C15 C14 C19 119.40(12) . . ?
C15 C14 C13 120.18(12) . . ?
C19 C14 C13 120.41(12) . . ?
C14 C15 C16 120.24(13) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.00(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.30(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 119.78(13) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.29(13) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
N2 C20 C21 111.70(10) . . ?
N2 C20 H20 109.3 . . ?
C21 C20 H20 109.3 . . ?
N2 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
H20 C20 H20A 107.9 . . ?
C26 C21 C22 119.34(12) . . ?
C26 C21 C20 119.71(12) . . ?
C22 C21 C20 120.95(11) . . ?
C23 C22 C21 120.12(13) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.27(15) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.98(14) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.00(14) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 120.26(14) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
N3 C27 C28 115.13(10) . . ?
N3 C27 H27 108.5 . . ?
C28 C27 H27 108.5 . . ?
N3 C27 H27A 108.5 . . ?
C28 C27 H27A 108.5 . . ?
H27 C27 H27A 107.5 . . ?
C33 C28 C29 119.04(12) . . ?
C33 C28 C27 119.47(12) . . ?
C29 C28 C27 121.43(11) . . ?
C30 C29 C28 120.83(13) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C29 119.87(14) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 119.82(13) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 120.74(14) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C28 C33 C32 119.68(14) . . ?
C28 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C45 C34 C37 119.65(11) . . ?
C45 C34 C35 132.47(11) . . ?
C37 C34 C35 107.87(10) . . ?
O7 C35 N4 125.21(11) . . ?
O7 C35 C34 129.94(11) . . ?
N4 C35 C34 104.85(10) . . ?
C36 N4 C35 113.56(10) . . ?
C36 N4 C46 121.45(10) . . ?
C35 N4 C46 124.84(10) . . ?
O8 C36 N4 124.48(11) . . ?
O8 C36 C37 130.14(11) . . ?
N4 C36 C37 105.38(10) . . ?
C38 C37 C34 120.57(11) . . ?
C38 C37 C36 131.24(11) . . ?
C34 C37 C36 108.19(10) . . ?
C37 C38 C41 119.87(11) . . ?
C37 C38 C39 131.74(11) . . ?
C41 C38 C39 108.38(10) . . ?
O9 C39 N5 124.86(11) . . ?
O9 C39 C38 130.15(12) . . ?
N5 C39 C38 104.99(10) . . ?
C40 N5 C39 113.61(10) . . ?
C40 N5 C53 123.72(11) . . ?
C39 N5 C53 122.59(11) . . ?
O10 C40 N5 125.17(11) . . ?
O10 C40 C41 129.60(12) . . ?
N5 C40 C41 105.23(10) . . ?
C42 C41 C38 119.73(11) . . ?
C42 C41 C40 132.61(11) . . ?
C38 C41 C40 107.64(10) . . ?
C41 C42 C45 120.28(11) . . ?
C41 C42 C43 131.82(11) . . ?
C45 C42 C43 107.90(10) . . ?
O11 C43 N6 125.79(12) . . ?
O11 C43 C42 128.75(12) . . ?
N6 C43 C42 105.45(10) . . ?
C43 N6 C44 113.62(10) . . ?
C43 N6 C60 122.98(11) . . ?
C44 N6 C60 123.35(10) . . ?
O12 C44 N6 125.32(11) . . ?
O12 C44 C45 129.61(11) . . ?
N6 C44 C45 105.04(10) . . ?
C34 C45 C42 119.80(11) . . ?
C34 C45 C44 132.34(11) . . ?
C42 C45 C44 107.83(10) . . ?
N4 C46 C47 112.00(10) . . ?
N4 C46 H46 109.2 . . ?
C47 C46 H46 109.2 . . ?
N4 C46 H46A 109.2 . . ?
C47 C46 H46A 109.2 . . ?
H46 C46 H46A 107.9 . . ?
C52 C47 C48 118.76(12) . . ?
C52 C47 C46 119.76(11) . . ?
C48 C47 C46 121.40(11) . . ?
C49 C48 C47 120.69(12) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C48 C49 C50 120.22(12) . . ?
C48 C49 H49 119.9 . . ?
C50 C49 H49 119.9 . . ?
C51 C50 C49 119.25(12) . . ?
C51 C50 H50 120.4 . . ?
C49 C50 H50 120.4 . . ?
C50 C51 C52 120.54(12) . . ?
C50 C51 H51 119.7 . . ?
C52 C51 H51 119.7 . . ?
C47 C52 C51 120.48(12) . . ?
C47 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
N5 C53 C54 114.22(11) . . ?
N5 C53 H53 108.7 . . ?
C54 C53 H53 108.7 . . ?
N5 C53 H53A 108.7 . . ?
C54 C53 H53A 108.7 . . ?
H53 C53 H53A 107.6 . . ?
C59 C54 C55 119.55(13) . . ?
C59 C54 C53 120.39(13) . . ?
C55 C54 C53 120.02(12) . . ?
C56 C55 C54 120.25(14) . . ?
C56 C55 H55 119.9 . . ?
C54 C55 H55 119.9 . . ?
C57 C56 C55 120.05(16) . . ?
C57 C56 H56 120.0 . . ?
C55 C56 H56 120.0 . . ?
C56 C57 C58 120.22(15) . . ?
C56 C57 H57 119.9 . . ?
C58 C57 H57 119.9 . . ?
C57 C58 C59 120.14(16) . . ?
C57 C58 H58 119.9 . . ?
C59 C58 H58 119.9 . . ?
C54 C59 C58 119.77(16) . . ?
C54 C59 H59 120.1 . . ?
C58 C59 H59 120.1 . . ?
N6 C60 C61 113.43(10) . . ?
N6 C60 H60 108.9 . . ?
C61 C60 H60 108.9 . . ?
N6 C60 H60A 108.9 . . ?
C61 C60 H60A 108.9 . . ?
H60 C60 H60A 107.7 . . ?
C62 C61 C66 119.01(12) . . ?
C62 C61 C60 119.94(11) . . ?
C66 C61 C60 121.05(12) . . ?
C63 C62 C61 120.46(12) . . ?
C63 C62 H62 119.8 . . ?
C61 C62 H62 119.8 . . ?
C64 C63 C62 120.16(12) . . ?
C64 C63 H63 119.9 . . ?
C62 C63 H63 119.9 . . ?
C63 C64 C65 119.87(12) . . ?
C63 C64 H64 120.1 . . ?
C65 C64 H64 120.1 . . ?
C64 C65 C66 120.15(12) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C65 C66 C61 120.35(12) . . ?
C65 C66 H66 119.8 . . ?
C61 C66 H66 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 O1 -3.7(2) . . . . ?
C4 C1 C2 O1 172.43(12) . . . . ?
C12 C1 C2 N1 179.44(12) . . . . ?
C4 C1 C2 N1 -4.44(12) . . . . ?
O1 C2 N1 C3 -171.40(12) . . . . ?
C1 C2 N1 C3 5.64(13) . . . . ?
O1 C2 N1 C13 3.47(19) . . . . ?
C1 C2 N1 C13 -179.50(10) . . . . ?
C2 N1 C3 O2 173.46(12) . . . . ?
C13 N1 C3 O2 -1.3(2) . . . . ?
C2 N1 C3 C4 -4.53(13) . . . . ?
C13 N1 C3 C4 -179.27(10) . . . . ?
C12 C1 C4 C5 0.62(17) . . . . ?
C2 C1 C4 C5 -176.04(10) . . . . ?
C12 C1 C4 C3 178.46(10) . . . . ?
C2 C1 C4 C3 1.81(13) . . . . ?
O2 C3 C4 C5 1.0(2) . . . . ?
N1 C3 C4 C5 178.93(12) . . . . ?
O2 C3 C4 C1 -176.44(13) . . . . ?
N1 C3 C4 C1 1.46(13) . . . . ?
C1 C4 C5 C8 1.06(17) . . . . ?
C3 C4 C5 C8 -176.17(12) . . . . ?
C1 C4 C5 C6 -179.18(12) . . . . ?
C3 C4 C5 C6 3.6(2) . . . . ?
C4 C5 C6 O3 -1.0(2) . . . . ?
C8 C5 C6 O3 178.81(13) . . . . ?
C4 C5 C6 N2 179.54(12) . . . . ?
C8 C5 C6 N2 -0.68(13) . . . . ?
O3 C6 N2 C7 -178.37(12) . . . . ?
C5 C6 N2 C7 1.15(13) . . . . ?
O3 C6 N2 C20 1.74(19) . . . . ?
C5 C6 N2 C20 -178.74(10) . . . . ?
C6 N2 C7 O4 179.41(12) . . . . ?
C20 N2 C7 O4 -0.70(19) . . . . ?
C6 N2 C7 C8 -1.13(13) . . . . ?
C20 N2 C7 C8 178.76(10) . . . . ?
C4 C5 C8 C9 -1.41(17) . . . . ?
C6 C5 C8 C9 178.78(10) . . . . ?
C4 C5 C8 C7 179.84(10) . . . . ?
C6 C5 C8 C7 0.02(13) . . . . ?
O4 C7 C8 C9 1.5(2) . . . . ?
N2 C7 C8 C9 -177.90(12) . . . . ?
O4 C7 C8 C5 -179.93(12) . . . . ?
N2 C7 C8 C5 0.64(12) . . . . ?
C5 C8 C9 C12 0.09(17) . . . . ?
C7 C8 C9 C12 178.49(12) . . . . ?
C5 C8 C9 C10 178.74(11) . . . . ?
C7 C8 C9 C10 -2.9(2) . . . . ?
C8 C9 C10 O5 -5.7(2) . . . . ?
C12 C9 C10 O5 173.05(12) . . . . ?
C8 C9 C10 N3 177.21(12) . . . . ?
C12 C9 C10 N3 -4.02(12) . . . . ?
O5 C10 N3 C11 -172.50(11) . . . . ?
C9 C10 N3 C11 4.69(13) . . . . ?
O5 C10 N3 C27 -6.28(18) . . . . ?
C9 C10 N3 C27 170.92(10) . . . . ?
C10 N3 C11 O6 175.57(12) . . . . ?
C27 N3 C11 O6 9.30(19) . . . . ?
C10 N3 C11 C12 -3.48(13) . . . . ?
C27 N3 C11 C12 -169.76(10) . . . . ?
C4 C1 C12 C9 -1.93(17) . . . . ?
C2 C1 C12 C9 173.80(12) . . . . ?
C4 C1 C12 C11 178.86(12) . . . . ?
C2 C1 C12 C11 -5.4(2) . . . . ?
C8 C9 C12 C1 1.57(17) . . . . ?
C10 C9 C12 C1 -177.38(10) . . . . ?
C8 C9 C12 C11 -179.05(10) . . . . ?
C10 C9 C12 C11 2.00(13) . . . . ?
O6 C11 C12 C1 1.0(2) . . . . ?
N3 C11 C12 C1 179.99(12) . . . . ?
O6 C11 C12 C9 -178.30(13) . . . . ?
N3 C11 C12 C9 0.71(13) . . . . ?
C2 N1 C13 C14 64.62(15) . . . . ?
C3 N1 C13 C14 -121.11(13) . . . . ?
N1 C13 C14 C15 -104.28(14) . . . . ?
N1 C13 C14 C19 76.40(15) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
C13 C14 C15 C16 -179.20(12) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 C14 -0.35(19) . . . . ?
C15 C14 C19 C18 0.37(19) . . . . ?
C13 C14 C19 C18 179.69(11) . . . . ?
C7 N2 C20 C21 73.33(14) . . . . ?
C6 N2 C20 C21 -106.79(13) . . . . ?
N2 C20 C21 C26 -138.19(12) . . . . ?
N2 C20 C21 C22 41.61(16) . . . . ?
C26 C21 C22 C23 1.44(19) . . . . ?
C20 C21 C22 C23 -178.36(12) . . . . ?
C21 C22 C23 C24 -1.5(2) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C23 C24 C25 C26 1.1(2) . . . . ?
C22 C21 C26 C25 -0.12(19) . . . . ?
C20 C21 C26 C25 179.68(12) . . . . ?
C24 C25 C26 C21 -1.1(2) . . . . ?
C10 N3 C27 C28 77.37(14) . . . . ?
C11 N3 C27 C28 -117.68(12) . . . . ?
N3 C27 C28 C33 98.23(14) . . . . ?
N3 C27 C28 C29 -84.50(14) . . . . ?
C33 C28 C29 C30 0.24(19) . . . . ?
C27 C28 C29 C30 -177.04(11) . . . . ?
C28 C29 C30 C31 -1.1(2) . . . . ?
C29 C30 C31 C32 0.9(2) . . . . ?
C30 C31 C32 C33 0.2(2) . . . . ?
C29 C28 C33 C32 0.85(19) . . . . ?
C27 C28 C33 C32 178.18(12) . . . . ?
C31 C32 C33 C28 -1.1(2) . . . . ?
C45 C34 C35 O7 -0.6(2) . . . . ?
C37 C34 C35 O7 178.57(12) . . . . ?
C45 C34 C35 N4 179.42(12) . . . . ?
C37 C34 C35 N4 -1.38(13) . . . . ?
O7 C35 N4 C36 -176.45(12) . . . . ?
C34 C35 N4 C36 3.50(13) . . . . ?
O7 C35 N4 C46 -0.86(19) . . . . ?
C34 C35 N4 C46 179.09(11) . . . . ?
C35 N4 C36 O8 175.34(11) . . . . ?
C46 N4 C36 O8 -0.42(18) . . . . ?
C35 N4 C36 C37 -4.10(13) . . . . ?
C46 N4 C36 C37 -179.86(10) . . . . ?
C45 C34 C37 C38 -1.79(17) . . . . ?
C35 C34 C37 C38 178.90(10) . . . . ?
C45 C34 C37 C36 178.34(10) . . . . ?
C35 C34 C37 C36 -0.98(13) . . . . ?
O8 C36 C37 C38 3.7(2) . . . . ?
N4 C36 C37 C38 -176.86(12) . . . . ?
O8 C36 C37 C34 -176.39(12) . . . . ?
N4 C36 C37 C34 3.00(13) . . . . ?
C34 C37 C38 C41 0.56(17) . . . . ?
C36 C37 C38 C41 -179.59(11) . . . . ?
C34 C37 C38 C39 179.98(12) . . . . ?
C36 C37 C38 C39 -0.2(2) . . . . ?
C37 C38 C39 O9 -2.2(2) . . . . ?
C41 C38 C39 O9 177.28(13) . . . . ?
C37 C38 C39 N5 178.79(12) . . . . ?
C41 C38 C39 N5 -1.75(13) . . . . ?
O9 C39 N5 C40 -179.88(12) . . . . ?
C38 C39 N5 C40 -0.79(13) . . . . ?
O9 C39 N5 C53 -2.82(19) . . . . ?
C38 C39 N5 C53 176.28(11) . . . . ?
C39 N5 C40 O10 -177.05(12) . . . . ?
C53 N5 C40 O10 5.9(2) . . . . ?
C39 N5 C40 C41 2.80(13) . . . . ?
C53 N5 C40 C41 -174.23(11) . . . . ?
C37 C38 C41 C42 2.06(17) . . . . ?
C39 C38 C41 C42 -177.48(10) . . . . ?
C37 C38 C41 C40 -177.06(10) . . . . ?
C39 C38 C41 C40 3.40(13) . . . . ?
O10 C40 C41 C42 -2.9(2) . . . . ?
N5 C40 C41 C42 177.24(12) . . . . ?
O10 C40 C41 C38 176.04(13) . . . . ?
N5 C40 C41 C38 -3.79(13) . . . . ?
C38 C41 C42 C45 -3.46(17) . . . . ?
C40 C41 C42 C45 175.40(12) . . . . ?
C38 C41 C42 C43 177.64(12) . . . . ?
C40 C41 C42 C43 -3.5(2) . . . . ?
C41 C42 C43 O11 -5.2(2) . . . . ?
C45 C42 C43 O11 175.76(12) . . . . ?
C41 C42 C43 N6 174.92(12) . . . . ?
C45 C42 C43 N6 -4.08(13) . . . . ?
O11 C43 N6 C44 -176.35(12) . . . . ?
C42 C43 N6 C44 3.50(13) . . . . ?
O11 C43 N6 C60 6.15(19) . . . . ?
C42 C43 N6 C60 -174.00(10) . . . . ?
C43 N6 C44 O12 -179.89(11) . . . . ?
C60 N6 C44 O12 -2.40(19) . . . . ?
C43 N6 C44 C45 -1.59(13) . . . . ?
C60 N6 C44 C45 175.89(10) . . . . ?
C37 C34 C45 C42 0.39(17) . . . . ?
C35 C34 C45 C42 179.50(12) . . . . ?
C37 C34 C45 C44 178.05(12) . . . . ?
C35 C34 C45 C44 -2.8(2) . . . . ?
C41 C42 C45 C34 2.24(17) . . . . ?
C43 C42 C45 C34 -178.62(10) . . . . ?
C41 C42 C45 C44 -175.95(10) . . . . ?
C43 C42 C45 C44 3.19(13) . . . . ?
O12 C44 C45 C34 -0.8(2) . . . . ?
N6 C44 C45 C34 -179.02(12) . . . . ?
O12 C44 C45 C42 177.05(12) . . . . ?
N6 C44 C45 C42 -1.15(13) . . . . ?
C36 N4 C46 C47 -68.47(15) . . . . ?
C35 N4 C46 C47 116.27(13) . . . . ?
N4 C46 C47 C52 139.11(12) . . . . ?
N4 C46 C47 C48 -44.03(16) . . . . ?
C52 C47 C48 C49 1.71(19) . . . . ?
C46 C47 C48 C49 -175.17(12) . . . . ?
C47 C48 C49 C50 0.2(2) . . . . ?
C48 C49 C50 C51 -1.2(2) . . . . ?
C49 C50 C51 C52 0.3(2) . . . . ?
C48 C47 C52 C51 -2.63(18) . . . . ?
C46 C47 C52 C51 174.30(11) . . . . ?
C50 C51 C52 C47 1.66(19) . . . . ?
C40 N5 C53 C54 -107.48(14) . . . . ?
C39 N5 C53 C54 75.75(16) . . . . ?
N5 C53 C54 C59 83.33(16) . . . . ?
N5 C53 C54 C55 -98.98(15) . . . . ?
C59 C54 C55 C56 0.0(2) . . . . ?
C53 C54 C55 C56 -177.69(13) . . . . ?
C54 C55 C56 C57 -1.0(2) . . . . ?
C55 C56 C57 C58 0.9(2) . . . . ?
C56 C57 C58 C59 0.1(3) . . . . ?
C55 C54 C59 C58 1.0(2) . . . . ?
C53 C54 C59 C58 178.69(13) . . . . ?
C57 C58 C59 C54 -1.1(2) . . . . ?
C43 N6 C60 C61 -94.00(14) . . . . ?
C44 N6 C60 C61 88.74(14) . . . . ?
N6 C60 C61 C62 91.01(14) . . . . ?
N6 C60 C61 C66 -89.77(14) . . . . ?
C66 C61 C62 C63 0.09(18) . . . . ?
C60 C61 C62 C63 179.32(11) . . . . ?
C61 C62 C63 C64 -0.26(19) . . . . ?
C62 C63 C64 C65 0.15(19) . . . . ?
C63 C64 C65 C66 0.13(19) . . . . ?
C64 C65 C66 C61 -0.30(19) . . . . ?
C62 C61 C66 C65 0.19(18) . . . . ?
C60 C61 C66 C65 -179.04(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_H-Benzene
_database_code_depnum_ccdc_archive 'CCDC 1557861'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H21 N3 O6, C6 H6'
_chemical_formula_sum            'C39 H27 N3 O6'
_chemical_formula_weight         633.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.1609(11)
_cell_length_b                   11.1609(11)
_cell_length_c                   42.683(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4604.5(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3606
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      30.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1980
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17576
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.49
_reflns_number_total             1914
_reflns_number_gt                1887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0229P)²+8.4884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1914
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_restrained_S_all      1.356
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4132(2) 0.6022(2) 0.36447(5) 0.0201(5) Uani 1 1 d . . .
C2 C 0.2678(2) 0.5226(2) 0.36453(5) 0.0195(4) Uani 1 1 d . . .
C3 C 0.2286(2) 0.3734(2) 0.36799(5) 0.0213(5) Uani 1 1 d . . .
N1 N 0.35313(18) 0.37403(18) 0.37087(4) 0.0225(4) Uani 1 1 d . . .
C4 C 0.4689(2) 0.5055(2) 0.36798(5) 0.0230(5) Uani 1 1 d . . .
O1 O 0.11540(15) 0.27049(15) 0.36825(4) 0.0275(4) Uani 1 1 d . . .
O2 O 0.58762(16) 0.53129(16) 0.36848(4) 0.0317(4) Uani 1 1 d . . .
C5 C 0.3620(2) 0.2490(2) 0.37736(5) 0.0269(5) Uani 1 1 d . . .
H5 H 0.4504 0.2616 0.3691 0.032 Uiso 1 1 calc R . .
H5A H 0.2855 0.1688 0.3665 0.032 Uiso 1 1 calc R . .
C6 C 0.3534(2) 0.2198(2) 0.41214(5) 0.0261(5) Uani 1 1 d . . .
C7 C 0.2373(2) 0.1062(2) 0.42475(6) 0.0314(6) Uani 1 1 d . . .
H7 H 0.1629 0.0468 0.4114 0.038 Uiso 1 1 calc R . .
C8 C 0.2292(3) 0.0788(3) 0.45652(6) 0.0392(6) Uani 1 1 d . . .
H8 H 0.1498 0.0003 0.4648 0.047 Uiso 1 1 calc R . .
C9 C 0.3363(3) 0.1655(3) 0.47625(6) 0.0398(6) Uani 1 1 d . . .
H9 H 0.3305 0.1467 0.4981 0.048 Uiso 1 1 calc R . .
C10 C 0.4519(3) 0.2800(3) 0.46401(6) 0.0400(6) Uani 1 1 d . . .
H10 H 0.5252 0.3403 0.4775 0.048 Uiso 1 1 calc R . .
C11 C 0.4606(3) 0.3062(3) 0.43220(6) 0.0328(6) Uani 1 1 d . . .
H11 H 0.5406 0.3842 0.4239 0.039 Uiso 1 1 calc R . .
C12 C 0.1974(3) 0.5598(3) 0.44718(6) 0.0529(8) Uani 1 1 d . . .
H12 H 0.1040 0.4865 0.4471 0.063 Uiso 1 1 calc R . .
C13 C 0.2266(3) 0.6958(3) 0.44722(6) 0.0511(8) Uani 1 1 d . . .
H13 H 0.1532 0.7159 0.4473 0.061 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(3) 2_665 ?
C1 C2 1.407(3) . ?
C1 C4 1.498(3) . ?
C2 C1 1.384(3) 3_565 ?
C2 C3 1.502(3) . ?
C3 O1 1.210(3) . ?
C3 N1 1.392(3) . ?
N1 C4 1.393(3) . ?
N1 C5 1.474(3) . ?
C4 O2 1.208(3) . ?
C5 C6 1.512(3) . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C7 1.390(3) . ?
C6 C11 1.393(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.383(4) 2_665 ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C12 1.383(4) 3_565 ?
C13 H13 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 C1 C2 119.8(2) 2_665 . ?
C2 C1 C4 131.95(19) 2_665 . ?
C2 C1 C4 107.91(18) . . ?
C1 C2 C1 120.2(2) 3_565 . ?
C1 C2 C3 131.67(19) 3_565 . ?
C1 C2 C3 107.78(18) . . ?
O1 C3 N1 124.72(19) . . ?
O1 C3 C2 129.9(2) . . ?
N1 C3 C2 105.43(17) . . ?
C3 N1 C4 113.27(17) . . ?
C3 N1 C5 123.46(18) . . ?
C4 N1 C5 123.24(18) . . ?
O2 C4 N1 125.35(19) . . ?
O2 C4 C1 129.1(2) . . ?
N1 C4 C1 105.52(17) . . ?
N1 C5 C6 111.18(17) . . ?
N1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
H5 C5 H5A 108.0 . . ?
C7 C6 C11 118.7(2) . . ?
C7 C6 C5 120.4(2) . . ?
C11 C6 C5 120.9(2) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C13 C12 C13 120.0(3) 2_665 . ?
C13 C12 H12 120.0 2_665 . ?
C13 C12 H12 120.0 . . ?
C12 C13 C12 120.0(3) 3_565 . ?
C12 C13 H13 120.0 3_565 . ?
C12 C13 H13 120.0 . . ?

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
C2 C1 C2 C1 0.4(4) 2_665 . . 3_565 ?
C4 C1 C2 C1 174.12(15) . . . 3_565 ?
C2 C1 C2 C3 -173.93(14) 2_665 . . . ?
C4 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 O1 8.9(4) 3_565 . . . ?
C1 C2 C3 O1 -177.7(2) . . . . ?
C1 C2 C3 N1 -171.4(2) 3_565 . . . ?
C1 C2 C3 N1 2.0(2) . . . . ?
O1 C3 N1 C4 176.4(2) . . . . ?
C2 C3 N1 C4 -3.3(2) . . . . ?
O1 C3 N1 C5 -5.5(3) . . . . ?
C2 C3 N1 C5 174.81(17) . . . . ?
C3 N1 C4 O2 -177.1(2) . . . . ?
C5 N1 C4 O2 4.8(3) . . . . ?
C3 N1 C4 C1 3.2(2) . . . . ?
C5 N1 C4 C1 -174.91(17) . . . . ?
C2 C1 C4 O2 -8.7(4) 2_665 . . . ?
C2 C1 C4 O2 178.6(2) . . . . ?
C2 C1 C4 N1 171.0(2) 2_665 . . . ?
C2 C1 C4 N1 -1.7(2) . . . . ?
C3 N1 C5 C6 -84.9(2) . . . . ?
C4 N1 C5 C6 93.0(2) . . . . ?
N1 C5 C6 C7 110.4(2) . . . . ?
N1 C5 C6 C11 -69.1(3) . . . . ?
C11 C6 C7 C8 -0.6(3) . . . . ?
C5 C6 C7 C8 179.8(2) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C6 0.8(4) . . . . ?
C7 C6 C11 C10 -0.1(3) . . . . ?
C5 C6 C11 C10 179.4(2) . . . . ?
C13 C12 C13 C12 0.2(6) 2_665 . . 3_565 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_F-chlorobenzene
_database_code_depnum_ccdc_archive 'CCDC 1557870'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H18 F3 N3 O6, C6 H5 Cl'
_chemical_formula_sum            'C39 H23 Cl F3 N3 O6'
_chemical_formula_weight         722.05

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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.3405(13)
_cell_length_b                   11.3405(13)
_cell_length_c                   43.872(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4886.3(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3417
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      30.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2220
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17005
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2023
_reflns_number_gt                1491
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1576P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2023
_refine_ls_number_parameters     187
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2524
_refine_ls_wR_factor_gt          0.2126
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6047(3) 0.1919(3) 0.03173(7) 0.0293(8) Uani 1 1 d . . .
C2 C 0.7467(3) 0.2721(3) 0.03168(7) 0.0284(8) Uani 1 1 d . . .
C3 C 0.8047(4) 0.1785(3) 0.03429(8) 0.0347(8) Uani 1 1 d . . .
N1 N 0.6917(3) 0.0482(3) 0.03643(6) 0.0362(8) Uani 1 1 d . . .
C4 C 0.5685(4) 0.0451(3) 0.03413(7) 0.0330(8) Uani 1 1 d . . .
O1 O 0.9213(3) 0.2058(3) 0.03469(6) 0.0492(8) Uani 1 1 d . . .
O2 O 0.4581(3) -0.0569(2) 0.03401(6) 0.0429(7) Uani 1 1 d . . .
C5 C 0.7019(4) -0.0744(4) 0.04179(8) 0.0430(10) Uani 1 1 d . . .
H5 H 0.7906 -0.0589 0.0341 0.052 Uiso 1 1 calc R . .
H5A H 0.6290 -0.1517 0.0303 0.052 Uiso 1 1 calc R . .
C6 C 0.6893(4) -0.1105(4) 0.07511(8) 0.0411(9) Uani 1 1 d . . .
C7 C 0.7932(4) -0.0331(4) 0.09569(10) 0.0547(11) Uani 1 1 d . . .
H7 H 0.8748 0.0429 0.0884 0.066 Uiso 1 1 calc R . .
C8 C 0.7808(6) -0.0641(5) 0.12646(10) 0.0667(13) Uani 1 1 d . . .
H8 H 0.8519 -0.0098 0.1403 0.080 Uiso 1 1 calc R . .
C9 C 0.6642(6) -0.1740(5) 0.13634(10) 0.0660(13) Uani 1 1 d . . .
C10 C 0.5593(6) -0.2538(5) 0.11720(11) 0.0688(14) Uani 1 1 d . . .
H10 H 0.4789 -0.3302 0.1248 0.083 Uiso 1 1 calc R . .
C11 C 0.5724(5) -0.2212(4) 0.08649(9) 0.0543(11) Uani 1 1 d . . .
H11 H 0.4999 -0.2759 0.0730 0.065 Uiso 1 1 calc R . .
F1 F 0.6507(4) -0.2069(4) 0.16643(6) 0.1013(12) Uani 1 1 d . . .
Cl1 Cl 0.8684(5) 0.3008(6) 0.10828(12) 0.1008(16) Uani 0.33 1 d P A -1
C12 C 0.7339(12) 0.3261(16) 0.1113(2) 0.073(2) Uani 0.33 1 d PGU A -1
C13 C 0.7602(10) 0.4596(14) 0.1123(3) 0.074(2) Uani 0.33 1 d PGU A -1
H13 H 0.8515 0.5329 0.1125 0.088 Uiso 0.33 1 calc PR A -1
C14 C 0.6529(14) 0.4859(13) 0.1130(3) 0.074(2) Uani 0.33 1 d PGU A -1
H14 H 0.6709 0.5771 0.1136 0.089 Uiso 0.33 1 calc PR A -1
C15 C 0.5193(12) 0.3786(16) 0.1127(3) 0.074(2) Uani 0.33 1 d PGU A -1
H15 H 0.4460 0.3965 0.1132 0.089 Uiso 0.33 1 calc PR A -1
C16 C 0.4930(10) 0.2451(14) 0.1117(3) 0.074(2) Uani 0.33 1 d PGU A -1
H16 H 0.4017 0.1717 0.1115 0.089 Uiso 0.33 1 calc PR A -1
C17 C 0.6003(13) 0.2188(13) 0.1110(3) 0.074(2) Uani 0.33 1 d PGU A -1
H17 H 0.5823 0.1276 0.1104 0.088 Uiso 0.33 1 calc PR A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(5) 3_665 ?
C1 C2 1.398(4) . ?
C1 C4 1.507(4) . ?
C2 C1 1.384(5) 2_655 ?
C2 C3 1.508(4) . ?
C3 O1 1.198(4) . ?
C3 N1 1.393(5) . ?
N1 C4 1.384(4) . ?
N1 C5 1.471(4) . ?
C4 O2 1.206(4) . ?
C5 C6 1.505(5) . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C11 1.385(5) . ?
C6 C7 1.393(5) . ?
C7 C8 1.384(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.357(7) . ?
C8 H8 0.9500 . ?
C9 F1 1.360(5) . ?
C9 C10 1.365(7) . ?
C10 C11 1.385(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
Cl1 C12 1.693(7) . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 H17 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 C1 C2 119.9(3) 3_665 . ?
C2 C1 C4 132.0(3) 3_665 . ?
C2 C1 C4 107.9(3) . . ?
C1 C2 C1 120.1(3) 2_655 . ?
C1 C2 C3 131.7(3) 2_655 . ?
C1 C2 C3 107.9(3) . . ?
O1 C3 N1 125.8(3) . . ?
O1 C3 C2 129.3(3) . . ?
N1 C3 C2 105.0(3) . . ?
C4 N1 C3 113.8(3) . . ?
C4 N1 C5 122.9(3) . . ?
C3 N1 C5 123.3(3) . . ?
O2 C4 N1 125.1(3) . . ?
O2 C4 C1 129.6(3) . . ?
N1 C4 C1 105.3(3) . . ?
N1 C5 C6 111.7(3) . . ?
N1 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
N1 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
H5 C5 H5A 107.9 . . ?
C11 C6 C7 117.5(4) . . ?
C11 C6 C5 120.9(4) . . ?
C7 C6 C5 121.5(4) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C7 118.3(4) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 F1 119.1(5) . . ?
C8 C9 C10 122.6(4) . . ?
F1 C9 C10 118.3(5) . . ?
C9 C10 C11 118.6(5) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C6 C11 C10 121.2(4) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C17 120.0 . . ?
C13 C12 Cl1 117.8(8) . . ?
C17 C12 Cl1 122.1(8) . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.0 . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?

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
C2 C1 C2 C1 0.3(6) 3_665 . . 2_655 ?
C4 C1 C2 C1 -175.7(2) . . . 2_655 ?
C2 C1 C2 C3 175.6(2) 3_665 . . . ?
C4 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 O1 -6.5(6) 2_655 . . . ?
C1 C2 C3 O1 179.1(3) . . . . ?
C1 C2 C3 N1 173.1(3) 2_655 . . . ?
C1 C2 C3 N1 -1.3(3) . . . . ?
O1 C3 N1 C4 -177.5(3) . . . . ?
C2 C3 N1 C4 2.8(4) . . . . ?
O1 C3 N1 C5 4.6(5) . . . . ?
C2 C3 N1 C5 -175.0(3) . . . . ?
C3 N1 C4 O2 176.6(3) . . . . ?
C5 N1 C4 O2 -5.6(5) . . . . ?
C3 N1 C4 C1 -3.1(4) . . . . ?
C5 N1 C4 C1 174.8(3) . . . . ?
C2 C1 C4 O2 7.1(6) 3_665 . . . ?
C2 C1 C4 O2 -177.6(3) . . . . ?
C2 C1 C4 N1 -173.3(3) 3_665 . . . ?
C2 C1 C4 N1 2.1(3) . . . . ?
C4 N1 C5 C6 -83.0(4) . . . . ?
C3 N1 C5 C6 94.6(4) . . . . ?
N1 C5 C6 C11 107.0(4) . . . . ?
N1 C5 C6 C7 -72.0(4) . . . . ?
C11 C6 C7 C8 -0.5(6) . . . . ?
C5 C6 C7 C8 178.5(4) . . . . ?
C6 C7 C8 C9 0.8(7) . . . . ?
C7 C8 C9 F1 179.3(4) . . . . ?
C7 C8 C9 C10 -0.5(7) . . . . ?
C8 C9 C10 C11 0.0(7) . . . . ?
F1 C9 C10 C11 -179.8(4) . . . . ?
C7 C6 C11 C10 0.0(6) . . . . ?
C5 C6 C11 C10 -179.0(4) . . . . ?
C9 C10 C11 C6 0.3(7) . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
Cl1 C12 C13 C14 176.3(8) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C12 0.0 . . . . ?
C13 C12 C17 C16 0.0 . . . . ?
Cl1 C12 C17 C16 -176.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_H-yellow
_database_code_depnum_ccdc_archive 'CCDC 1557859'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H21 N3 O6'
_chemical_formula_sum            'C33 H21 N3 O6'
_chemical_formula_weight         555.53

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 0.0000 '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'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.6136(16)
_cell_length_b                   13.690(3)
_cell_length_c                   24.789(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2583.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93
_cell_measurement_reflns_used    8092
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      30.9

_exptl_crystal_description       Platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42968
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3344
_reflns_number_gt                3091
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0953P)²+0.3881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         3344
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_restrained_S_all      1.213
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3734(4) -0.05433(19) 0.71489(11) 0.0270(5) Uani 1 1 d . . .
C2 C 0.3962(4) -0.1363(2) 0.67519(11) 0.0290(6) Uani 1 1 d . . .
N1 N 0.3284(4) -0.10116(18) 0.62683(9) 0.0324(5) Uani 1 1 d . . .
C3 C 0.2650(4) -0.0052(2) 0.63048(11) 0.0309(6) Uani 1 1 d . . .
C4 C 0.2953(4) 0.02487(19) 0.68806(11) 0.0270(5) Uani 1 1 d . . .
O1 O 0.4545(3) -0.21716(14) 0.68210(9) 0.0371(5) Uani 1 1 d . . .
O2 O 0.1959(3) 0.03859(17) 0.59383(8) 0.0388(5) Uani 1 1 d . . .
C5 C 0.2461(3) 0.10665(19) 0.71700(11) 0.0261(5) Uani 1 1 d . . .
C6 C 0.1522(4) 0.1991(2) 0.70036(11) 0.0288(6) Uani 1 1 d . . .
N2 N 0.1166(3) 0.24773(16) 0.74862(10) 0.0299(5) Uani 1 1 d . . .
C7 C 0.1785(4) 0.19916(19) 0.79442(12) 0.0284(6) Uani 1 1 d . . .
C8 C 0.2700(4) 0.10988(19) 0.77320(11) 0.0259(5) Uani 1 1 d . . .
O3 O 0.1110(3) 0.22724(16) 0.65626(8) 0.0366(5) Uani 1 1 d . . .
O4 O 0.1520(3) 0.22442(15) 0.84016(8) 0.0337(5) Uani 1 1 d . . .
C9 C 0.3507(3) 0.03273(19) 0.79912(10) 0.0245(5) Uani 1 1 d . . .
C10 C 0.3978(4) 0.0151(2) 0.85743(11) 0.0280(5) Uani 1 1 d . . .
N3 N 0.4690(3) -0.07842(17) 0.85904(9) 0.0297(5) Uani 1 1 d . . .
C11 C 0.4737(4) -0.1239(2) 0.80881(11) 0.0276(5) Uani 1 1 d . . .
C12 C 0.4018(3) -0.05042(18) 0.76993(11) 0.0251(5) Uani 1 1 d . . .
O5 O 0.3814(3) 0.06922(15) 0.89563(8) 0.0348(5) Uani 1 1 d . . .
O6 O 0.5244(3) -0.20623(14) 0.80071(9) 0.0329(5) Uani 1 1 d . . .
C13 C 0.3143(5) -0.1614(3) 0.57812(12) 0.0410(7) Uani 1 1 d . . .
H13 H 0.2005 -0.1480 0.5603 0.049 Uiso 1 1 calc R . .
H13A H 0.3160 -0.2312 0.5885 0.049 Uiso 1 1 calc R . .
C14 C 0.4616(4) -0.1420(2) 0.53864(11) 0.0319(6) Uani 1 1 d . . .
C15 C 0.6326(5) -0.1647(2) 0.55274(14) 0.0402(7) Uani 1 1 d . . .
H15 H 0.6576 -0.1935 0.5867 0.048 Uiso 1 1 calc R . .
C16 C 0.7679(5) -0.1448(3) 0.5164(2) 0.0588(11) Uani 1 1 d . . .
H16 H 0.8863 -0.1589 0.5256 0.071 Uiso 1 1 calc R . .
C17 C 0.7272(7) -0.1039(3) 0.46602(18) 0.0646(14) Uani 1 1 d . . .
H17 H 0.8190 -0.0890 0.4414 0.077 Uiso 1 1 calc R . .
C18 C 0.5573(8) -0.0853(3) 0.45210(15) 0.0623(13) Uani 1 1 d . . .
H18 H 0.5303 -0.0601 0.4174 0.075 Uiso 1 1 calc R . .
C19 C 0.4248(6) -0.1031(3) 0.48865(13) 0.0462(8) Uani 1 1 d . . .
H19 H 0.3067 -0.0885 0.4793 0.055 Uiso 1 1 calc R . .
C20 C 0.0008(4) 0.3323(2) 0.75178(15) 0.0338(6) Uani 1 1 d . . .
H20 H -0.0715 0.3267 0.7848 0.041 Uiso 1 1 calc R . .
H20A H -0.0799 0.3310 0.7205 0.041 Uiso 1 1 calc R . .
C21 C 0.0948(4) 0.42994(19) 0.75262(12) 0.0280(5) Uani 1 1 d . . .
C22 C 0.1233(4) 0.4802(2) 0.70493(11) 0.0304(6) Uani 1 1 d . . .
H22 H 0.0865 0.4526 0.6716 0.036 Uiso 1 1 calc R . .
C23 C 0.2059(4) 0.5714(2) 0.70548(12) 0.0319(6) Uani 1 1 d . . .
H23 H 0.2257 0.6055 0.6726 0.038 Uiso 1 1 calc R . .
C24 C 0.2589(4) 0.6120(2) 0.75412(13) 0.0322(6) Uani 1 1 d . . .
H24 H 0.3156 0.6739 0.7545 0.039 Uiso 1 1 calc R . .
C25 C 0.2296(4) 0.5628(2) 0.80217(12) 0.0341(6) Uani 1 1 d . . .
H25 H 0.2643 0.5911 0.8355 0.041 Uiso 1 1 calc R . .
C26 C 0.1485(4) 0.4713(2) 0.80113(12) 0.0317(6) Uani 1 1 d . . .
H26 H 0.1298 0.4369 0.8339 0.038 Uiso 1 1 calc R . .
C27 C 0.5280(4) -0.1278(2) 0.90810(12) 0.0351(6) Uani 1 1 d . . .
H27 H 0.5321 -0.0801 0.9380 0.042 Uiso 1 1 calc R . .
H27A H 0.6485 -0.1530 0.9024 0.042 Uiso 1 1 calc R . .
C28 C 0.4090(4) -0.2116(2) 0.92374(11) 0.0332(6) Uani 1 1 d . . .
C29 C 0.4775(5) -0.3050(2) 0.93021(13) 0.0392(7) Uani 1 1 d . . .
H29 H 0.5993 -0.3161 0.9245 0.047 Uiso 1 1 calc R . .
C30 C 0.3693(6) -0.3824(3) 0.94498(13) 0.0456(8) Uani 1 1 d . . .
H30 H 0.4175 -0.4457 0.9502 0.055 Uiso 1 1 calc R . .
C31 C 0.1900(5) -0.3667(3) 0.95210(13) 0.0461(9) Uani 1 1 d . . .
H31 H 0.1151 -0.4196 0.9615 0.055 Uiso 1 1 calc R . .
C32 C 0.1215(5) -0.2741(3) 0.94541(13) 0.0461(8) Uani 1 1 d . . .
H32 H -0.0009 -0.2634 0.9501 0.055 Uiso 1 1 calc R . .
C33 C 0.2300(4) -0.1965(3) 0.93190(13) 0.0396(7) Uani 1 1 d . . .
H33 H 0.1821 -0.1327 0.9282 0.048 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C12 1.382(4) . ?
C1 C4 1.404(4) . ?
C1 C2 1.503(4) . ?
C2 O1 1.204(4) . ?
C2 N1 1.391(4) . ?
N1 C3 1.403(4) . ?
N1 C13 1.466(4) . ?
C3 O2 1.208(4) . ?
C3 C4 1.503(4) . ?
C4 C5 1.382(4) . ?
C5 C8 1.405(4) . ?
C5 C6 1.512(4) . ?
C6 O3 1.201(3) . ?
C6 N2 1.395(4) . ?
N2 C7 1.398(4) . ?
N2 C20 1.457(3) . ?
C7 O4 1.202(3) . ?
C7 C8 1.502(4) . ?
C8 C9 1.381(4) . ?
C9 C12 1.404(4) . ?
C9 C10 1.509(4) . ?
C10 O5 1.209(3) . ?
C10 N3 1.391(4) . ?
N3 C11 1.393(4) . ?
N3 C27 1.462(4) . ?
C11 O6 1.207(3) . ?
C11 C12 1.497(4) . ?
C13 C14 1.512(4) . ?
C13 H13 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C19 1.377(4) . ?
C14 C15 1.383(5) . ?
C15 C16 1.396(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.363(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.516(4) . ?
C20 H20 0.9900 . ?
C20 H20A 0.9900 . ?
C21 C22 1.385(4) . ?
C21 C26 1.391(4) . ?
C22 C23 1.398(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.512(4) . ?
C27 H27 0.9900 . ?
C27 H27A 0.9900 . ?
C28 C29 1.391(4) . ?
C28 C33 1.394(5) . ?
C29 C30 1.391(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.393(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.387(5) . ?
C32 H32 0.9500 . ?
C33 H33 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
C12 C1 C4 120.2(3) . . ?
C12 C1 C2 131.1(3) . . ?
C4 C1 C2 108.4(2) . . ?
O1 C2 N1 125.3(3) . . ?
O1 C2 C1 129.5(3) . . ?
N1 C2 C1 105.2(2) . . ?
C2 N1 C3 113.4(2) . . ?
C2 N1 C13 122.8(3) . . ?
C3 N1 C13 123.7(3) . . ?
O2 C3 N1 124.4(3) . . ?
O2 C3 C4 130.2(3) . . ?
N1 C3 C4 105.3(2) . . ?
C5 C4 C1 119.6(3) . . ?
C5 C4 C3 132.3(3) . . ?
C1 C4 C3 107.7(2) . . ?
C4 C5 C8 120.4(3) . . ?
C4 C5 C6 131.7(3) . . ?
C8 C5 C6 107.8(2) . . ?
O3 C6 N2 125.2(3) . . ?
O3 C6 C5 129.8(3) . . ?
N2 C6 C5 104.9(2) . . ?
C6 N2 C7 113.8(2) . . ?
C6 N2 C20 122.8(2) . . ?
C7 N2 C20 122.6(3) . . ?
O4 C7 N2 124.9(3) . . ?
O4 C7 C8 130.0(3) . . ?
N2 C7 C8 105.0(2) . . ?
C9 C8 C5 119.6(2) . . ?
C9 C8 C7 131.8(2) . . ?
C5 C8 C7 108.2(2) . . ?
C8 C9 C12 120.2(2) . . ?
C8 C9 C10 132.4(2) . . ?
C12 C9 C10 107.4(2) . . ?
O5 C10 N3 125.6(3) . . ?
O5 C10 C9 128.9(3) . . ?
N3 C10 C9 105.5(2) . . ?
C10 N3 C11 113.3(2) . . ?
C10 N3 C27 124.7(2) . . ?
C11 N3 C27 121.9(2) . . ?
O6 C11 N3 125.1(3) . . ?
O6 C11 C12 129.6(3) . . ?
N3 C11 C12 105.4(2) . . ?
C1 C12 C9 119.8(3) . . ?
C1 C12 C11 131.8(3) . . ?
C9 C12 C11 108.3(2) . . ?
N1 C13 C14 112.3(3) . . ?
N1 C13 H13 109.1 . . ?
C14 C13 H13 109.1 . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
H13 C13 H13A 107.9 . . ?
C19 C14 C15 120.4(3) . . ?
C19 C14 C13 119.9(3) . . ?
C15 C14 C13 119.7(3) . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 119.4(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.7(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 120.8(4) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
N2 C20 C21 114.6(2) . . ?
N2 C20 H20 108.6 . . ?
C21 C20 H20 108.6 . . ?
N2 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
H20 C20 H20A 107.6 . . ?
C22 C21 C26 119.3(3) . . ?
C22 C21 C20 120.0(3) . . ?
C26 C21 C20 120.6(3) . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.4(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C21 C26 C25 120.7(3) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
N3 C27 C28 112.4(2) . . ?
N3 C27 H27 109.1 . . ?
C28 C27 H27 109.1 . . ?
N3 C27 H27A 109.1 . . ?
C28 C27 H27A 109.1 . . ?
H27 C27 H27A 107.9 . . ?
C29 C28 C33 119.1(3) . . ?
C29 C28 C27 120.2(3) . . ?
C33 C28 C27 120.7(3) . . ?
C28 C29 C30 120.6(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C31 119.8(4) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C32 C31 C30 119.7(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 120.5(3) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C32 C33 C28 120.2(3) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?

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
C12 C1 C2 O1 -4.6(5) . . . . ?
C4 C1 C2 O1 -178.4(3) . . . . ?
C12 C1 C2 N1 173.3(3) . . . . ?
C4 C1 C2 N1 -0.5(3) . . . . ?
O1 C2 N1 C3 178.4(3) . . . . ?
C1 C2 N1 C3 0.4(3) . . . . ?
O1 C2 N1 C13 2.3(5) . . . . ?
C1 C2 N1 C13 -175.7(3) . . . . ?
C2 N1 C3 O2 -177.7(3) . . . . ?
C13 N1 C3 O2 -1.6(5) . . . . ?
C2 N1 C3 C4 -0.1(3) . . . . ?
C13 N1 C3 C4 175.9(3) . . . . ?
C12 C1 C4 C5 -0.3(4) . . . . ?
C2 C1 C4 C5 174.3(2) . . . . ?
C12 C1 C4 C3 -174.1(2) . . . . ?
C2 C1 C4 C3 0.4(3) . . . . ?
O2 C3 C4 C5 4.4(5) . . . . ?
N1 C3 C4 C5 -173.0(3) . . . . ?
O2 C3 C4 C1 177.2(3) . . . . ?
N1 C3 C4 C1 -0.2(3) . . . . ?
C1 C4 C5 C8 -1.6(4) . . . . ?
C3 C4 C5 C8 170.5(3) . . . . ?
C1 C4 C5 C6 -176.2(3) . . . . ?
C3 C4 C5 C6 -4.1(5) . . . . ?
C4 C5 C6 O3 -7.4(5) . . . . ?
C8 C5 C6 O3 177.5(3) . . . . ?
C4 C5 C6 N2 171.3(3) . . . . ?
C8 C5 C6 N2 -3.8(3) . . . . ?
O3 C6 N2 C7 179.8(3) . . . . ?
C5 C6 N2 C7 1.1(3) . . . . ?
O3 C6 N2 C20 9.6(4) . . . . ?
C5 C6 N2 C20 -169.2(2) . . . . ?
C6 N2 C7 O4 -174.7(3) . . . . ?
C20 N2 C7 O4 -4.4(4) . . . . ?
C6 N2 C7 C8 1.9(3) . . . . ?
C20 N2 C7 C8 172.2(2) . . . . ?
C4 C5 C8 C9 3.1(4) . . . . ?
C6 C5 C8 C9 178.9(2) . . . . ?
C4 C5 C8 C7 -170.8(2) . . . . ?
C6 C5 C8 C7 5.0(3) . . . . ?
O4 C7 C8 C9 -0.9(5) . . . . ?
N2 C7 C8 C9 -177.2(3) . . . . ?
O4 C7 C8 C5 172.0(3) . . . . ?
N2 C7 C8 C5 -4.3(3) . . . . ?
C5 C8 C9 C12 -2.9(4) . . . . ?
C7 C8 C9 C12 169.4(3) . . . . ?
C5 C8 C9 C10 178.7(3) . . . . ?
C7 C8 C9 C10 -9.0(5) . . . . ?
C8 C9 C10 O5 -3.9(5) . . . . ?
C12 C9 C10 O5 177.5(3) . . . . ?
C8 C9 C10 N3 177.0(3) . . . . ?
C12 C9 C10 N3 -1.6(3) . . . . ?
O5 C10 N3 C11 -179.3(3) . . . . ?
C9 C10 N3 C11 -0.1(3) . . . . ?
O5 C10 N3 C27 3.1(5) . . . . ?
C9 C10 N3 C27 -177.8(3) . . . . ?
C10 N3 C11 O6 -177.4(3) . . . . ?
C27 N3 C11 O6 0.3(4) . . . . ?
C10 N3 C11 C12 1.7(3) . . . . ?
C27 N3 C11 C12 179.4(3) . . . . ?
C4 C1 C12 C9 0.6(4) . . . . ?
C2 C1 C12 C9 -172.6(3) . . . . ?
C4 C1 C12 C11 177.0(3) . . . . ?
C2 C1 C12 C11 3.8(5) . . . . ?
C8 C9 C12 C1 1.0(4) . . . . ?
C10 C9 C12 C1 179.8(2) . . . . ?
C8 C9 C12 C11 -176.2(2) . . . . ?
C10 C9 C12 C11 2.6(3) . . . . ?
O6 C11 C12 C1 -0.3(5) . . . . ?
N3 C11 C12 C1 -179.4(3) . . . . ?
O6 C11 C12 C9 176.4(3) . . . . ?
N3 C11 C12 C9 -2.7(3) . . . . ?
C2 N1 C13 C14 -100.2(3) . . . . ?
C3 N1 C13 C14 84.1(4) . . . . ?
N1 C13 C14 C19 -115.8(3) . . . . ?
N1 C13 C14 C15 65.1(4) . . . . ?
C19 C14 C15 C16 2.1(5) . . . . ?
C13 C14 C15 C16 -178.8(3) . . . . ?
C14 C15 C16 C17 -1.1(5) . . . . ?
C15 C16 C17 C18 -1.3(6) . . . . ?
C16 C17 C18 C19 2.6(6) . . . . ?
C15 C14 C19 C18 -0.7(5) . . . . ?
C13 C14 C19 C18 -179.8(3) . . . . ?
C17 C18 C19 C14 -1.7(6) . . . . ?
C6 N2 C20 C21 -98.7(3) . . . . ?
C7 N2 C20 C21 91.9(3) . . . . ?
N2 C20 C21 C22 93.4(3) . . . . ?
N2 C20 C21 C26 -88.6(3) . . . . ?
C26 C21 C22 C23 0.3(4) . . . . ?
C20 C21 C22 C23 178.4(2) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C22 C21 C26 C25 0.3(4) . . . . ?
C20 C21 C26 C25 -177.7(2) . . . . ?
C24 C25 C26 C21 -1.0(4) . . . . ?
C10 N3 C27 C28 109.6(3) . . . . ?
C11 N3 C27 C28 -67.8(4) . . . . ?
N3 C27 C28 C29 123.9(3) . . . . ?
N3 C27 C28 C33 -56.2(4) . . . . ?
C33 C28 C29 C30 -0.4(5) . . . . ?
C27 C28 C29 C30 179.5(3) . . . . ?
C28 C29 C30 C31 1.6(5) . . . . ?
C29 C30 C31 C32 -1.2(5) . . . . ?
C30 C31 C32 C33 -0.3(5) . . . . ?
C31 C32 C33 C28 1.4(5) . . . . ?
C29 C28 C33 C32 -1.1(5) . . . . ?
C27 C28 C33 C32 179.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.154
####################################################################### 
# 
# 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_H-chlorobenzene
_database_code_depnum_ccdc_archive 'CCDC 1557863'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H21 N3 O6, C6 H5 Cl'
_chemical_formula_sum            'C39 H26 Cl N3 O6'
_chemical_formula_weight         668.08

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.2723(14)
_cell_length_b                   11.2723(14)
_cell_length_c                   42.445(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4670.7(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    24244
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      30.3

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2076
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21361
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2393
_reflns_number_gt                2231
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0649P)²+8.2932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2393
_refine_ls_number_parameters     178
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0907
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1867
_refine_ls_goodness_of_fit_ref   1.330
_refine_ls_restrained_S_all      1.321
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5067(3) 0.4681(3) 0.13144(6) 0.0308(6) Uani 1 1 d . . .
N1 N 0.3759(2) 0.3533(2) 0.12909(5) 0.0306(5) Uani 1 1 d . . .
C2 C 0.3751(3) 0.2293(3) 0.13158(6) 0.0283(6) Uani 1 1 d . . .
C3 C 0.5239(2) 0.2682(3) 0.13438(5) 0.0256(5) Uani 1 1 d . . .
C4 C 0.6033(3) 0.4122(2) 0.13444(5) 0.0256(5) Uani 1 1 d . . .
O1 O 0.5322(2) 0.58543(19) 0.13116(5) 0.0398(5) Uani 1 1 d . . .
O2 O 0.27348(18) 0.11751(19) 0.13152(4) 0.0353(5) Uani 1 1 d . . .
C5 C 0.2513(3) 0.3615(3) 0.12328(7) 0.0345(6) Uani 1 1 d . . .
H5 H 0.2641 0.4490 0.1317 0.041 Uiso 1 1 calc R . .
H5A H 0.1729 0.2856 0.1344 0.041 Uiso 1 1 calc R . .
C6 C 0.2201(3) 0.3526(3) 0.08840(7) 0.0353(6) Uani 1 1 d . . .
C7 C 0.3009(3) 0.4613(3) 0.06829(8) 0.0461(8) Uani 1 1 d . . .
H7 H 0.3747 0.5432 0.0767 0.055 Uiso 1 1 calc R . .
C8 C 0.2743(4) 0.4511(4) 0.03609(8) 0.0553(9) Uani 1 1 d . . .
H8 H 0.3309 0.5252 0.0226 0.066 Uiso 1 1 calc R . .
C9 C 0.1667(4) 0.3342(4) 0.02384(8) 0.0584(9) Uani 1 1 d . . .
H9 H 0.1476 0.3279 0.0019 0.070 Uiso 1 1 calc R . .
C10 C 0.0862(4) 0.2258(4) 0.04349(9) 0.0620(10) Uani 1 1 d . . .
H10 H 0.0120 0.1446 0.0350 0.074 Uiso 1 1 calc R . .
C11 C 0.1129(3) 0.2347(3) 0.07568(8) 0.0485(8) Uani 1 1 d . . .
H11 H 0.0571 0.1593 0.0890 0.058 Uiso 1 1 calc R . .
Cl1 Cl 0.6482(4) 0.5479(3) 0.05610(7) 0.0690(9) Uani 0.33 1 d P A -1
C12 C 0.6702(9) 0.4073(8) 0.05289(14) 0.0538(13) Uani 0.33 1 d PGU A -1
C13 C 0.5590(7) 0.2748(9) 0.05335(16) 0.0542(13) Uani 0.33 1 d PGU A -1
H13 H 0.4684 0.2602 0.0540 0.065 Uiso 0.33 1 calc PR A -1
C14 C 0.5803(8) 0.1635(7) 0.0528(2) 0.0550(13) Uani 0.33 1 d PGU A -1
H14 H 0.5043 0.0729 0.0531 0.066 Uiso 0.33 1 calc PR A -1
C15 C 0.7128(9) 0.1848(8) 0.05187(17) 0.0545(13) Uani 0.33 1 d PGU A -1
H15 H 0.7274 0.1088 0.0515 0.065 Uiso 0.33 1 calc PR A -1
C16 C 0.8241(7) 0.3174(9) 0.05141(18) 0.0546(13) Uani 0.33 1 d PGU A -1
H16 H 0.9146 0.3320 0.0507 0.065 Uiso 0.33 1 calc PR A -1
C17 C 0.8028(8) 0.4287(7) 0.0519(2) 0.0542(13) Uani 0.33 1 d PGU A -1
H17 H 0.8788 0.5193 0.0516 0.065 Uiso 0.33 1 calc PR A -1


_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 O1 1.205(3) . ?
C1 N1 1.397(3) . ?
C1 C4 1.511(3) . ?
N1 C2 1.396(3) . ?
N1 C5 1.473(3) . ?
C2 O2 1.207(3) . ?
C2 C3 1.512(3) . ?
C3 C4 1.379(3) 2_655 ?
C3 C4 1.408(3) . ?
C4 C3 1.379(3) 3_665 ?
C5 C6 1.513(4) . ?
C6 C11 1.383(4) . ?
C6 C7 1.394(4) . ?
C7 C8 1.392(5) . ?
C8 C9 1.370(5) . ?
C9 C10 1.380(5) . ?
C10 C11 1.392(5) . ?
Cl1 C12 1.727(6) . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 125.3(2) . . ?
O1 C1 C4 129.2(2) . . ?
N1 C1 C4 105.5(2) . . ?
C1 N1 C2 113.4(2) . . ?
C1 N1 C5 123.5(2) . . ?
C2 N1 C5 123.1(2) . . ?
O2 C2 N1 125.0(2) . . ?
O2 C2 C3 129.7(2) . . ?
N1 C2 C3 105.4(2) . . ?
C4 C3 C4 119.8(2) 2_655 . ?
C4 C3 C2 132.2(2) 2_655 . ?
C4 C3 C2 107.9(2) . . ?
C3 C4 C3 120.2(2) 3_665 . ?
C3 C4 C1 131.7(2) 3_665 . ?
C3 C4 C1 107.8(2) . . ?
N1 C5 C6 110.9(2) . . ?
C11 C6 C7 118.6(3) . . ?
C11 C6 C5 120.5(3) . . ?
C7 C6 C5 120.8(3) . . ?
C8 C7 C6 120.6(3) . . ?
C9 C8 C7 120.2(3) . . ?
C8 C9 C10 119.7(3) . . ?
C9 C10 C11 120.4(3) . . ?
C6 C11 C10 120.4(3) . . ?
C13 C12 C17 120.0 . . ?
C13 C12 Cl1 121.3(5) . . ?
C17 C12 Cl1 118.6(5) . . ?
C14 C13 C12 120.0 . . ?
C15 C14 C13 120.0 . . ?
C14 C15 C16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C16 C17 C12 120.0 . . ?

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
O1 C1 N1 C2 -177.1(3) . . . . ?
C4 C1 N1 C2 2.6(3) . . . . ?
O1 C1 N1 C5 5.3(4) . . . . ?
C4 C1 N1 C5 -175.0(2) . . . . ?
C1 N1 C2 O2 176.8(2) . . . . ?
C5 N1 C2 O2 -5.5(4) . . . . ?
C1 N1 C2 C3 -2.9(3) . . . . ?
C5 N1 C2 C3 174.8(2) . . . . ?
O2 C2 C3 C4 7.5(5) . . . 2_655 ?
N1 C2 C3 C4 -172.8(3) . . . 2_655 ?
O2 C2 C3 C4 -177.8(3) . . . . ?
N1 C2 C3 C4 1.9(3) . . . . ?
C4 C3 C4 C3 0.4(5) 2_655 . . 3_665 ?
C2 C3 C4 C3 -175.11(17) . . . 3_665 ?
C4 C3 C4 C1 175.06(18) 2_655 . . . ?
C2 C3 C4 C1 -0.4(3) . . . . ?
O1 C1 C4 C3 -7.7(5) . . . 3_665 ?
N1 C1 C4 C3 172.6(3) . . . 3_665 ?
O1 C1 C4 C3 178.4(3) . . . . ?
N1 C1 C4 C3 -1.2(3) . . . . ?
C1 N1 C5 C6 92.7(3) . . . . ?
C2 N1 C5 C6 -84.7(3) . . . . ?
N1 C5 C6 C11 106.3(3) . . . . ?
N1 C5 C6 C7 -71.8(3) . . . . ?
C11 C6 C7 C8 -0.2(4) . . . . ?
C5 C6 C7 C8 178.0(3) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C7 C8 C9 C10 -1.1(6) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C7 C6 C11 C10 -0.4(5) . . . . ?
C5 C6 C11 C10 -178.6(3) . . . . ?
C9 C10 C11 C6 0.3(6) . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
Cl1 C12 C13 C14 -175.7(5) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C12 0.0 . . . . ?
C13 C12 C17 C16 0.0 . . . . ?
Cl1 C12 C17 C16 175.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_H-pyridine
_database_code_depnum_ccdc_archive 'CCDC 1557865'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H21 N3 O6, C5 H5 N'
_chemical_formula_sum            'C38 H26 N4 O6'
_chemical_formula_weight         634.63

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.1856(6)
_cell_length_b                   11.1856(6)
_cell_length_c                   42.522(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4607.5(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4162
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      30.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1980
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17928
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1910
_reflns_number_gt                1744
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+6.6243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1910
_refine_ls_number_parameters     211
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.005

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 0.73179(16) 0.47690(16) 0.13478(4) 0.0213(4) Uani 1 1 d . . .
C2 C 0.58712(16) 0.39734(16) 0.13483(4) 0.0217(4) Uani 1 1 d . . .
C3 C 0.53149(17) 0.49396(17) 0.13159(4) 0.0253(4) Uani 1 1 d . . .
N1 N 0.64665(15) 0.62507(14) 0.12896(3) 0.0264(4) Uani 1 1 d . . .
C4 C 0.77083(17) 0.62618(17) 0.13176(4) 0.0242(4) Uani 1 1 d . . .
O1 O 0.41305(13) 0.46802(14) 0.13106(3) 0.0354(4) Uani 1 1 d . . .
O2 O 0.88351(12) 0.72848(12) 0.13169(3) 0.0312(3) Uani 1 1 d . . .
C5 C 0.6380(2) 0.75009(18) 0.12284(4) 0.0311(4) Uani 1 1 d . . .
H5 H 0.7141 0.8295 0.1339 0.037 Uiso 1 1 calc R . .
H5A H 0.5496 0.7371 0.1312 0.037 Uiso 1 1 calc R . .
C6 C 0.64712(19) 0.78114(19) 0.08793(4) 0.0308(4) Uani 1 1 d . . .
C7 C 0.5396(2) 0.6965(2) 0.06775(5) 0.0430(5) Uani 1 1 d . . .
H7 H 0.4591 0.6190 0.0760 0.052 Uiso 1 1 calc R . .
C8 C 0.5488(2) 0.7241(3) 0.03594(5) 0.0513(6) Uani 1 1 d . . .
H8 H 0.4756 0.6646 0.0223 0.062 Uiso 1 1 calc R . .
C9 C 0.6640(3) 0.8377(3) 0.02379(5) 0.0506(6) Uani 1 1 d . . .
H9 H 0.6695 0.8579 0.0020 0.061 Uiso 1 1 calc R . .
C10 C 0.7711(3) 0.9218(3) 0.04367(5) 0.0510(6) Uani 1 1 d . . .
H10 H 0.8509 0.9997 0.0354 0.061 Uiso 1 1 calc R . .
C11 C 0.7630(2) 0.8935(2) 0.07552(5) 0.0405(5) Uani 1 1 d . . .
H11 H 0.8375 0.9518 0.0889 0.049 Uiso 1 1 calc R . .
N2 N 0.659(3) 0.219(2) 0.0533(6) 0.0586(15) Uani 0.17 1 d PGU A -1
C12 C 0.795(3) 0.327(3) 0.0509(7) 0.0586(15) Uani 0.17 1 d PGU A -1
H12 H 0.8676 0.3069 0.0489 0.070 Uiso 0.17 1 calc PR A -1
C13 C 0.823(2) 0.463(3) 0.0513(9) 0.0590(15) Uani 0.17 1 d PGU A -1
H13 H 0.9161 0.5360 0.0496 0.071 Uiso 0.17 1 calc PR A -1
C14 C 0.717(2) 0.4915(17) 0.0541(8) 0.0589(15) Uani 0.17 1 d PGU A -1
H14 H 0.7362 0.5845 0.0544 0.071 Uiso 0.17 1 calc PR A -1
C15 C 0.581(2) 0.3842(14) 0.0566(6) 0.0588(15) Uani 0.17 1 d PGU A -1
H15 H 0.5079 0.4039 0.0585 0.071 Uiso 0.17 1 calc PR A -1
C16 C 0.552(2) 0.2481(15) 0.0562(6) 0.0584(15) Uani 0.17 1 d PGU A -1
H16 H 0.4595 0.1747 0.0579 0.070 Uiso 0.17 1 calc PR A -1
N3 N 0.7460(19) 0.5186(15) 0.0535(5) 0.0590(15) Uani 0.17 1 d PGU B -2
C17 C 0.6058(19) 0.4222(15) 0.0534(4) 0.0589(15) Uani 0.17 1 d PGU B -2
H17 H 0.5399 0.4521 0.0539 0.071 Uiso 0.17 1 calc PR B -2
C18 C 0.562(2) 0.2820(14) 0.0527(4) 0.0586(15) Uani 0.17 1 d PGU B -2
H18 H 0.4662 0.2160 0.0526 0.070 Uiso 0.17 1 calc PR B -2
C19 C 0.659(3) 0.2382(18) 0.0520(6) 0.0586(15) Uani 0.17 1 d PGU B -2
H19 H 0.6286 0.1424 0.0515 0.070 Uiso 0.17 1 calc PR B -2
C20 C 0.799(3) 0.335(3) 0.0520(8) 0.0586(15) Uani 0.17 1 d PGU B -2
H20 H 0.8647 0.3048 0.0515 0.070 Uiso 0.17 1 calc PR B -2
C21 C 0.842(2) 0.475(2) 0.0528(8) 0.0589(15) Uani 0.17 1 d PGU B -2
H21 H 0.9383 0.5408 0.0528 0.071 Uiso 0.17 1 calc PR B -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(2) 3_665 ?
C1 C2 1.404(2) . ?
C1 C4 1.505(2) . ?
C2 C1 1.382(2) 2_655 ?
C2 C3 1.499(2) . ?
C3 O1 1.206(2) . ?
C3 N1 1.390(2) . ?
N1 C4 1.388(2) . ?
N1 C5 1.472(2) . ?
C4 O2 1.207(2) . ?
C5 C6 1.516(2) . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C11 1.382(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.380(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
N2 C12 1.3900 . ?
N2 C16 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N3 C17 1.3900 . ?
N3 C21 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 H21 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 C1 C2 120.04(16) 3_665 . ?
C2 C1 C4 131.87(15) 3_665 . ?
C2 C1 C4 107.85(14) . . ?
C1 C2 C1 119.96(16) 2_655 . ?
C1 C2 C3 131.95(15) 2_655 . ?
C1 C2 C3 107.77(14) . . ?
O1 C3 N1 125.38(15) . . ?
O1 C3 C2 129.06(16) . . ?
N1 C3 C2 105.56(13) . . ?
C4 N1 C3 113.44(13) . . ?
C4 N1 C5 123.19(14) . . ?
C3 N1 C5 123.35(14) . . ?
O2 C4 N1 125.07(15) . . ?
O2 C4 C1 129.66(15) . . ?
N1 C4 C1 105.27(13) . . ?
N1 C5 C6 111.21(14) . . ?
N1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
H5 C5 H5A 108.0 . . ?
C11 C6 C7 118.77(18) . . ?
C11 C6 C5 120.51(17) . . ?
C7 C6 C5 120.72(17) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 120.4(2) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C12 N2 C16 120.0 . . ?
C13 C12 N2 120.0 . . ?
C13 C12 H12 120.0 . . ?
N2 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 N2 120.0 . . ?
C15 C16 H16 120.0 . . ?
N2 C16 H16 120.0 . . ?
C17 N3 C21 120.0 . . ?
N3 C17 C18 120.0 . . ?
N3 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 N3 120.0 . . ?
C20 C21 H21 120.0 . . ?
N3 C21 H21 120.0 . . ?

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
C2 C1 C2 C1 -0.3(3) 3_665 . . 2_655 ?
C4 C1 C2 C1 174.72(11) . . . 2_655 ?
C2 C1 C2 C3 -174.58(11) 3_665 . . . ?
C4 C1 C2 C3 0.46(17) . . . . ?
C1 C2 C3 O1 7.8(3) 2_655 . . . ?
C1 C2 C3 O1 -178.88(17) . . . . ?
C1 C2 C3 N1 -171.79(16) 2_655 . . . ?
C1 C2 C3 N1 1.53(17) . . . . ?
O1 C3 N1 C4 177.21(16) . . . . ?
C2 C3 N1 C4 -3.17(18) . . . . ?
O1 C3 N1 C5 -4.6(3) . . . . ?
C2 C3 N1 C5 175.05(14) . . . . ?
C3 N1 C4 O2 -176.44(15) . . . . ?
C5 N1 C4 O2 5.3(3) . . . . ?
C3 N1 C4 C1 3.44(18) . . . . ?
C5 N1 C4 C1 -174.79(14) . . . . ?
C2 C1 C4 O2 -8.2(3) 3_665 . . . ?
C2 C1 C4 O2 177.59(16) . . . . ?
C2 C1 C4 N1 171.95(16) 3_665 . . . ?
C2 C1 C4 N1 -2.28(17) . . . . ?
C4 N1 C5 C6 84.9(2) . . . . ?
C3 N1 C5 C6 -93.10(19) . . . . ?
N1 C5 C6 C11 -109.72(19) . . . . ?
N1 C5 C6 C7 69.8(2) . . . . ?
C11 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C8 -179.26(19) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C7 C6 C11 C10 0.6(3) . . . . ?
C5 C6 C11 C10 -179.92(18) . . . . ?
C9 C10 C11 C6 -0.4(3) . . . . ?
C16 N2 C12 C13 0.0 . . . . ?
N2 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 N2 0.0 . . . . ?
C12 N2 C16 C15 0.0 . . . . ?
C21 N3 C17 C18 0.0 . . . . ?
N3 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 N3 0.0 . . . . ?
C17 N3 C21 C20 0.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_F-PhNO2
_database_code_depnum_ccdc_archive 'CCDC 1557872'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H18 F3 N3 O6, C6 H5 N O2'
_chemical_formula_sum            'C39 H23 F3 N4 O8'
_chemical_formula_weight         732.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.924(5)
_cell_length_b                   10.644(4)
_cell_length_c                   25.903(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.568(5)
_cell_angle_gamma                90.00
_cell_volume                     3259(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5982
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      30.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         51252
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37544
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.50
_reflns_number_total             6061
_reflns_number_gt                5530
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6061
_refine_ls_number_parameters     579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.2165
_refine_ls_wR_factor_gt          0.2047
_refine_ls_goodness_of_fit_ref   1.393
_refine_ls_restrained_S_all      1.393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1838(3) 0.0827(4) -0.00936(14) 0.0335(9) Uani 1 1 d . . .
C2 C 0.1854(3) 0.2113(4) -0.01501(15) 0.0371(9) Uani 1 1 d . . .
H1 H 0.225(4) 0.252(4) -0.0416(18) 0.047(12) Uiso 1 1 d . . .
C3 C 0.1356(3) 0.2839(4) 0.01989(14) 0.0317(8) Uani 1 1 d . . .
H2 H 0.136(3) 0.368(4) 0.0194(15) 0.034(11) Uiso 1 1 d . . .
C4 C 0.0873(3) 0.2284(3) 0.06057(13) 0.0233(7) Uani 1 1 d . . .
C5 C 0.0872(3) 0.0988(3) 0.06477(14) 0.0275(8) Uani 1 1 d . . .
H3 H 0.052(3) 0.063(3) 0.0941(15) 0.027(9) Uiso 1 1 d . . .
C6 C 0.1348(3) 0.0240(4) 0.02906(14) 0.0303(8) Uani 1 1 d . . .
H4 H 0.132(4) -0.061(4) 0.0316(17) 0.050(13) Uiso 1 1 d . . .
C7 C 0.0380(3) 0.3117(3) 0.09935(14) 0.0238(7) Uani 1 1 d . . .
H5 H -0.013(3) 0.371(3) 0.0832(13) 0.021(9) Uiso 1 1 d . . .
H6 H -0.001(3) 0.258(3) 0.1239(14) 0.019(8) Uiso 1 1 d . . .
N1 N 0.1299(2) 0.3816(2) 0.13104(11) 0.0231(6) Uani 1 1 d . . .
C8 C 0.1582(3) 0.5060(3) 0.12222(12) 0.0221(7) Uani 1 1 d . . .
C9 C 0.2575(3) 0.5351(3) 0.16295(12) 0.0214(7) Uani 1 1 d . . .
C10 C 0.2854(3) 0.4249(3) 0.19099(12) 0.0202(7) Uani 1 1 d . . .
C11 C 0.2020(3) 0.3247(3) 0.17059(12) 0.0216(7) Uani 1 1 d . . .
O1 O 0.11084(19) 0.5735(2) 0.08824(9) 0.0276(6) Uani 1 1 d . . .
O2 O 0.19603(19) 0.2172(2) 0.18450(9) 0.0243(5) Uani 1 1 d . . .
C12 C 0.5897(3) 1.1874(3) 0.11035(15) 0.0327(9) Uani 1 1 d . . .
C13 C 0.6309(3) 1.1316(4) 0.15704(15) 0.0349(9) Uani 1 1 d . . .
H7 H 0.715(4) 1.141(4) 0.1710(16) 0.042(11) Uiso 1 1 d . . .
C14 C 0.5553(3) 1.0671(3) 0.18391(15) 0.0316(8) Uani 1 1 d . . .
H8 H 0.587(3) 1.023(4) 0.2186(17) 0.042(11) Uiso 1 1 d . . .
C15 C 0.4421(3) 1.0571(3) 0.16386(13) 0.0238(7) Uani 1 1 d . . .
C16 C 0.4033(3) 1.1119(3) 0.11615(14) 0.0292(8) Uani 1 1 d . . .
H9 H 0.316(3) 1.109(4) 0.1015(17) 0.048(12) Uiso 1 1 d . . .
C17 C 0.4773(3) 1.1788(3) 0.08864(15) 0.0324(8) Uani 1 1 d . . .
H10 H 0.448(3) 1.218(4) 0.0517(17) 0.040(11) Uiso 1 1 d . . .
C18 C 0.3597(3) 0.9905(3) 0.19457(15) 0.0274(8) Uani 1 1 d . . .
H11 H 0.378(3) 1.018(3) 0.2316(15) 0.026(9) Uiso 1 1 d . . .
H12 H 0.278(3) 1.013(3) 0.1795(13) 0.021(9) Uiso 1 1 d . . .
N2 N 0.3662(2) 0.8528(2) 0.19292(11) 0.0238(6) Uani 1 1 d . . .
C19 C 0.4370(3) 0.7814(3) 0.22904(13) 0.0241(7) Uani 1 1 d . . .
C20 C 0.4014(3) 0.6470(3) 0.21888(13) 0.0221(7) Uani 1 1 d . . .
C21 C 0.3145(3) 0.6459(3) 0.17687(12) 0.0203(7) Uani 1 1 d . . .
C22 C 0.2903(3) 0.7802(3) 0.15982(13) 0.0226(7) Uani 1 1 d . . .
O3 O 0.5080(2) 0.8251(2) 0.26193(10) 0.0298(6) Uani 1 1 d . . .
O4 O 0.2180(2) 0.8214(2) 0.12707(9) 0.0287(6) Uani 1 1 d . . .
C23 C 0.7797(3) 0.0392(3) 0.30883(13) 0.0287(8) Uani 1 1 d . . .
C24 C 0.7090(3) 0.0095(3) 0.34522(14) 0.0297(8) Uani 1 1 d . . .
H13 H 0.707(3) -0.074(4) 0.3590(16) 0.037(10) Uiso 1 1 d . . .
C25 C 0.6360(3) 0.1033(3) 0.35867(14) 0.0263(8) Uani 1 1 d . . .
H14 H 0.586(3) 0.085(3) 0.3832(14) 0.018(8) Uiso 1 1 d . . .
C26 C 0.6366(3) 0.2226(3) 0.33674(13) 0.0228(7) Uani 1 1 d . . .
C27 C 0.7112(3) 0.2479(3) 0.30057(13) 0.0250(8) Uani 1 1 d . . .
H15 H 0.717(3) 0.332(3) 0.2823(15) 0.031(10) Uiso 1 1 d . . .
C28 C 0.7824(3) 0.1560(3) 0.28614(14) 0.0281(8) Uani 1 1 d . . .
H16 H 0.837(3) 0.173(4) 0.2596(17) 0.042(11) Uiso 1 1 d . . .
C29 C 0.5572(3) 0.3237(3) 0.35233(13) 0.0237(7) Uani 1 1 d . . .
H17 H 0.501(3) 0.292(3) 0.3760(14) 0.024(9) Uiso 1 1 d . . .
H18 H 0.601(3) 0.393(4) 0.3733(16) 0.044(11) Uiso 1 1 d . . .
N3 N 0.4963(2) 0.3874(3) 0.30673(10) 0.0225(6) Uani 1 1 d . . .
C30 C 0.4155(3) 0.3274(3) 0.27164(12) 0.0220(7) Uani 1 1 d . . .
C31 C 0.3721(3) 0.4267(3) 0.23259(12) 0.0207(7) Uani 1 1 d . . .
C32 C 0.4306(3) 0.5386(3) 0.24602(12) 0.0209(7) Uani 1 1 d . . .
C33 C 0.5127(3) 0.5133(3) 0.29435(13) 0.0217(7) Uani 1 1 d . . .
O5 O 0.38774(19) 0.2184(2) 0.27419(9) 0.0254(5) Uani 1 1 d . . .
O6 O 0.58010(19) 0.5832(2) 0.31891(9) 0.0265(5) Uani 1 1 d . . .
C34 C 0.1528(3) 0.1597(3) 0.47175(13) 0.0270(8) Uani 1 1 d . . .
C35 C 0.1140(3) 0.2797(4) 0.46004(15) 0.0315(8) Uani 1 1 d . . .
H19 H 0.154(3) 0.356(4) 0.4738(16) 0.041(11) Uiso 1 1 d . . .
C36 C 0.0080(3) 0.2940(4) 0.43026(15) 0.0338(9) Uani 1 1 d . . .
H20 H -0.026(3) 0.390(4) 0.4210(17) 0.049(12) Uiso 1 1 d . . .
C37 C -0.0528(3) 0.1877(4) 0.41296(15) 0.0370(9) Uani 1 1 d . . .
H21 H -0.125(3) 0.200(4) 0.3917(17) 0.041(11) Uiso 1 1 d . . .
C38 C -0.0114(3) 0.0680(4) 0.42418(15) 0.0374(9) Uani 1 1 d . . .
H22 H -0.055(4) -0.008(4) 0.4141(17) 0.052(13) Uiso 1 1 d . . .
C39 C 0.0938(3) 0.0535(4) 0.45460(15) 0.0351(9) Uani 1 1 d . . .
H23 H 0.127(4) -0.035(4) 0.4617(17) 0.050(12) Uiso 1 1 d . . .
N4 N 0.2631(2) 0.1448(3) 0.50471(11) 0.0284(7) Uani 1 1 d . . .
O7 O 0.3271(2) 0.2346(2) 0.51017(10) 0.0362(6) Uani 1 1 d . . .
O8 O 0.2831(2) 0.0423(2) 0.52624(10) 0.0342(6) Uani 1 1 d . . .
F1 F 0.85251(17) -0.05169(19) 0.29571(8) 0.0368(5) Uani 1 1 d . . .
F2 F 0.6618(2) 1.2551(2) 0.08495(9) 0.0458(6) Uani 1 1 d . . .
F3 F 0.2331(2) 0.0111(2) -0.04415(8) 0.0470(6) 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 C6 1.369(5) . ?
C1 F3 1.371(4) . ?
C1 C2 1.376(6) . ?
C2 C3 1.382(6) . ?
C2 H1 0.98(5) . ?
C3 C4 1.397(5) . ?
C3 H2 0.89(4) . ?
C4 C5 1.384(5) . ?
C4 C7 1.516(5) . ?
C5 C6 1.396(5) . ?
C5 H3 0.99(4) . ?
C6 H4 0.91(4) . ?
C7 N1 1.480(4) . ?
C7 H5 0.94(4) . ?
C7 H6 1.01(4) . ?
N1 C11 1.387(4) . ?
N1 C8 1.393(4) . ?
C8 O1 1.216(4) . ?
C8 C9 1.510(4) . ?
C9 C21 1.386(4) . ?
C9 C10 1.397(4) . ?
C10 C31 1.392(5) . ?
C10 C11 1.505(4) . ?
C11 O2 1.204(4) . ?
C12 F2 1.357(4) . ?
C12 C13 1.379(5) . ?
C12 C17 1.386(5) . ?
C13 C14 1.391(5) . ?
C13 H7 1.03(4) . ?
C14 C15 1.385(5) . ?
C14 H8 1.04(4) . ?
C15 C16 1.390(5) . ?
C15 C18 1.519(5) . ?
C16 C17 1.400(5) . ?
C16 H9 1.06(4) . ?
C17 H10 1.06(4) . ?
C18 N2 1.469(4) . ?
C18 H11 1.00(4) . ?
C18 H12 1.02(3) . ?
N2 C22 1.395(4) . ?
N2 C19 1.400(4) . ?
C19 O3 1.212(4) . ?
C19 C20 1.506(4) . ?
C20 C32 1.372(4) . ?
C20 C21 1.400(5) . ?
C21 C22 1.512(4) . ?
C22 O4 1.209(4) . ?
C23 F1 1.373(4) . ?
C23 C28 1.377(5) . ?
C23 C24 1.381(5) . ?
C24 C25 1.398(5) . ?
C24 H13 0.96(4) . ?
C25 C26 1.391(5) . ?
C25 H14 0.95(3) . ?
C26 C27 1.400(5) . ?
C26 C29 1.522(5) . ?
C27 C28 1.379(5) . ?
C27 H15 1.02(4) . ?
C28 H16 1.02(4) . ?
C29 N3 1.469(4) . ?
C29 H17 1.03(4) . ?
C29 H18 1.02(4) . ?
N3 C30 1.390(4) . ?
N3 C33 1.398(4) . ?
C30 O5 1.211(4) . ?
C30 C31 1.507(4) . ?
C31 C32 1.401(4) . ?
C32 C33 1.508(4) . ?
C33 O6 1.213(4) . ?
C34 C39 1.374(5) . ?
C34 C35 1.379(5) . ?
C34 N4 1.479(4) . ?
C35 C36 1.399(5) . ?
C35 H19 0.99(4) . ?
C36 C37 1.386(6) . ?
C36 H20 1.12(4) . ?
C37 C38 1.383(6) . ?
C37 H21 0.97(4) . ?
C38 C39 1.399(5) . ?
C38 H22 0.97(5) . ?
C39 H23 1.03(4) . ?
N4 O7 1.219(4) . ?
N4 O8 1.234(4) . ?

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
C6 C1 F3 119.0(3) . . ?
C6 C1 C2 123.0(3) . . ?
F3 C1 C2 118.0(3) . . ?
C1 C2 C3 118.3(4) . . ?
C1 C2 H1 122(2) . . ?
C3 C2 H1 120(3) . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H2 123(3) . . ?
C4 C3 H2 116(3) . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 C7 121.8(3) . . ?
C3 C4 C7 119.1(3) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H3 117(2) . . ?
C6 C5 H3 122(2) . . ?
C1 C6 C5 118.1(4) . . ?
C1 C6 H4 122(3) . . ?
C5 C6 H4 120(3) . . ?
N1 C7 C4 109.8(3) . . ?
N1 C7 H5 107(2) . . ?
C4 C7 H5 113(2) . . ?
N1 C7 H6 107.7(19) . . ?
C4 C7 H6 109.9(19) . . ?
H5 C7 H6 109(3) . . ?
C11 N1 C8 113.3(3) . . ?
C11 N1 C7 122.1(3) . . ?
C8 N1 C7 124.4(3) . . ?
O1 C8 N1 125.5(3) . . ?
O1 C8 C9 129.2(3) . . ?
N1 C8 C9 105.4(3) . . ?
C21 C9 C10 120.3(3) . . ?
C21 C9 C8 132.0(3) . . ?
C10 C9 C8 107.6(3) . . ?
C31 C10 C9 119.5(3) . . ?
C31 C10 C11 132.1(3) . . ?
C9 C10 C11 108.1(3) . . ?
O2 C11 N1 125.5(3) . . ?
O2 C11 C10 129.0(3) . . ?
N1 C11 C10 105.5(3) . . ?
F2 C12 C13 118.6(3) . . ?
F2 C12 C17 118.6(3) . . ?
C13 C12 C17 122.8(3) . . ?
C12 C13 C14 118.1(3) . . ?
C12 C13 H7 119(2) . . ?
C14 C13 H7 123(2) . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H8 121(2) . . ?
C13 C14 H8 118(2) . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 C18 120.4(3) . . ?
C16 C15 C18 119.9(3) . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H9 120(2) . . ?
C17 C16 H9 119(2) . . ?
C12 C17 C16 117.9(3) . . ?
C12 C17 H10 122(2) . . ?
C16 C17 H10 120(2) . . ?
N2 C18 C15 114.2(3) . . ?
N2 C18 H11 108(2) . . ?
C15 C18 H11 107(2) . . ?
N2 C18 H12 105.9(19) . . ?
C15 C18 H12 109.6(19) . . ?
H11 C18 H12 112(3) . . ?
C22 N2 C19 113.3(3) . . ?
C22 N2 C18 122.5(3) . . ?
C19 N2 C18 123.5(3) . . ?
O3 C19 N2 124.5(3) . . ?
O3 C19 C20 130.0(3) . . ?
N2 C19 C20 105.5(3) . . ?
C32 C20 C21 120.2(3) . . ?
C32 C20 C19 131.5(3) . . ?
C21 C20 C19 107.9(3) . . ?
C9 C21 C20 119.8(3) . . ?
C9 C21 C22 131.3(3) . . ?
C20 C21 C22 108.2(3) . . ?
O4 C22 N2 125.1(3) . . ?
O4 C22 C21 129.7(3) . . ?
N2 C22 C21 105.1(3) . . ?
F1 C23 C28 118.6(3) . . ?
F1 C23 C24 118.1(3) . . ?
C28 C23 C24 123.3(3) . . ?
C23 C24 C25 117.5(3) . . ?
C23 C24 H13 121(2) . . ?
C25 C24 H13 121(2) . . ?
C26 C25 C24 120.8(3) . . ?
C26 C25 H14 120(2) . . ?
C24 C25 H14 119(2) . . ?
C25 C26 C27 119.1(3) . . ?
C25 C26 C29 120.0(3) . . ?
C27 C26 C29 120.9(3) . . ?
C28 C27 C26 120.9(3) . . ?
C28 C27 H15 115(2) . . ?
C26 C27 H15 124(2) . . ?
C23 C28 C27 118.3(3) . . ?
C23 C28 H16 120(2) . . ?
C27 C28 H16 122(2) . . ?
N3 C29 C26 111.8(3) . . ?
N3 C29 H17 109.8(19) . . ?
C26 C29 H17 113.9(19) . . ?
N3 C29 H18 105(2) . . ?
C26 C29 H18 111(2) . . ?
H17 C29 H18 105(3) . . ?
C30 N3 C33 113.3(3) . . ?
C30 N3 C29 122.7(3) . . ?
C33 N3 C29 124.0(3) . . ?
O5 C30 N3 125.1(3) . . ?
O5 C30 C31 129.6(3) . . ?
N3 C30 C31 105.3(3) . . ?
C10 C31 C32 119.9(3) . . ?
C10 C31 C30 131.6(3) . . ?
C32 C31 C30 108.3(3) . . ?
C20 C32 C31 120.2(3) . . ?
C20 C32 C33 132.0(3) . . ?
C31 C32 C33 107.6(3) . . ?
O6 C33 N3 124.8(3) . . ?
O6 C33 C32 129.7(3) . . ?
N3 C33 C32 105.5(3) . . ?
C39 C34 C35 123.2(3) . . ?
C39 C34 N4 118.5(3) . . ?
C35 C34 N4 118.3(3) . . ?
C34 C35 C36 118.4(4) . . ?
C34 C35 H19 123(2) . . ?
C36 C35 H19 118(2) . . ?
C37 C36 C35 119.0(4) . . ?
C37 C36 H20 121(2) . . ?
C35 C36 H20 120(2) . . ?
C38 C37 C36 121.8(4) . . ?
C38 C37 H21 121(2) . . ?
C36 C37 H21 118(2) . . ?
C37 C38 C39 119.2(4) . . ?
C37 C38 H22 123(3) . . ?
C39 C38 H22 118(3) . . ?
C34 C39 C38 118.3(4) . . ?
C34 C39 H23 122(2) . . ?
C38 C39 H23 120(2) . . ?
O7 N4 O8 124.1(3) . . ?
O7 N4 C34 118.5(3) . . ?
O8 N4 C34 117.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_F-toluene
_database_code_depnum_ccdc_archive 'CCDC 1557869'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H18 F3 N3 O6, C6 H8'
_chemical_formula_sum            'C40 H26 F3 N3 O6'
_chemical_formula_weight         701.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.152(4)
_cell_length_b                   11.305(4)
_cell_length_c                   15.563(6)
_cell_angle_alpha                88.785(16)
_cell_angle_beta                 69.158(11)
_cell_angle_gamma                62.289(10)
_cell_volume                     1598.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    93
_cell_measurement_reflns_used    4378
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21510
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         27.59
_reflns_number_total             7272
_reflns_number_gt                5575
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7272
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.00047(13) 0.12851(12) 0.89973(8) 0.0169(3) Uani 1 1 d . . .
C2 C 0.07938(13) 0.19115(12) 0.90225(8) 0.0172(3) Uani 1 1 d . . .
C3 C 0.01916(13) 0.33159(12) 0.90552(8) 0.0173(3) Uani 1 1 d . . .
C4 C -0.12073(13) 0.40764(12) 0.90628(8) 0.0171(3) Uani 1 1 d . . .
C5 C -0.20195(13) 0.34400(12) 0.90380(8) 0.0171(3) Uani 1 1 d . . .
C6 C -0.14202(13) 0.20573(12) 0.90043(8) 0.0174(3) Uani 1 1 d . . .
C7 C -0.19710(14) 0.11010(13) 0.89061(8) 0.0195(3) Uani 1 1 d . . .
N1 N -0.08232(11) -0.01938(10) 0.88313(7) 0.0196(2) Uani 1 1 d . . .
C8 C 0.03688(14) -0.01771(13) 0.89211(8) 0.0191(3) Uani 1 1 d . . .
O1 O -0.31237(10) 0.13390(9) 0.88854(7) 0.0264(2) Uani 1 1 d . . .
O2 O 0.14360(10) -0.11621(9) 0.89470(6) 0.0244(2) Uani 1 1 d . . .
C9 C 0.23498(14) 0.13378(13) 0.89511(8) 0.0204(3) Uani 1 1 d . . .
N2 N 0.25922(11) 0.24461(11) 0.89107(7) 0.0208(2) Uani 1 1 d . . .
C10 C 0.13504(14) 0.36736(13) 0.90054(8) 0.0191(3) Uani 1 1 d . . .
O3 O 0.32358(10) 0.01886(9) 0.89307(6) 0.0267(2) Uani 1 1 d . . .
O4 O 0.12952(10) 0.47653(9) 0.90315(6) 0.0241(2) Uani 1 1 d . . .
C11 C -0.20881(14) 0.55473(12) 0.90225(8) 0.0197(3) Uani 1 1 d . . .
N3 N -0.33745(11) 0.56986(10) 0.89730(7) 0.0203(2) Uani 1 1 d . . .
C12 C -0.34439(14) 0.44992(12) 0.89927(8) 0.0187(3) Uani 1 1 d . . .
O5 O -0.17943(10) 0.64476(9) 0.90270(6) 0.0248(2) Uani 1 1 d . . .
O6 O -0.44615(10) 0.43869(9) 0.89758(6) 0.0235(2) Uani 1 1 d . . .
C13 C -0.08843(15) -0.14414(12) 0.87070(9) 0.0215(3) Uani 1 1 d . . .
H13 H -0.1926 -0.1224 0.8941 0.026 Uiso 1 1 calc R . .
H13A H -0.0415 -0.2074 0.9083 0.026 Uiso 1 1 calc R . .
C14 C -0.01204(14) -0.21299(13) 0.76975(9) 0.0198(3) Uani 1 1 d . . .
C15 C -0.06614(15) -0.15223(14) 0.70356(9) 0.0252(3) Uani 1 1 d . . .
H15 H -0.1516 -0.0654 0.7216 0.030 Uiso 1 1 calc R . .
C16 C 0.00354(16) -0.21723(15) 0.61109(9) 0.0294(3) Uani 1 1 d . . .
H16 H -0.0328 -0.1759 0.5654 0.035 Uiso 1 1 calc R . .
C17 C 0.12580(16) -0.34229(15) 0.58777(9) 0.0292(3) Uani 1 1 d . . .
C18 C 0.18348(16) -0.40603(14) 0.65103(10) 0.0289(3) Uani 1 1 d . . .
H18 H 0.2687 -0.4931 0.6324 0.035 Uiso 1 1 calc R . .
C19 C 0.11362(15) -0.33949(13) 0.74269(9) 0.0248(3) Uani 1 1 d . . .
H19 H 0.1521 -0.3808 0.7875 0.030 Uiso 1 1 calc R . .
F1 F 0.19554(10) -0.40708(9) 0.49786(5) 0.0440(2) Uani 1 1 d . . .
C20 C 0.40374(14) 0.23108(14) 0.87387(9) 0.0232(3) Uani 1 1 d . . .
H20 H 0.4612 0.1494 0.8963 0.028 Uiso 1 1 calc R . .
H20A H 0.3904 0.3112 0.9091 0.028 Uiso 1 1 calc R . .
C21 C 0.48712(13) 0.21948(13) 0.77111(9) 0.0212(3) Uani 1 1 d . . .
C22 C 0.56177(15) 0.09616(14) 0.71111(10) 0.0261(3) Uani 1 1 d . . .
H22 H 0.5633 0.0180 0.7355 0.031 Uiso 1 1 calc R . .
C23 C 0.63414(15) 0.08567(14) 0.61602(10) 0.0288(3) Uani 1 1 d . . .
H23 H 0.6851 0.0014 0.5750 0.035 Uiso 1 1 calc R . .
C24 C 0.63018(15) 0.20004(15) 0.58295(9) 0.0273(3) Uani 1 1 d . . .
C25 C 0.55937(15) 0.32393(14) 0.63987(10) 0.0278(3) Uani 1 1 d . . .
H25 H 0.5599 0.4011 0.6148 0.033 Uiso 1 1 calc R . .
C26 C 0.48744(14) 0.33290(14) 0.73446(9) 0.0253(3) Uani 1 1 d . . .
H26 H 0.4376 0.4175 0.7750 0.030 Uiso 1 1 calc R . .
F2 F 0.70132(10) 0.19115(9) 0.48995(5) 0.0391(2) Uani 1 1 d . . .
C27 C -0.45212(14) 0.69721(12) 0.88682(9) 0.0234(3) Uani 1 1 d . . .
H27 H -0.4462 0.7745 0.9099 0.028 Uiso 1 1 calc R . .
H27A H -0.5501 0.7081 0.9254 0.028 Uiso 1 1 calc R . .
C28 C -0.43631(14) 0.70001(12) 0.78644(9) 0.0212(3) Uani 1 1 d . . .
C29 C -0.32464(15) 0.71784(13) 0.72182(10) 0.0264(3) Uani 1 1 d . . .
H29 H -0.2588 0.7296 0.7414 0.032 Uiso 1 1 calc R . .
C30 C -0.30806(16) 0.71871(14) 0.62927(10) 0.0297(3) Uani 1 1 d . . .
H30 H -0.2311 0.7298 0.5850 0.036 Uiso 1 1 calc R . .
C31 C -0.40606(16) 0.70315(14) 0.60357(9) 0.0295(3) Uani 1 1 d . . .
C32 C -0.51854(16) 0.68617(14) 0.66478(10) 0.0287(3) Uani 1 1 d . . .
H32 H -0.5849 0.6762 0.6446 0.034 Uiso 1 1 calc R . .
C33 C -0.53256(15) 0.68401(13) 0.75711(10) 0.0254(3) Uani 1 1 d . . .
H33 H -0.6089 0.6714 0.8007 0.031 Uiso 1 1 calc R . .
F3 F -0.39261(10) 0.70638(9) 0.51310(6) 0.0427(2) Uani 1 1 d . . .
C34 C 0.15476(16) 0.14517(15) 0.65385(10) 0.0317(3) Uani 1 1 d . . .
C35 C 0.04855(17) 0.11108(15) 0.65778(10) 0.0321(3) Uani 1 1 d . . .
H35 H 0.0720 0.0186 0.6542 0.039 Uiso 1 1 calc R . .
C36 C -0.09060(17) 0.20916(17) 0.66685(10) 0.0375(4) Uani 1 1 d . . .
H36 H -0.1617 0.1837 0.6695 0.045 Uiso 1 1 calc R . .
C37 C -0.12679(17) 0.34431(16) 0.67206(10) 0.0379(4) Uani 1 1 d . . .
H37 H -0.2226 0.4119 0.6787 0.045 Uiso 1 1 calc R . .
C38 C -0.02249(19) 0.37980(16) 0.66755(11) 0.0404(4) Uani 1 1 d . . .
H38 H -0.0463 0.4724 0.6705 0.048 Uiso 1 1 calc R . .
C39 C 0.11640(17) 0.28213(16) 0.65882(10) 0.0365(4) Uani 1 1 d . . .
H39 H 0.1870 0.3084 0.6561 0.044 Uiso 1 1 calc R . .
C40 C 0.30558(18) 0.03924(17) 0.64532(13) 0.0454(4) Uani 1 1 d . . .
H40 H 0.2998 0.0073 0.7049 0.068 Uiso 1 1 calc R . .
H40A H 0.3711 0.0785 0.6290 0.068 Uiso 1 1 calc R . .
H40B H 0.3442 -0.0372 0.5964 0.068 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3816(17) . ?
C1 C6 1.4001(17) . ?
C1 C8 1.5009(18) . ?
C2 C3 1.4006(18) . ?
C2 C9 1.5044(18) . ?
C3 C4 1.3831(18) . ?
C3 C10 1.5010(18) . ?
C4 C5 1.4041(17) . ?
C4 C11 1.5014(18) . ?
C5 C6 1.3783(18) . ?
C5 C12 1.5064(17) . ?
C6 C7 1.5036(17) . ?
C7 O1 1.1973(15) . ?
C7 N1 1.3976(16) . ?
N1 C8 1.3937(17) . ?
N1 C13 1.4634(16) . ?
C8 O2 1.2074(15) . ?
C9 O3 1.2044(15) . ?
C9 N2 1.3952(17) . ?
N2 C10 1.3934(17) . ?
N2 C20 1.4690(17) . ?
C10 O4 1.2077(15) . ?
C11 O5 1.2065(15) . ?
C11 N3 1.3940(17) . ?
N3 C12 1.3927(16) . ?
N3 C27 1.4699(16) . ?
C12 O6 1.2083(15) . ?
C13 C14 1.5108(18) . ?
C13 H13 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.3870(18) . ?
C14 C19 1.3885(18) . ?
C15 C16 1.3903(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.366(2) . ?
C16 H16 0.9500 . ?
C17 F1 1.3560(16) . ?
C17 C18 1.3753(19) . ?
C18 C19 1.3847(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.5089(18) . ?
C20 H20 0.9900 . ?
C20 H20A 0.9900 . ?
C21 C22 1.3897(19) . ?
C21 C26 1.3934(18) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.369(2) . ?
C23 H23 0.9500 . ?
C24 F2 1.3599(16) . ?
C24 C25 1.377(2) . ?
C25 C26 1.3825(19) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.5099(18) . ?
C27 H27 0.9900 . ?
C27 H27A 0.9900 . ?
C28 C33 1.3878(19) . ?
C28 C29 1.3916(19) . ?
C29 C30 1.3858(19) . ?
C29 H29 0.9500 . ?
C30 C31 1.370(2) . ?
C30 H30 0.9500 . ?
C31 F3 1.3635(16) . ?
C31 C32 1.372(2) . ?
C32 C33 1.390(2) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.388(2) . ?
C34 C39 1.397(2) . ?
C34 C40 1.502(2) . ?
C35 C36 1.381(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.383(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.376(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.379(2) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.86(11) . . ?
C2 C1 C8 131.96(11) . . ?
C6 C1 C8 108.13(10) . . ?
C1 C2 C3 120.20(11) . . ?
C1 C2 C9 131.28(11) . . ?
C3 C2 C9 108.36(10) . . ?
C4 C3 C2 119.82(11) . . ?
C4 C3 C10 132.36(11) . . ?
C2 C3 C10 107.66(11) . . ?
C3 C4 C5 119.99(11) . . ?
C3 C4 C11 132.10(11) . . ?
C5 C4 C11 107.75(11) . . ?
C6 C5 C4 119.93(11) . . ?
C6 C5 C12 132.00(11) . . ?
C4 C5 C12 107.95(11) . . ?
C5 C6 C1 120.20(11) . . ?
C5 C6 C7 131.72(11) . . ?
C1 C6 C7 107.95(11) . . ?
O1 C7 N1 125.07(12) . . ?
O1 C7 C6 129.70(12) . . ?
N1 C7 C6 105.23(11) . . ?
C8 N1 C7 113.23(10) . . ?
C8 N1 C13 123.17(10) . . ?
C7 N1 C13 123.57(11) . . ?
O2 C8 N1 124.94(12) . . ?
O2 C8 C1 129.73(12) . . ?
N1 C8 C1 105.32(10) . . ?
O3 C9 N2 125.28(12) . . ?
O3 C9 C2 129.77(12) . . ?
N2 C9 C2 104.94(10) . . ?
C10 N2 C9 113.33(11) . . ?
C10 N2 C20 123.75(11) . . ?
C9 N2 C20 122.86(11) . . ?
O4 C10 N2 124.42(12) . . ?
O4 C10 C3 130.00(12) . . ?
N2 C10 C3 105.57(11) . . ?
O5 C11 N3 124.95(12) . . ?
O5 C11 C4 129.33(12) . . ?
N3 C11 C4 105.72(10) . . ?
C12 N3 C11 113.17(10) . . ?
C12 N3 C27 122.75(11) . . ?
C11 N3 C27 124.03(11) . . ?
O6 C12 N3 125.12(12) . . ?
O6 C12 C5 129.48(12) . . ?
N3 C12 C5 105.40(10) . . ?
N1 C13 C14 112.31(10) . . ?
N1 C13 H13 109.1 . . ?
C14 C13 H13 109.1 . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
H13 C13 H13A 107.9 . . ?
C15 C14 C19 119.32(12) . . ?
C15 C14 C13 121.00(12) . . ?
C19 C14 C13 119.67(12) . . ?
C14 C15 C16 120.63(13) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.09(13) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
F1 C17 C16 118.94(13) . . ?
F1 C17 C18 117.84(13) . . ?
C16 C17 C18 123.22(13) . . ?
C17 C18 C19 118.02(13) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
C18 C19 C14 120.71(12) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
N2 C20 C21 110.67(10) . . ?
N2 C20 H20 109.5 . . ?
C21 C20 H20 109.5 . . ?
N2 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
H20 C20 H20A 108.1 . . ?
C22 C21 C26 118.92(12) . . ?
C22 C21 C20 120.50(12) . . ?
C26 C21 C20 120.56(12) . . ?
C23 C22 C21 120.89(13) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 118.18(13) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
F2 C24 C23 118.84(13) . . ?
F2 C24 C25 118.17(13) . . ?
C23 C24 C25 122.98(13) . . ?
C24 C25 C26 118.18(13) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C25 C26 C21 120.83(13) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N3 C27 C28 111.87(10) . . ?
N3 C27 H27 109.2 . . ?
C28 C27 H27 109.2 . . ?
N3 C27 H27A 109.2 . . ?
C28 C27 H27A 109.2 . . ?
H27 C27 H27A 107.9 . . ?
C33 C28 C29 118.98(13) . . ?
C33 C28 C27 120.42(12) . . ?
C29 C28 C27 120.59(12) . . ?
C30 C29 C28 121.00(13) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 117.98(14) . . ?
C31 C30 H30 121.0 . . ?
C29 C30 H30 121.0 . . ?
F3 C31 C30 118.55(13) . . ?
F3 C31 C32 118.24(13) . . ?
C30 C31 C32 123.20(13) . . ?
C31 C32 C33 118.06(14) . . ?
C31 C32 H32 121.0 . . ?
C33 C32 H32 121.0 . . ?
C28 C33 C32 120.77(13) . . ?
C28 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C35 C34 C39 117.71(14) . . ?
C35 C34 C40 121.48(14) . . ?
C39 C34 C40 120.81(14) . . ?
C36 C35 C34 121.22(15) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C37 120.26(15) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C38 C37 C36 119.29(15) . . ?
C38 C37 H37 120.4 . . ?
C36 C37 H37 120.4 . . ?
C37 C38 C39 120.57(16) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C38 C39 C34 120.94(15) . . ?
C38 C39 H39 119.5 . . ?
C34 C39 H39 119.5 . . ?
C34 C40 H40 109.5 . . ?
C34 C40 H40A 109.5 . . ?
H40 C40 H40A 109.5 . . ?
C34 C40 H40B 109.5 . . ?
H40 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.01(17) . . . . ?
C8 C1 C2 C3 177.08(12) . . . . ?
C6 C1 C2 C9 -174.83(12) . . . . ?
C8 C1 C2 C9 2.2(2) . . . . ?
C1 C2 C3 C4 0.04(17) . . . . ?
C9 C2 C3 C4 175.96(10) . . . . ?
C1 C2 C3 C10 -175.92(10) . . . . ?
C9 C2 C3 C10 0.00(13) . . . . ?
C2 C3 C4 C5 0.01(17) . . . . ?
C10 C3 C4 C5 174.79(11) . . . . ?
C2 C3 C4 C11 -174.67(12) . . . . ?
C10 C3 C4 C11 0.1(2) . . . . ?
C3 C4 C5 C6 -0.11(17) . . . . ?
C11 C4 C5 C6 175.74(10) . . . . ?
C3 C4 C5 C12 -176.51(10) . . . . ?
C11 C4 C5 C12 -0.65(13) . . . . ?
C4 C5 C6 C1 0.17(17) . . . . ?
C12 C5 C6 C1 175.56(12) . . . . ?
C4 C5 C6 C7 -175.12(12) . . . . ?
C12 C5 C6 C7 0.3(2) . . . . ?
C2 C1 C6 C5 -0.12(17) . . . . ?
C8 C1 C6 C5 -177.83(10) . . . . ?
C2 C1 C6 C7 176.19(10) . . . . ?
C8 C1 C6 C7 -1.52(13) . . . . ?
C5 C6 C7 O1 -4.7(2) . . . . ?
C1 C6 C7 O1 179.56(13) . . . . ?
C5 C6 C7 N1 174.79(12) . . . . ?
C1 C6 C7 N1 -0.93(13) . . . . ?
O1 C7 N1 C8 -177.16(12) . . . . ?
C6 C7 N1 C8 3.30(13) . . . . ?
O1 C7 N1 C13 0.64(19) . . . . ?
C6 C7 N1 C13 -178.90(10) . . . . ?
C7 N1 C8 O2 174.46(11) . . . . ?
C13 N1 C8 O2 -3.36(19) . . . . ?
C7 N1 C8 C1 -4.20(13) . . . . ?
C13 N1 C8 C1 177.98(10) . . . . ?
C2 C1 C8 O2 7.5(2) . . . . ?
C6 C1 C8 O2 -175.16(12) . . . . ?
C2 C1 C8 N1 -173.91(12) . . . . ?
C6 C1 C8 N1 3.42(13) . . . . ?
C1 C2 C9 O3 -6.9(2) . . . . ?
C3 C2 C9 O3 177.84(13) . . . . ?
C1 C2 C9 N2 173.14(12) . . . . ?
C3 C2 C9 N2 -2.16(13) . . . . ?
O3 C9 N2 C10 -176.26(12) . . . . ?
C2 C9 N2 C10 3.73(13) . . . . ?
O3 C9 N2 C20 6.56(19) . . . . ?
C2 C9 N2 C20 -173.44(10) . . . . ?
C9 N2 C10 O4 176.65(11) . . . . ?
C20 N2 C10 O4 -6.20(19) . . . . ?
C9 N2 C10 C3 -3.76(13) . . . . ?
C20 N2 C10 C3 173.39(10) . . . . ?
C4 C3 C10 O4 6.5(2) . . . . ?
C2 C3 C10 O4 -178.27(12) . . . . ?
C4 C3 C10 N2 -173.09(12) . . . . ?
C2 C3 C10 N2 2.17(13) . . . . ?
C3 C4 C11 O5 -4.8(2) . . . . ?
C5 C4 C11 O5 -179.97(12) . . . . ?
C3 C4 C11 N3 174.98(12) . . . . ?
C5 C4 C11 N3 -0.18(13) . . . . ?
O5 C11 N3 C12 -179.15(11) . . . . ?
C4 C11 N3 C12 1.05(13) . . . . ?
O5 C11 N3 C27 3.43(19) . . . . ?
C4 C11 N3 C27 -176.37(10) . . . . ?
C11 N3 C12 O6 178.55(11) . . . . ?
C27 N3 C12 O6 -4.00(19) . . . . ?
C11 N3 C12 C5 -1.43(13) . . . . ?
C27 N3 C12 C5 176.02(10) . . . . ?
C6 C5 C12 O6 5.5(2) . . . . ?
C4 C5 C12 O6 -178.73(12) . . . . ?
C6 C5 C12 N3 -174.55(12) . . . . ?
C4 C5 C12 N3 1.25(13) . . . . ?
C8 N1 C13 C14 -84.43(14) . . . . ?
C7 N1 C13 C14 97.99(14) . . . . ?
N1 C13 C14 C15 -65.92(16) . . . . ?
N1 C13 C14 C19 114.59(13) . . . . ?
C19 C14 C15 C16 0.49(19) . . . . ?
C13 C14 C15 C16 -179.00(12) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C15 C16 C17 F1 -179.79(12) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
F1 C17 C18 C19 179.23(12) . . . . ?
C16 C17 C18 C19 0.0(2) . . . . ?
C17 C18 C19 C14 0.9(2) . . . . ?
C15 C14 C19 C18 -1.1(2) . . . . ?
C13 C14 C19 C18 178.42(12) . . . . ?
C10 N2 C20 C21 -83.66(14) . . . . ?
C9 N2 C20 C21 93.22(14) . . . . ?
N2 C20 C21 C22 -80.60(15) . . . . ?
N2 C20 C21 C26 97.77(14) . . . . ?
C26 C21 C22 C23 -0.81(19) . . . . ?
C20 C21 C22 C23 177.59(12) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 F2 179.65(11) . . . . ?
C22 C23 C24 C25 0.8(2) . . . . ?
F2 C24 C25 C26 -179.80(12) . . . . ?
C23 C24 C25 C26 -1.0(2) . . . . ?
C24 C25 C26 C21 0.2(2) . . . . ?
C22 C21 C26 C25 0.66(19) . . . . ?
C20 C21 C26 C25 -177.74(12) . . . . ?
C12 N3 C27 C28 -79.58(14) . . . . ?
C11 N3 C27 C28 97.60(14) . . . . ?
N3 C27 C28 C33 105.91(14) . . . . ?
N3 C27 C28 C29 -73.71(15) . . . . ?
C33 C28 C29 C30 -0.50(19) . . . . ?
C27 C28 C29 C30 179.12(12) . . . . ?
C28 C29 C30 C31 0.8(2) . . . . ?
C29 C30 C31 F3 178.79(12) . . . . ?
C29 C30 C31 C32 -0.4(2) . . . . ?
F3 C31 C32 C33 -179.50(11) . . . . ?
C30 C31 C32 C33 -0.4(2) . . . . ?
C29 C28 C33 C32 -0.24(18) . . . . ?
C27 C28 C33 C32 -179.86(11) . . . . ?
C31 C32 C33 C28 0.66(19) . . . . ?
C39 C34 C35 C36 -0.4(2) . . . . ?
C40 C34 C35 C36 179.15(14) . . . . ?
C34 C35 C36 C37 0.1(2) . . . . ?
C35 C36 C37 C38 0.4(2) . . . . ?
C36 C37 C38 C39 -0.6(2) . . . . ?
C37 C38 C39 C34 0.3(2) . . . . ?
C35 C34 C39 C38 0.1(2) . . . . ?
C40 C34 C39 C38 -179.38(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_F-pyridine
_database_code_depnum_ccdc_archive 'CCDC 1557871'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H18 F3 N3 O6, C5 H5 N'
_chemical_formula_sum            'C38 H23 F3 N4 O6'
_chemical_formula_weight         688.60

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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.1691(8)
_cell_length_b                   11.1691(8)
_cell_length_c                   44.161(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4771.0(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    4030
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      30.3

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2124
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16853
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1929
_reflns_number_gt                1844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0794P)²+5.1963P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1929
_refine_ls_number_parameters     178
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73067(18) 0.25383(17) 0.13650(4) 0.0181(4) Uani 1 1 d . . .
C2 C 0.76805(19) 0.14228(18) 0.13325(4) 0.0205(4) Uani 1 1 d . . .
N1 N 0.64298(16) 0.02004(15) 0.13042(4) 0.0236(4) Uani 1 1 d . . .
C3 C 0.52862(19) 0.03702(18) 0.13319(4) 0.0220(4) Uani 1 1 d . . .
C4 C 0.58594(18) 0.18971(17) 0.13652(4) 0.0188(4) Uani 1 1 d . . .
O1 O 0.88066(14) 0.15153(14) 0.13301(3) 0.0276(4) Uani 1 1 d . . .
O2 O 0.40972(14) -0.05483(13) 0.13266(3) 0.0317(4) Uani 1 1 d . . .
C5 C 0.6331(2) -0.11406(19) 0.12408(4) 0.0284(5) Uani 1 1 d . . .
H5 H 0.5439 -0.1894 0.1318 0.034 Uiso 1 1 calc R . .
H5A H 0.7083 -0.1189 0.1348 0.034 Uiso 1 1 calc R . .
C6 C 0.6434(2) -0.13457(18) 0.09049(5) 0.0285(5) Uani 1 1 d . . .
C7 C 0.7568(3) -0.1375(2) 0.07899(5) 0.0384(5) Uani 1 1 d . . .
H7 H 0.8284 -0.1265 0.0923 0.046 Uiso 1 1 calc R . .
C8 C 0.7682(3) -0.1564(3) 0.04823(5) 0.0479(6) Uani 1 1 d . . .
H8 H 0.8461 -0.1591 0.0404 0.057 Uiso 1 1 calc R . .
C9 C 0.6640(3) -0.1709(2) 0.02947(5) 0.0438(6) Uani 1 1 d . . .
C10 C 0.5502(3) -0.1674(3) 0.03982(5) 0.0469(6) Uani 1 1 d . . .
H10 H 0.4801 -0.1767 0.0263 0.056 Uiso 1 1 calc R . .
C11 C 0.5400(2) -0.1500(2) 0.07063(5) 0.0399(6) Uani 1 1 d . . .
H11 H 0.4612 -0.1486 0.0783 0.048 Uiso 1 1 calc R . .
F1 F 0.67356(19) -0.18995(18) -0.00062(3) 0.0639(5) Uani 1 1 d . . .
N2 N 0.6515(11) 0.4359(11) 0.0558(2) 0.0558(18) Uani 0.33 1 d PGU A -1
C12 C 0.7896(12) 0.4725(11) 0.0530(2) 0.0559(18) Uani 0.33 1 d PGU A -1
H12 H 0.8582 0.5666 0.0500 0.067 Uiso 0.33 1 calc PR A -1
C13 C 0.8275(12) 0.3715(12) 0.0544(3) 0.0569(18) Uani 0.33 1 d PGU A -1
H13 H 0.9219 0.3965 0.0525 0.068 Uiso 0.33 1 calc PR A -1
C14 C 0.7272(12) 0.2339(12) 0.0587(2) 0.0568(18) Uani 0.33 1 d PGU A -1
H14 H 0.7530 0.1648 0.0597 0.068 Uiso 0.33 1 calc PR A -1
C15 C 0.5890(11) 0.1973(11) 0.0616(2) 0.0557(18) Uani 0.33 1 d PGU A -1
H15 H 0.5205 0.1032 0.0645 0.067 Uiso 0.33 1 calc PR A -1
C16 C 0.5512(10) 0.2983(11) 0.0601(2) 0.0556(19) Uani 0.33 1 d PGU A -1
H16 H 0.4568 0.2733 0.0621 0.067 Uiso 0.33 1 calc PR A -1


_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 C4 1.381(2) 2_655 ?
C1 C4 1.403(2) . ?
C1 C2 1.506(2) . ?
C2 O1 1.209(2) . ?
C2 N1 1.387(2) . ?
N1 C3 1.387(2) . ?
N1 C5 1.473(2) . ?
C3 O2 1.206(2) . ?
C3 C4 1.499(2) . ?
C4 C1 1.381(2) 3_665 ?
C5 C6 1.514(3) . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C7 1.381(3) . ?
C6 C11 1.390(3) . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(4) . ?
C8 H8 0.9500 . ?
C9 F1 1.358(3) . ?
C9 C10 1.369(4) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
N2 C12 1.3900 . ?
N2 C16 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 H16 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
C4 C1 C4 120.14(17) 2_655 . ?
C4 C1 C2 131.90(16) 2_655 . ?
C4 C1 C2 107.64(15) . . ?
O1 C2 N1 125.17(16) . . ?
O1 C2 C1 129.55(17) . . ?
N1 C2 C1 105.28(14) . . ?
C2 N1 C3 113.61(14) . . ?
C2 N1 C5 123.01(16) . . ?
C3 N1 C5 123.35(15) . . ?
O2 C3 N1 125.42(16) . . ?
O2 C3 C4 129.18(17) . . ?
N1 C3 C4 105.39(14) . . ?
C1 C4 C1 119.86(17) 3_665 . ?
C1 C4 C3 131.84(16) 3_665 . ?
C1 C4 C3 107.96(15) . . ?
N1 C5 C6 111.55(15) . . ?
N1 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
N1 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
H5 C5 H5A 108.0 . . ?
C7 C6 C11 118.7(2) . . ?
C7 C6 C5 120.25(19) . . ?
C11 C6 C5 121.05(19) . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 118.1(2) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
F1 C9 C10 118.5(2) . . ?
F1 C9 C8 118.8(2) . . ?
C10 C9 C8 122.7(2) . . ?
C9 C10 C11 118.3(2) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C6 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C12 N2 C16 120.0 . . ?
N2 C12 C13 120.0 . . ?
N2 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 N2 120.0 . . ?
C15 C16 H16 120.0 . . ?
N2 C16 H16 120.0 . . ?

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
C4 C1 C2 O1 8.8(3) 2_655 . . . ?
C4 C1 C2 O1 -177.81(18) . . . . ?
C4 C1 C2 N1 -171.24(18) 2_655 . . . ?
C4 C1 C2 N1 2.16(19) . . . . ?
O1 C2 N1 C3 176.41(17) . . . . ?
C1 C2 N1 C3 -3.6(2) . . . . ?
O1 C2 N1 C5 -5.5(3) . . . . ?
C1 C2 N1 C5 174.56(15) . . . . ?
C2 N1 C3 O2 -177.11(18) . . . . ?
C5 N1 C3 O2 4.8(3) . . . . ?
C2 N1 C3 C4 3.5(2) . . . . ?
C5 N1 C3 C4 -174.66(16) . . . . ?
C4 C1 C4 C1 0.1(3) 2_655 . . 3_665 ?
C2 C1 C4 C1 -174.21(12) . . . 3_665 ?
C4 C1 C4 C3 174.14(13) 2_655 . . . ?
C2 C1 C4 C3 -0.18(19) . . . . ?
O2 C3 C4 C1 -8.2(3) . . . 3_665 ?
N1 C3 C4 C1 171.17(18) . . . 3_665 ?
O2 C3 C4 C1 178.72(19) . . . . ?
N1 C3 C4 C1 -1.87(19) . . . . ?
C2 N1 C5 C6 -84.2(2) . . . . ?
C3 N1 C5 C6 93.7(2) . . . . ?
N1 C5 C6 C7 112.4(2) . . . . ?
N1 C5 C6 C11 -67.3(2) . . . . ?
C11 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 179.9(2) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
C7 C8 C9 F1 -179.7(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
F1 C9 C10 C11 179.0(2) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C6 0.8(4) . . . . ?
C7 C6 C11 C10 -0.3(3) . . . . ?
C5 C6 C11 C10 179.4(2) . . . . ?
C16 N2 C12 C13 0.0 . . . . ?
N2 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 N2 0.0 . . . . ?
C12 N2 C16 C15 0.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_H-acetone
_database_code_depnum_ccdc_archive 'CCDC 1557866'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H34 N4 O9'
_chemical_formula_sum            'C47 H34 N4 O9'
_chemical_formula_weight         798.78

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   19.8152(6)
_cell_length_b                   22.7474(7)
_cell_length_c                   25.6460(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     11559.8(6)
_cell_formula_units_Z            12
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    26282
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      30.5

_exptl_crystal_description       block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4992
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            128341
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.50
_reflns_number_total             21458
_reflns_number_gt                18932
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0386P)²+0.7826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(5)
_refine_ls_number_reflns         21458
_refine_ls_number_parameters     1627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.00972(12) 0.78355(11) 0.46648(10) 0.0264(6) Uani 1 1 d . . .
C2 C 0.01330(12) 0.78495(11) 0.52091(10) 0.0241(6) Uani 1 1 d . . .
C3 C -0.02899(12) 0.82148(11) 0.54916(10) 0.0231(5) Uani 1 1 d . . .
C4 C -0.07630(12) 0.85739(11) 0.52326(10) 0.0232(6) Uani 1 1 d . . .
C5 C -0.08061(12) 0.85484(11) 0.46928(10) 0.0222(5) Uani 1 1 d . . .
C6 C -0.03724(12) 0.81858(11) 0.44059(10) 0.0247(6) Uani 1 1 d . . .
C7 C 0.06317(13) 0.74201(11) 0.44674(11) 0.0293(6) Uani 1 1 d . . .
N1 N 0.09430(11) 0.72043(9) 0.49167(9) 0.0316(5) Uani 1 1 d . . .
C8 C 0.06807(13) 0.74350(11) 0.53777(11) 0.0291(6) Uani 1 1 d . . .
O1 O 0.07798(9) 0.72852(9) 0.40248(8) 0.0371(5) Uani 1 1 d . . .
O2 O 0.08690(9) 0.73093(8) 0.58124(8) 0.0340(5) Uani 1 1 d . . .
C9 C 0.15110(14) 0.67817(12) 0.49120(13) 0.0374(7) Uani 1 1 d . . .
H1 H 0.1501 0.6553 0.4584 0.045 Uiso 1 1 calc R . .
H2 H 0.1461 0.6503 0.5206 0.045 Uiso 1 1 calc R . .
C10 C 0.21824(13) 0.70978(11) 0.49573(12) 0.0308(6) Uani 1 1 d . . .
C11 C 0.25289(13) 0.72613(12) 0.45120(11) 0.0315(6) Uani 1 1 d . . .
H3 H 0.2354 0.7159 0.4179 0.038 Uiso 1 1 calc R . .
C12 C 0.31354(13) 0.75756(12) 0.45467(11) 0.0332(7) Uani 1 1 d . . .
H4 H 0.3370 0.7685 0.4239 0.040 Uiso 1 1 calc R . .
C13 C 0.33906(13) 0.77257(11) 0.50296(12) 0.0326(6) Uani 1 1 d . . .
H5 H 0.3798 0.7945 0.5055 0.039 Uiso 1 1 calc R . .
C14 C 0.30512(14) 0.75556(12) 0.54767(11) 0.0339(7) Uani 1 1 d . . .
H6 H 0.3231 0.7654 0.5809 0.041 Uiso 1 1 calc R . .
C15 C 0.24487(14) 0.72424(12) 0.54447(11) 0.0340(7) Uani 1 1 d . . .
H7 H 0.2220 0.7127 0.5754 0.041 Uiso 1 1 calc R . .
C16 C -0.03494(13) 0.83318(11) 0.60678(10) 0.0259(6) Uani 1 1 d . . .
N2 N -0.08512(10) 0.87627(9) 0.61094(8) 0.0241(5) Uani 1 1 d . . .
C17 C -0.11357(12) 0.89230(11) 0.56342(10) 0.0238(6) Uani 1 1 d . . .
O3 O -0.00491(9) 0.81193(8) 0.64284(7) 0.0333(5) Uani 1 1 d . . .
O4 O -0.15854(9) 0.92770(7) 0.55792(7) 0.0285(4) Uani 1 1 d . . .
C18 C -0.10992(14) 0.89903(12) 0.66107(10) 0.0297(6) Uani 1 1 d . . .
H8 H -0.1239 0.9405 0.6569 0.036 Uiso 1 1 calc R . .
H9 H -0.0732 0.8976 0.6872 0.036 Uiso 1 1 calc R . .
C19 C -0.16876(13) 0.86326(12) 0.67996(9) 0.0268(6) Uani 1 1 d . . .
C20 C -0.15780(16) 0.81282(12) 0.70995(10) 0.0369(7) Uani 1 1 d . . .
H10 H -0.1133 0.8032 0.7207 0.044 Uiso 1 1 calc R . .
C21 C -0.2109(2) 0.77666(15) 0.72416(13) 0.0535(9) Uani 1 1 d . . .
H11 H -0.2027 0.7423 0.7442 0.064 Uiso 1 1 calc R . .
C22 C -0.2754(2) 0.79071(17) 0.70910(14) 0.0603(11) Uani 1 1 d . . .
H12 H -0.3119 0.7659 0.7187 0.072 Uiso 1 1 calc R . .
C23 C -0.28752(17) 0.84044(19) 0.68023(14) 0.0579(10) Uani 1 1 d . . .
H13 H -0.3323 0.8501 0.6701 0.070 Uiso 1 1 calc R . .
C24 C -0.23418(14) 0.87671(14) 0.66584(11) 0.0381(7) Uani 1 1 d . . .
H14 H -0.2429 0.9112 0.6460 0.046 Uiso 1 1 calc R . .
C25 C -0.12550(13) 0.88730(11) 0.43152(10) 0.0242(6) Uani 1 1 d . . .
N3 N -0.10540(11) 0.86822(9) 0.38226(8) 0.0274(5) Uani 1 1 d . . .
C26 C -0.05277(13) 0.82710(12) 0.38358(11) 0.0287(6) Uani 1 1 d . . .
O5 O -0.16931(9) 0.92336(8) 0.43961(7) 0.0289(4) Uani 1 1 d . . .
O6 O -0.02683(10) 0.80566(9) 0.34560(7) 0.0369(5) Uani 1 1 d . . .
C27 C -0.13500(14) 0.89134(13) 0.33377(10) 0.0333(7) Uani 1 1 d . . .
H15 H -0.1009 0.8893 0.3056 0.040 Uiso 1 1 calc R . .
H16 H -0.1470 0.9332 0.3389 0.040 Uiso 1 1 calc R . .
C28 C -0.19721(13) 0.85781(12) 0.31716(10) 0.0275(6) Uani 1 1 d . . .
C29 C -0.26094(16) 0.87929(16) 0.32845(13) 0.0490(8) Uani 1 1 d . . .
H17 H -0.2659 0.9150 0.3473 0.059 Uiso 1 1 calc R . .
C30 C -0.31788(16) 0.84833(19) 0.31209(14) 0.0619(11) Uani 1 1 d . . .
H18 H -0.3615 0.8633 0.3198 0.074 Uiso 1 1 calc R . .
C31 C -0.31173(16) 0.79647(16) 0.28495(12) 0.0476(8) Uani 1 1 d . . .
H19 H -0.3509 0.7756 0.2743 0.057 Uiso 1 1 calc R . .
C32 C -0.24910(16) 0.77515(14) 0.27335(12) 0.0449(8) Uani 1 1 d . . .
H20 H -0.2445 0.7397 0.2541 0.054 Uiso 1 1 calc R . .
C33 C -0.19206(14) 0.80553(12) 0.28974(11) 0.0364(7) Uani 1 1 d . . .
H21 H -0.1486 0.7901 0.2820 0.044 Uiso 1 1 calc R . .
C34 C 0.60713(12) 0.95727(10) -0.04960(9) 0.0188(5) Uani 1 1 d . . .
C35 C 0.59838(11) 0.96005(10) 0.00453(9) 0.0192(5) Uani 1 1 d . . .
C36 C 0.64545(12) 0.93384(10) 0.03727(9) 0.0191(5) Uani 1 1 d . . .
C37 C 0.70166(12) 0.90473(10) 0.01569(9) 0.0192(5) Uani 1 1 d . . .
C38 C 0.71020(11) 0.90310(10) -0.03830(9) 0.0187(5) Uani 1 1 d . . .
C39 C 0.66289(12) 0.92979(10) -0.07062(9) 0.0195(5) Uani 1 1 d . . .
C40 C 0.54858(12) 0.98883(10) -0.07452(10) 0.0209(5) Uani 1 1 d . . .
N4 N 0.50963(10) 1.00951(9) -0.03323(8) 0.0217(5) Uani 1 1 d . . .
C41 C 0.53516(12) 0.99417(10) 0.01550(10) 0.0217(5) Uani 1 1 d . . .
O7 O 0.53627(8) 0.99678(8) -0.12019(7) 0.0285(4) Uani 1 1 d . . .
O8 O 0.51042(8) 1.00842(8) 0.05660(7) 0.0284(4) Uani 1 1 d . . .
C42 C 0.44758(12) 1.04401(11) -0.04078(10) 0.0250(6) Uani 1 1 d . . .
H22 H 0.4517 1.0671 -0.0734 0.030 Uiso 1 1 calc R . .
H23 H 0.4428 1.0721 -0.0115 0.030 Uiso 1 1 calc R . .
C43 C 0.38476(12) 1.00647(10) -0.04380(10) 0.0226(6) Uani 1 1 d . . .
C44 C 0.35477(12) 0.99472(11) -0.09190(10) 0.0256(6) Uani 1 1 d . . .
H24 H 0.3752 1.0090 -0.1229 0.031 Uiso 1 1 calc R . .
C45 C 0.29528(13) 0.96235(11) -0.09514(11) 0.0311(6) Uani 1 1 d . . .
H25 H 0.2756 0.9547 -0.1282 0.037 Uiso 1 1 calc R . .
C46 C 0.26492(13) 0.94142(11) -0.05038(12) 0.0343(7) Uani 1 1 d . . .
H26 H 0.2241 0.9196 -0.0525 0.041 Uiso 1 1 calc R . .
C47 C 0.29451(14) 0.95250(11) -0.00176(12) 0.0339(7) Uani 1 1 d . . .
H27 H 0.2738 0.9381 0.0291 0.041 Uiso 1 1 calc R . .
C48 C 0.35429(13) 0.98459(11) 0.00138(11) 0.0279(6) Uani 1 1 d . . .
H28 H 0.3744 0.9916 0.0344 0.034 Uiso 1 1 calc R . .
C49 C 0.64955(12) 0.92725(10) 0.09571(9) 0.0211(5) Uani 1 1 d . . .
N5 N 0.70675(10) 0.89347(9) 0.10501(7) 0.0221(5) Uani 1 1 d . . .
C50 C 0.74198(12) 0.87906(10) 0.05971(9) 0.0205(5) Uani 1 1 d . . .
O9 O 0.61241(9) 0.94642(8) 0.12904(6) 0.0266(4) Uani 1 1 d . . .
O10 O 0.79381(8) 0.85067(8) 0.05846(7) 0.0275(4) Uani 1 1 d . . .
C51 C 0.72902(13) 0.87345(12) 0.15668(10) 0.0275(6) Uani 1 1 d . . .
H29 H 0.7450 0.8323 0.1541 0.033 Uiso 1 1 calc R . .
H30 H 0.6902 0.8742 0.1810 0.033 Uiso 1 1 calc R . .
C52 C 0.78480(13) 0.91123(11) 0.17832(9) 0.0253(6) Uani 1 1 d . . .
C53 C 0.77085(15) 0.96551(12) 0.20100(10) 0.0343(7) Uani 1 1 d . . .
H31 H 0.7255 0.9787 0.2032 0.041 Uiso 1 1 calc R . .
C54 C 0.82234(16) 1.00063(13) 0.22042(11) 0.0406(7) Uani 1 1 d . . .
H32 H 0.8122 1.0377 0.2356 0.049 Uiso 1 1 calc R . .
C55 C 0.88859(16) 0.98136(14) 0.21760(11) 0.0409(8) Uani 1 1 d . . .
H33 H 0.9239 1.0051 0.2312 0.049 Uiso 1 1 calc R . .
C56 C 0.90347(14) 0.92790(14) 0.19521(11) 0.0374(7) Uani 1 1 d . . .
H34 H 0.9490 0.9150 0.1929 0.045 Uiso 1 1 calc R . .
C57 C 0.85165(13) 0.89272(13) 0.17591(10) 0.0322(6) Uani 1 1 d . . .
H35 H 0.8621 0.8556 0.1609 0.039 Uiso 1 1 calc R . .
C58 C 0.76298(12) 0.87421(10) -0.07192(9) 0.0211(5) Uani 1 1 d . . .
N6 N 0.74411(10) 0.88771(9) -0.12288(7) 0.0215(5) Uani 1 1 d . . .
C59 C 0.68516(12) 0.92090(11) -0.12608(10) 0.0215(5) Uani 1 1 d . . .
O11 O 0.81099(8) 0.84456(7) -0.06009(7) 0.0248(4) Uani 1 1 d . . .
O12 O 0.65923(9) 0.93778(8) -0.16616(6) 0.0290(4) Uani 1 1 d . . .
C60 C 0.78293(12) 0.86780(11) -0.16865(10) 0.0256(6) Uani 1 1 d . . .
H36 H 0.7545 0.8711 -0.2003 0.031 Uiso 1 1 calc R . .
H37 H 0.7954 0.8260 -0.1642 0.031 Uiso 1 1 calc R . .
C61 C 0.84623(13) 0.90425(12) -0.17564(10) 0.0272(6) Uani 1 1 d . . .
C62 C 0.90876(14) 0.88134(14) -0.16110(12) 0.0391(7) Uani 1 1 d . . .
H38 H 0.9118 0.8422 -0.1483 0.047 Uiso 1 1 calc R . .
C63 C 0.96657(16) 0.91542(18) -0.16529(13) 0.0537(10) Uani 1 1 d . . .
H39 H 1.0088 0.9000 -0.1544 0.064 Uiso 1 1 calc R . .
C64 C 0.96278(18) 0.97101(19) -0.18509(14) 0.0598(10) Uani 1 1 d . . .
H40 H 1.0024 0.9942 -0.1882 0.072 Uiso 1 1 calc R . .
C65 C 0.9009(2) 0.99368(17) -0.20072(15) 0.0684(11) Uani 1 1 d . . .
H41 H 0.8984 1.0323 -0.2148 0.082 Uiso 1 1 calc R . .
C66 C 0.84259(16) 0.96002(14) -0.19589(12) 0.0470(8) Uani 1 1 d . . .
H42 H 0.8003 0.9756 -0.2066 0.056 Uiso 1 1 calc R . .
C67 C 0.78928(12) 0.71497(10) -0.05168(10) 0.0223(5) Uani 1 1 d . . .
C68 C 0.77998(12) 0.71566(10) 0.00232(10) 0.0212(5) Uani 1 1 d . . .
C69 C 0.82962(12) 0.69356(11) 0.03510(10) 0.0225(5) Uani 1 1 d . . .
C70 C 0.89013(12) 0.67153(10) 0.01381(10) 0.0226(6) Uani 1 1 d . . .
C71 C 0.90067(12) 0.67377(10) -0.03955(10) 0.0219(5) Uani 1 1 d . . .
C72 C 0.85019(12) 0.69563(11) -0.07269(10) 0.0241(6) Uani 1 1 d . . .
C73 C 0.72580(12) 0.73804(11) -0.07674(10) 0.0239(6) Uani 1 1 d . . .
N7 N 0.68304(10) 0.75282(9) -0.03515(8) 0.0225(5) Uani 1 1 d . . .
C74 C 0.71235(12) 0.74245(11) 0.01347(10) 0.0234(6) Uani 1 1 d . . .
O13 O 0.71213(9) 0.74459(8) -0.12235(7) 0.0289(4) Uani 1 1 d . . .
O14 O 0.68749(8) 0.75567(8) 0.05488(7) 0.0285(4) Uani 1 1 d . . .
C75 C 0.61674(12) 0.78130(11) -0.04137(11) 0.0259(6) Uani 1 1 d . . .
H43 H 0.6138 0.7975 -0.0771 0.031 Uiso 1 1 calc R . .
H44 H 0.6141 0.8148 -0.0168 0.031 Uiso 1 1 calc R . .
C76 C 0.55584(12) 0.74167(10) -0.03225(10) 0.0210(5) Uani 1 1 d . . .
C77 C 0.51481(12) 0.72621(11) -0.07376(10) 0.0258(6) Uani 1 1 d . . .
H45 H 0.5272 0.7368 -0.1083 0.031 Uiso 1 1 calc R . .
C78 C 0.45523(13) 0.69501(11) -0.06477(11) 0.0296(6) Uani 1 1 d . . .
H46 H 0.4271 0.6846 -0.0933 0.035 Uiso 1 1 calc R . .
C79 C 0.43690(13) 0.67915(11) -0.01484(11) 0.0302(6) Uani 1 1 d . . .
H47 H 0.3960 0.6584 -0.0089 0.036 Uiso 1 1 calc R . .
C80 C 0.47850(13) 0.69372(11) 0.02642(11) 0.0286(6) Uani 1 1 d . . .
H48 H 0.4665 0.6823 0.0608 0.034 Uiso 1 1 calc R . .
C81 C 0.53769(12) 0.72491(11) 0.01810(10) 0.0268(6) Uani 1 1 d . . .
H49 H 0.5659 0.7349 0.0467 0.032 Uiso 1 1 calc R . .
C82 C 0.83188(13) 0.68434(11) 0.09289(10) 0.0247(6) Uani 1 1 d . . .
N8 N 0.89310(10) 0.65566(9) 0.10232(8) 0.0245(5) Uani 1 1 d . . .
C83 C 0.93134(12) 0.64660(10) 0.05774(10) 0.0227(5) Uani 1 1 d . . .
O15 O 0.79121(9) 0.69725(9) 0.12609(7) 0.0343(5) Uani 1 1 d . . .
O16 O 0.98584(8) 0.62248(7) 0.05665(7) 0.0279(4) Uani 1 1 d . . .
C84 C 0.91370(13) 0.63374(12) 0.15365(10) 0.0286(6) Uani 1 1 d . . .
H50 H 0.9345 0.5944 0.1496 0.034 Uiso 1 1 calc R . .
H51 H 0.8733 0.6294 0.1760 0.034 Uiso 1 1 calc R . .
C85 C 0.96346(13) 0.67450(11) 0.17998(10) 0.0253(6) Uani 1 1 d . . .
C86 C 0.94326(14) 0.73032(12) 0.19679(10) 0.0305(6) Uani 1 1 d . . .
H52 H 0.8978 0.7425 0.1921 0.037 Uiso 1 1 calc R . .
C87 C 0.98937(15) 0.76807(12) 0.22032(10) 0.0327(6) Uani 1 1 d . . .
H53 H 0.9756 0.8060 0.2316 0.039 Uiso 1 1 calc R . .
C88 C 1.05544(15) 0.75005(12) 0.22716(11) 0.0368(7) Uani 1 1 d . . .
H54 H 1.0869 0.7756 0.2435 0.044 Uiso 1 1 calc R . .
C89 C 1.07612(14) 0.69501(13) 0.21038(11) 0.0371(7) Uani 1 1 d . . .
H55 H 1.1217 0.6831 0.2150 0.045 Uiso 1 1 calc R . .
C90 C 1.03004(14) 0.65721(12) 0.18672(10) 0.0321(6) Uani 1 1 d . . .
H56 H 1.0442 0.6195 0.1752 0.038 Uiso 1 1 calc R . .
C91 C 0.96054(12) 0.65716(11) -0.07207(10) 0.0250(6) Uani 1 1 d . . .
N9 N 0.94221(11) 0.67082(9) -0.12333(8) 0.0270(5) Uani 1 1 d . . .
C92 C 0.87678(13) 0.69414(11) -0.12731(10) 0.0264(6) Uani 1 1 d . . .
O17 O 1.01461(9) 0.63706(8) -0.05915(7) 0.0309(4) Uani 1 1 d . . .
O18 O 0.85046(9) 0.70931(9) -0.16780(7) 0.0375(5) Uani 1 1 d . . .
C93 C 0.98709(13) 0.66225(12) -0.16847(10) 0.0311(6) Uani 1 1 d . . .
H57 H 0.9594 0.6522 -0.1994 0.037 Uiso 1 1 calc R . .
H58 H 1.0174 0.6286 -0.1614 0.037 Uiso 1 1 calc R . .
C94 C 1.02940(13) 0.71584(11) -0.18079(10) 0.0265(6) Uani 1 1 d . . .
C95 C 1.08754(13) 0.72802(12) -0.15246(10) 0.0289(6) Uani 1 1 d . . .
H59 H 1.1013 0.7021 -0.1254 0.035 Uiso 1 1 calc R . .
C96 C 1.12561(14) 0.77751(13) -0.16331(11) 0.0352(7) Uani 1 1 d . . .
H60 H 1.1651 0.7855 -0.1436 0.042 Uiso 1 1 calc R . .
C97 C 1.10626(15) 0.81549(14) -0.20299(11) 0.0393(7) Uani 1 1 d . . .
H61 H 1.1323 0.8496 -0.2104 0.047 Uiso 1 1 calc R . .
C98 C 1.04856(15) 0.80332(14) -0.23180(11) 0.0387(7) Uani 1 1 d . . .
H62 H 1.0353 0.8289 -0.2592 0.046 Uiso 1 1 calc R . .
C99 C 1.01050(14) 0.75408(12) -0.22057(10) 0.0327(7) Uani 1 1 d . . .
H63 H 0.9709 0.7462 -0.2403 0.039 Uiso 1 1 calc R . .
C100 C 0.65356(13) 0.44785(11) -0.03106(11) 0.0296(6) Uani 1 1 d . . .
C101 C 0.64816(13) 0.44937(11) 0.02316(11) 0.0280(6) Uani 1 1 d . . .
C102 C 0.69559(13) 0.42094(11) 0.05401(11) 0.0275(6) Uani 1 1 d . . .
C103 C 0.75213(12) 0.39512(11) 0.03063(10) 0.0229(5) Uani 1 1 d . . .
C104 C 0.75858(12) 0.39519(10) -0.02302(10) 0.0219(5) Uani 1 1 d . . .
C105 C 0.70776(12) 0.41963(11) -0.05428(10) 0.0252(6) Uani 1 1 d . . .
C106 C 0.59619(13) 0.48324(12) -0.05313(13) 0.0340(7) Uani 1 1 d . . .
N10 N 0.56083(11) 0.50498(10) -0.01020(11) 0.0387(6) Uani 1 1 d . . .
C107 C 0.59005(14) 0.48861(13) 0.03728(13) 0.0385(7) Uani 1 1 d . . .
O19 O 0.58239(9) 0.49356(9) -0.09827(9) 0.0429(5) Uani 1 1 d . . .
O20 O 0.57217(10) 0.50598(9) 0.07993(9) 0.0503(6) Uani 1 1 d . . .
C108 C 0.50762(14) 0.55009(13) -0.01392(15) 0.0486(9) Uani 1 1 d . . .
H64 H 0.5137 0.5724 -0.0467 0.058 Uiso 1 1 calc R . .
H65 H 0.5127 0.5780 0.0154 0.058 Uiso 1 1 calc R . .
C109 C 0.43723(13) 0.52482(11) -0.01275(12) 0.0317(6) Uani 1 1 d . . .
C110 C 0.40411(16) 0.50938(13) -0.05805(12) 0.0406(7) Uani 1 1 d . . .
H66 H 0.4257 0.5150 -0.0907 0.049 Uiso 1 1 calc R . .
C111 C 0.33966(16) 0.48568(14) -0.05639(14) 0.0475(9) Uani 1 1 d . . .
H67 H 0.3176 0.4753 -0.0880 0.057 Uiso 1 1 calc R . .
C112 C 0.30723(15) 0.47701(12) -0.00959(14) 0.0442(8) Uani 1 1 d . . .
H68 H 0.2635 0.4600 -0.0086 0.053 Uiso 1 1 calc R . .
C113 C 0.33925(15) 0.49340(13) 0.03565(12) 0.0409(7) Uani 1 1 d . . .
H69 H 0.3172 0.4881 0.0682 0.049 Uiso 1 1 calc R . .
C114 C 0.40341(14) 0.51763(12) 0.03418(11) 0.0342(7) Uani 1 1 d . . .
H70 H 0.4245 0.5295 0.0657 0.041 Uiso 1 1 calc R . .
C115 C 0.70050(14) 0.41153(12) 0.11174(11) 0.0324(6) Uani 1 1 d . . .
N11 N 0.76045(11) 0.38016(10) 0.11933(8) 0.0302(5) Uani 1 1 d . . .
C116 C 0.79607(13) 0.37007(11) 0.07293(10) 0.0269(6) Uani 1 1 d . . .
O21 O 0.66233(10) 0.42539(9) 0.14628(8) 0.0438(5) Uani 1 1 d . . .
O22 O 0.85064(9) 0.34685(8) 0.07038(7) 0.0294(4) Uani 1 1 d . . .
C117 C 0.78506(16) 0.36055(13) 0.17030(11) 0.0389(7) Uani 1 1 d . . .
H71 H 0.8088 0.3225 0.1662 0.047 Uiso 1 1 calc R . .
H72 H 0.7461 0.3541 0.1938 0.047 Uiso 1 1 calc R . .
C118 C 0.83252(14) 0.40470(12) 0.19488(10) 0.0298(6) Uani 1 1 d . . .
C119 C 0.80706(14) 0.45450(13) 0.21975(10) 0.0333(7) Uani 1 1 d . . .
H73 H 0.7596 0.4599 0.2225 0.040 Uiso 1 1 calc R . .
C120 C 0.85060(14) 0.49645(13) 0.24060(10) 0.0350(7) Uani 1 1 d . . .
H74 H 0.8328 0.5301 0.2578 0.042 Uiso 1 1 calc R . .
C121 C 0.91978(14) 0.48920(14) 0.23633(11) 0.0362(7) Uani 1 1 d . . .
H75 H 0.9495 0.5181 0.2501 0.043 Uiso 1 1 calc R . .
C122 C 0.94540(14) 0.43976(14) 0.21202(11) 0.0387(7) Uani 1 1 d . . .
H76 H 0.9928 0.4348 0.2091 0.046 Uiso 1 1 calc R . .
C123 C 0.90188(14) 0.39705(13) 0.19177(10) 0.0349(7) Uani 1 1 d . . .
H77 H 0.9198 0.3627 0.1759 0.042 Uiso 1 1 calc R . .
C124 C 0.81372(12) 0.37400(11) -0.05803(10) 0.0241(6) Uani 1 1 d . . .
N12 N 0.79011(10) 0.38169(9) -0.10856(8) 0.0263(5) Uani 1 1 d . . .
C125 C 0.72762(13) 0.41027(11) -0.11017(11) 0.0285(6) Uani 1 1 d . . .
O23 O 0.86933(9) 0.35598(8) -0.04653(7) 0.0293(4) Uani 1 1 d . . .
O24 O 0.69864(9) 0.42405(9) -0.15013(7) 0.0371(5) Uani 1 1 d . . .
C126 C 0.82995(14) 0.36775(12) -0.15533(10) 0.0311(6) Uani 1 1 d . . .
H78 H 0.8001 0.3498 -0.1819 0.037 Uiso 1 1 calc R . .
H79 H 0.8652 0.3387 -0.1462 0.037 Uiso 1 1 calc R . .
C127 C 0.86307(12) 0.42218(11) -0.17793(10) 0.0254(6) Uani 1 1 d . . .
C128 C 0.91665(13) 0.44875(12) -0.15094(10) 0.0308(6) Uani 1 1 d . . .
H80 H 0.9315 0.4328 -0.1187 0.037 Uiso 1 1 calc R . .
C129 C 0.94812(15) 0.49845(12) -0.17137(11) 0.0364(7) Uani 1 1 d . . .
H81 H 0.9844 0.5164 -0.1531 0.044 Uiso 1 1 calc R . .
C130 C 0.92649(15) 0.52143(13) -0.21803(11) 0.0378(7) Uani 1 1 d . . .
H82 H 0.9482 0.5552 -0.2318 0.045 Uiso 1 1 calc R . .
C131 C 0.87352(14) 0.49616(13) -0.24527(11) 0.0357(7) Uani 1 1 d . . .
H83 H 0.8592 0.5122 -0.2776 0.043 Uiso 1 1 calc R . .
C132 C 0.84143(13) 0.44667(13) -0.22442(10) 0.0314(6) Uani 1 1 d . . .
H84 H 0.8043 0.4297 -0.2424 0.038 Uiso 1 1 calc R . .
C133 C 0.52607(19) 0.33853(15) 0.16517(13) 0.0543(9) Uani 1 1 d . . .
H85 H 0.4916 0.3086 0.1719 0.081 Uiso 1 1 calc R . .
H86 H 0.5171 0.3732 0.1868 0.081 Uiso 1 1 calc R . .
H87 H 0.5707 0.3226 0.1737 0.081 Uiso 1 1 calc R . .
C134 C 0.52430(15) 0.35550(13) 0.10930(12) 0.0388(7) Uani 1 1 d . . .
C135 C 0.46881(17) 0.39701(14) 0.09273(14) 0.0539(9) Uani 1 1 d . . .
H88 H 0.4770 0.4359 0.1079 0.081 Uiso 1 1 calc R . .
H89 H 0.4252 0.3820 0.1050 0.081 Uiso 1 1 calc R . .
H90 H 0.4682 0.4001 0.0546 0.081 Uiso 1 1 calc R . .
O25 O 0.56454(11) 0.33703(11) 0.07808(9) 0.0569(6) Uani 1 1 d . . .
C136 C 0.24180(17) 0.91913(15) 0.14652(12) 0.0500(9) Uani 1 1 d . . .
H91 H 0.2784 0.9248 0.1213 0.075 Uiso 1 1 calc R . .
H92 H 0.2560 0.8907 0.1730 0.075 Uiso 1 1 calc R . .
H93 H 0.2311 0.9567 0.1633 0.075 Uiso 1 1 calc R . .
C137 C 0.18068(15) 0.89651(12) 0.11897(12) 0.0367(7) Uani 1 1 d . . .
C138 C 0.12148(16) 0.88083(15) 0.15211(12) 0.0487(8) Uani 1 1 d . . .
H94 H 0.0838 0.8687 0.1298 0.073 Uiso 1 1 calc R . .
H95 H 0.1080 0.9150 0.1729 0.073 Uiso 1 1 calc R . .
H96 H 0.1337 0.8484 0.1754 0.073 Uiso 1 1 calc R . .
O26 O 0.17985(11) 0.89044(9) 0.07181(8) 0.0443(5) Uani 1 1 d . . .
C139 C 0.08072(19) 0.16658(16) 0.17626(15) 0.0622(10) Uani 1 1 d . . .
H97 H 0.1246 0.1825 0.1657 0.093 Uiso 1 1 calc R . .
H98 H 0.0875 0.1346 0.2013 0.093 Uiso 1 1 calc R . .
H99 H 0.0538 0.1977 0.1925 0.093 Uiso 1 1 calc R . .
C140 C 0.04500(17) 0.14399(13) 0.13008(13) 0.0448(8) Uani 1 1 d . . .
C141 C -0.01687(17) 0.10797(15) 0.14097(15) 0.0590(10) Uani 1 1 d . . .
H100 H -0.0430 0.1034 0.1088 0.088 Uiso 1 1 calc R . .
H101 H -0.0445 0.1278 0.1673 0.088 Uiso 1 1 calc R . .
H102 H -0.0035 0.0692 0.1539 0.088 Uiso 1 1 calc R . .
O27 O 0.06523(12) 0.15378(10) 0.08580(9) 0.0612(7) 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 C6 1.394(4) . ?
C1 C2 1.398(4) . ?
C1 C7 1.507(4) . ?
C2 C3 1.385(3) . ?
C2 C8 1.501(4) . ?
C3 C4 1.410(3) . ?
C3 C16 1.506(4) . ?
C4 C5 1.388(3) . ?
C4 C17 1.496(3) . ?
C5 C6 1.400(4) . ?
C5 C25 1.508(3) . ?
C6 C26 1.506(4) . ?
C7 O1 1.212(3) . ?
C7 N1 1.396(4) . ?
N1 C8 1.394(3) . ?
N1 C9 1.480(3) . ?
C8 O2 1.210(3) . ?
C9 C10 1.517(4) . ?
C9 H1 0.9900 . ?
C9 H2 0.9900 . ?
C10 C11 1.384(4) . ?
C10 C15 1.396(4) . ?
C11 C12 1.401(4) . ?
C11 H3 0.9500 . ?
C12 C13 1.381(4) . ?
C12 H4 0.9500 . ?
C13 C14 1.384(4) . ?
C13 H5 0.9500 . ?
C14 C15 1.393(4) . ?
C14 H6 0.9500 . ?
C15 H7 0.9500 . ?
C16 O3 1.201(3) . ?
C16 N2 1.400(3) . ?
N2 C17 1.391(3) . ?
N2 C18 1.471(3) . ?
C17 O4 1.209(3) . ?
C18 C19 1.502(4) . ?
C18 H8 0.9900 . ?
C18 H9 0.9900 . ?
C19 C24 1.380(4) . ?
C19 C20 1.398(4) . ?
C20 C21 1.384(4) . ?
C20 H10 0.9500 . ?
C21 C22 1.374(5) . ?
C21 H11 0.9500 . ?
C22 C23 1.373(5) . ?
C22 H12 0.9500 . ?
C23 C24 1.391(5) . ?
C23 H13 0.9500 . ?
C24 H14 0.9500 . ?
C25 O5 1.212(3) . ?
C25 N3 1.394(3) . ?
N3 C26 1.401(3) . ?
N3 C27 1.472(3) . ?
C26 O6 1.205(3) . ?
C27 C28 1.511(4) . ?
C27 H15 0.9900 . ?
C27 H16 0.9900 . ?
C28 C29 1.385(4) . ?
C28 C33 1.385(4) . ?
C29 C30 1.395(5) . ?
C29 H17 0.9500 . ?
C30 C31 1.375(5) . ?
C30 H18 0.9500 . ?
C31 C32 1.365(4) . ?
C31 H19 0.9500 . ?
C32 C33 1.390(4) . ?
C32 H20 0.9500 . ?
C33 H21 0.9500 . ?
C34 C39 1.379(3) . ?
C34 C35 1.400(3) . ?
C34 C40 1.507(3) . ?
C35 C36 1.389(3) . ?
C35 C41 1.500(3) . ?
C36 C37 1.409(3) . ?
C36 C49 1.509(3) . ?
C37 C38 1.396(3) . ?
C37 C50 1.501(3) . ?
C38 C39 1.391(3) . ?
C38 C58 1.506(3) . ?
C39 C59 1.503(3) . ?
C40 O7 1.210(3) . ?
C40 N4 1.392(3) . ?
N4 C41 1.393(3) . ?
N4 C42 1.471(3) . ?
C41 O8 1.207(3) . ?
C42 C43 1.512(3) . ?
C42 H22 0.9900 . ?
C42 H23 0.9900 . ?
C43 C44 1.395(4) . ?
C43 C48 1.398(3) . ?
C44 C45 1.392(4) . ?
C44 H24 0.9500 . ?
C45 C46 1.381(4) . ?
C45 H25 0.9500 . ?
C46 C47 1.401(4) . ?
C46 H26 0.9500 . ?
C47 C48 1.394(4) . ?
C47 H27 0.9500 . ?
C48 H28 0.9500 . ?
C49 O9 1.209(3) . ?
C49 N5 1.390(3) . ?
N5 C50 1.394(3) . ?
N5 C51 1.469(3) . ?
C50 O10 1.214(3) . ?
C51 C52 1.506(4) . ?
C51 H29 0.9900 . ?
C51 H30 0.9900 . ?
C52 C57 1.391(4) . ?
C52 C53 1.393(4) . ?
C53 C54 1.388(4) . ?
C53 H31 0.9500 . ?
C54 C55 1.386(4) . ?
C54 H32 0.9500 . ?
C55 C56 1.377(4) . ?
C55 H33 0.9500 . ?
C56 C57 1.393(4) . ?
C56 H34 0.9500 . ?
C57 H35 0.9500 . ?
C58 O11 1.205(3) . ?
C58 N6 1.394(3) . ?
N6 C59 1.393(3) . ?
N6 C60 1.475(3) . ?
C59 O12 1.212(3) . ?
C60 C61 1.514(3) . ?
C60 H36 0.9900 . ?
C60 H37 0.9900 . ?
C61 C66 1.373(4) . ?
C61 C62 1.395(4) . ?
C62 C63 1.387(4) . ?
C62 H38 0.9500 . ?
C63 C64 1.365(5) . ?
C63 H39 0.9500 . ?
C64 C65 1.389(5) . ?
C64 H40 0.9500 . ?
C65 C66 1.392(4) . ?
C65 H41 0.9500 . ?
C66 H42 0.9500 . ?
C67 C72 1.393(3) . ?
C67 C68 1.397(4) . ?
C67 C73 1.507(3) . ?
C68 C69 1.388(3) . ?
C68 C74 1.500(3) . ?
C69 C70 1.410(3) . ?
C69 C82 1.498(4) . ?
C70 C71 1.385(3) . ?
C70 C83 1.503(3) . ?
C71 C72 1.404(3) . ?
C71 C91 1.498(3) . ?
C72 C92 1.497(4) . ?
C73 O13 1.210(3) . ?
C73 N7 1.403(3) . ?
N7 C74 1.396(3) . ?
N7 C75 1.474(3) . ?
C74 O14 1.209(3) . ?
C75 C76 1.524(3) . ?
C75 H43 0.9900 . ?
C75 H44 0.9900 . ?
C76 C77 1.385(3) . ?
C76 C81 1.394(3) . ?
C77 C78 1.397(3) . ?
C77 H45 0.9500 . ?
C78 C79 1.379(4) . ?
C78 H46 0.9500 . ?
C79 C80 1.382(4) . ?
C79 H47 0.9500 . ?
C80 C81 1.387(4) . ?
C80 H48 0.9500 . ?
C81 H49 0.9500 . ?
C82 O15 1.208(3) . ?
C82 N8 1.398(3) . ?
N8 C83 1.387(3) . ?
N8 C84 1.466(3) . ?
C83 O16 1.211(3) . ?
C84 C85 1.513(4) . ?
C84 H50 0.9900 . ?
C84 H51 0.9900 . ?
C85 C90 1.387(4) . ?
C85 C86 1.399(4) . ?
C86 C87 1.392(4) . ?
C86 H52 0.9500 . ?
C87 C88 1.383(4) . ?
C87 H53 0.9500 . ?
C88 C89 1.386(4) . ?
C88 H54 0.9500 . ?
C89 C90 1.393(4) . ?
C89 H55 0.9500 . ?
C90 H56 0.9500 . ?
C91 O17 1.211(3) . ?
C91 N9 1.399(3) . ?
N9 C92 1.404(3) . ?
N9 C93 1.473(3) . ?
C92 O18 1.212(3) . ?
C93 C94 1.513(4) . ?
C93 H57 0.9900 . ?
C93 H58 0.9900 . ?
C94 C95 1.390(4) . ?
C94 C99 1.392(4) . ?
C95 C96 1.383(4) . ?
C95 H59 0.9500 . ?
C96 C97 1.389(4) . ?
C96 H60 0.9500 . ?
C97 C98 1.389(4) . ?
C97 H61 0.9500 . ?
C98 C99 1.381(4) . ?
C98 H62 0.9500 . ?
C99 H63 0.9500 . ?
C100 C105 1.386(4) . ?
C100 C101 1.395(4) . ?
C100 C106 1.504(4) . ?
C101 C102 1.388(4) . ?
C101 C107 1.501(4) . ?
C102 C103 1.400(3) . ?
C102 C115 1.499(4) . ?
C103 C104 1.382(3) . ?
C103 C116 1.503(4) . ?
C104 C105 1.402(3) . ?
C104 C124 1.494(3) . ?
C105 C125 1.502(4) . ?
C106 O19 1.212(3) . ?
C106 N10 1.396(4) . ?
N10 C107 1.399(4) . ?
N10 C108 1.474(3) . ?
C107 O20 1.216(4) . ?
C108 C109 1.509(4) . ?
C108 H64 0.9900 . ?
C108 H65 0.9900 . ?
C109 C110 1.380(4) . ?
C109 C114 1.387(4) . ?
C110 C111 1.387(4) . ?
C110 H66 0.9500 . ?
C111 C112 1.376(5) . ?
C111 H67 0.9500 . ?
C112 C113 1.374(4) . ?
C112 H68 0.9500 . ?
C113 C114 1.386(4) . ?
C113 H69 0.9500 . ?
C114 H70 0.9500 . ?
C115 O21 1.207(3) . ?
C115 N11 1.399(4) . ?
N11 C116 1.402(3) . ?
N11 C117 1.465(4) . ?
C116 O22 1.205(3) . ?
C117 C118 1.514(4) . ?
C117 H71 0.9900 . ?
C117 H72 0.9900 . ?
C118 C123 1.388(4) . ?
C118 C119 1.394(4) . ?
C119 C120 1.393(4) . ?
C119 H73 0.9500 . ?
C120 C121 1.385(4) . ?
C120 H74 0.9500 . ?
C121 C122 1.383(4) . ?
C121 H75 0.9500 . ?
C122 C123 1.399(4) . ?
C122 H76 0.9500 . ?
C123 H77 0.9500 . ?
C124 O23 1.212(3) . ?
C124 N12 1.389(3) . ?
N12 C125 1.399(3) . ?
N12 C126 1.471(3) . ?
C125 O24 1.216(3) . ?
C126 C127 1.517(4) . ?
C126 H78 0.9900 . ?
C126 H79 0.9900 . ?
C127 C132 1.384(4) . ?
C127 C128 1.404(4) . ?
C128 C129 1.393(4) . ?
C128 H80 0.9500 . ?
C129 C130 1.374(4) . ?
C129 H81 0.9500 . ?
C130 C131 1.386(4) . ?
C130 H82 0.9500 . ?
C131 C132 1.399(4) . ?
C131 H83 0.9500 . ?
C132 H84 0.9500 . ?
C133 C134 1.484(4) . ?
C133 H85 0.9800 . ?
C133 H86 0.9800 . ?
C133 H87 0.9800 . ?
C134 O25 1.206(3) . ?
C134 C135 1.510(4) . ?
C135 H88 0.9800 . ?
C135 H89 0.9800 . ?
C135 H90 0.9800 . ?
C136 C137 1.493(4) . ?
C136 H91 0.9800 . ?
C136 H92 0.9800 . ?
C136 H93 0.9800 . ?
C137 O26 1.217(3) . ?
C137 C138 1.492(4) . ?
C138 H94 0.9800 . ?
C138 H95 0.9800 . ?
C138 H96 0.9800 . ?
C139 C140 1.472(5) . ?
C139 H97 0.9800 . ?
C139 H98 0.9800 . ?
C139 H99 0.9800 . ?
C140 O27 1.225(4) . ?
C140 C141 1.501(4) . ?
C141 H100 0.9800 . ?
C141 H101 0.9800 . ?
C141 H102 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.8(2) . . ?
C6 C1 C7 131.9(2) . . ?
C2 C1 C7 108.3(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 C8 131.6(2) . . ?
C1 C2 C8 108.1(2) . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 C16 131.8(2) . . ?
C4 C3 C16 107.9(2) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 C17 132.7(2) . . ?
C3 C4 C17 108.2(2) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 C25 131.0(2) . . ?
C6 C5 C25 108.2(2) . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 C26 132.2(2) . . ?
C5 C6 C26 108.0(2) . . ?
O1 C7 N1 125.2(3) . . ?
O1 C7 C1 130.1(3) . . ?
N1 C7 C1 104.7(2) . . ?
C8 N1 C7 113.8(2) . . ?
C8 N1 C9 122.3(2) . . ?
C7 N1 C9 123.9(2) . . ?
O2 C8 N1 125.3(2) . . ?
O2 C8 C2 129.5(3) . . ?
N1 C8 C2 105.2(2) . . ?
N1 C9 C10 111.0(2) . . ?
N1 C9 H1 109.4 . . ?
C10 C9 H1 109.4 . . ?
N1 C9 H2 109.4 . . ?
C10 C9 H2 109.4 . . ?
H1 C9 H2 108.0 . . ?
C11 C10 C15 119.2(2) . . ?
C11 C10 C9 120.0(3) . . ?
C15 C10 C9 120.8(3) . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H3 119.7 . . ?
C12 C11 H3 119.7 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H4 120.1 . . ?
C11 C12 H4 120.1 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H5 120.1 . . ?
C14 C13 H5 120.1 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H6 119.6 . . ?
C15 C14 H6 119.6 . . ?
C14 C15 C10 119.8(3) . . ?
C14 C15 H7 120.1 . . ?
C10 C15 H7 120.1 . . ?
O3 C16 N2 125.1(2) . . ?
O3 C16 C3 130.2(2) . . ?
N2 C16 C3 104.7(2) . . ?
C17 N2 C16 113.9(2) . . ?
C17 N2 C18 122.6(2) . . ?
C16 N2 C18 123.4(2) . . ?
O4 C17 N2 125.1(2) . . ?
O4 C17 C4 129.6(2) . . ?
N2 C17 C4 105.3(2) . . ?
N2 C18 C19 110.5(2) . . ?
N2 C18 H8 109.5 . . ?
C19 C18 H8 109.5 . . ?
N2 C18 H9 109.5 . . ?
C19 C18 H9 109.5 . . ?
H8 C18 H9 108.1 . . ?
C24 C19 C20 118.2(3) . . ?
C24 C19 C18 121.6(2) . . ?
C20 C19 C18 120.1(2) . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H10 119.5 . . ?
C19 C20 H10 119.5 . . ?
C22 C21 C20 119.7(3) . . ?
C22 C21 H11 120.2 . . ?
C20 C21 H11 120.2 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H12 119.8 . . ?
C21 C22 H12 119.8 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H13 120.0 . . ?
C24 C23 H13 120.0 . . ?
C19 C24 C23 120.8(3) . . ?
C19 C24 H14 119.6 . . ?
C23 C24 H14 119.6 . . ?
O5 C25 N3 124.8(2) . . ?
O5 C25 C5 130.1(2) . . ?
N3 C25 C5 105.1(2) . . ?
C25 N3 C26 113.5(2) . . ?
C25 N3 C27 122.7(2) . . ?
C26 N3 C27 123.7(2) . . ?
O6 C26 N3 124.6(2) . . ?
O6 C26 C6 130.2(3) . . ?
N3 C26 C6 105.1(2) . . ?
N3 C27 C28 112.5(2) . . ?
N3 C27 H15 109.1 . . ?
C28 C27 H15 109.1 . . ?
N3 C27 H16 109.1 . . ?
C28 C27 H16 109.1 . . ?
H15 C27 H16 107.8 . . ?
C29 C28 C33 118.4(3) . . ?
C29 C28 C27 120.5(3) . . ?
C33 C28 C27 121.1(2) . . ?
C28 C29 C30 119.8(3) . . ?
C28 C29 H17 120.1 . . ?
C30 C29 H17 120.1 . . ?
C31 C30 C29 120.9(3) . . ?
C31 C30 H18 119.5 . . ?
C29 C30 H18 119.5 . . ?
C32 C31 C30 119.7(3) . . ?
C32 C31 H19 120.1 . . ?
C30 C31 H19 120.1 . . ?
C31 C32 C33 119.8(3) . . ?
C31 C32 H20 120.1 . . ?
C33 C32 H20 120.1 . . ?
C28 C33 C32 121.4(3) . . ?
C28 C33 H21 119.3 . . ?
C32 C33 H21 119.3 . . ?
C39 C34 C35 120.5(2) . . ?
C39 C34 C40 131.8(2) . . ?
C35 C34 C40 107.7(2) . . ?
C36 C35 C34 119.8(2) . . ?
C36 C35 C41 132.0(2) . . ?
C34 C35 C41 108.2(2) . . ?
C35 C36 C37 119.7(2) . . ?
C35 C36 C49 132.8(2) . . ?
C37 C36 C49 107.5(2) . . ?
C38 C37 C36 119.9(2) . . ?
C38 C37 C50 132.2(2) . . ?
C36 C37 C50 108.0(2) . . ?
C39 C38 C37 119.9(2) . . ?
C39 C38 C58 108.5(2) . . ?
C37 C38 C58 131.6(2) . . ?
C34 C39 C38 120.3(2) . . ?
C34 C39 C59 131.8(2) . . ?
C38 C39 C59 107.9(2) . . ?
O7 C40 N4 125.0(2) . . ?
O7 C40 C34 129.6(2) . . ?
N4 C40 C34 105.4(2) . . ?
C40 N4 C41 113.36(19) . . ?
C40 N4 C42 122.9(2) . . ?
C41 N4 C42 123.7(2) . . ?
O8 C41 N4 124.7(2) . . ?
O8 C41 C35 129.9(2) . . ?
N4 C41 C35 105.3(2) . . ?
N4 C42 C43 113.17(19) . . ?
N4 C42 H22 108.9 . . ?
C43 C42 H22 108.9 . . ?
N4 C42 H23 108.9 . . ?
C43 C42 H23 108.9 . . ?
H22 C42 H23 107.8 . . ?
C44 C43 C48 118.7(2) . . ?
C44 C43 C42 120.3(2) . . ?
C48 C43 C42 121.0(2) . . ?
C45 C44 C43 121.0(2) . . ?
C45 C44 H24 119.5 . . ?
C43 C44 H24 119.5 . . ?
C46 C45 C44 120.1(3) . . ?
C46 C45 H25 119.9 . . ?
C44 C45 H25 119.9 . . ?
C45 C46 C47 119.7(3) . . ?
C45 C46 H26 120.1 . . ?
C47 C46 H26 120.1 . . ?
C48 C47 C46 120.1(3) . . ?
C48 C47 H27 119.9 . . ?
C46 C47 H27 119.9 . . ?
C47 C48 C43 120.4(3) . . ?
C47 C48 H28 119.8 . . ?
C43 C48 H28 119.8 . . ?
O9 C49 N5 125.1(2) . . ?
O9 C49 C36 129.3(2) . . ?
N5 C49 C36 105.6(2) . . ?
C49 N5 C50 113.29(19) . . ?
C49 N5 C51 124.8(2) . . ?
C50 N5 C51 121.9(2) . . ?
O10 C50 N5 124.8(2) . . ?
O10 C50 C37 129.6(2) . . ?
N5 C50 C37 105.58(19) . . ?
N5 C51 C52 112.1(2) . . ?
N5 C51 H29 109.2 . . ?
C52 C51 H29 109.2 . . ?
N5 C51 H30 109.2 . . ?
C52 C51 H30 109.2 . . ?
H29 C51 H30 107.9 . . ?
C57 C52 C53 118.4(2) . . ?
C57 C52 C51 120.6(2) . . ?
C53 C52 C51 120.9(2) . . ?
C54 C53 C52 121.0(3) . . ?
C54 C53 H31 119.5 . . ?
C52 C53 H31 119.5 . . ?
C55 C54 C53 119.7(3) . . ?
C55 C54 H32 120.2 . . ?
C53 C54 H32 120.2 . . ?
C56 C55 C54 120.3(3) . . ?
C56 C55 H33 119.9 . . ?
C54 C55 H33 119.9 . . ?
C55 C56 C57 119.9(3) . . ?
C55 C56 H34 120.1 . . ?
C57 C56 H34 120.1 . . ?
C52 C57 C56 120.8(3) . . ?
C52 C57 H35 119.6 . . ?
C56 C57 H35 119.6 . . ?
O11 C58 N6 124.8(2) . . ?
O11 C58 C38 130.4(2) . . ?
N6 C58 C38 104.7(2) . . ?
C59 N6 C58 113.6(2) . . ?
C59 N6 C60 123.8(2) . . ?
C58 N6 C60 122.6(2) . . ?
O12 C59 N6 125.3(2) . . ?
O12 C59 C39 129.5(2) . . ?
N6 C59 C39 105.3(2) . . ?
N6 C60 C61 111.0(2) . . ?
N6 C60 H36 109.4 . . ?
C61 C60 H36 109.4 . . ?
N6 C60 H37 109.4 . . ?
C61 C60 H37 109.4 . . ?
H36 C60 H37 108.0 . . ?
C66 C61 C62 119.5(3) . . ?
C66 C61 C60 120.5(3) . . ?
C62 C61 C60 120.0(2) . . ?
C63 C62 C61 120.3(3) . . ?
C63 C62 H38 119.9 . . ?
C61 C62 H38 119.9 . . ?
C64 C63 C62 120.1(3) . . ?
C64 C63 H39 120.0 . . ?
C62 C63 H39 120.0 . . ?
C63 C64 C65 120.0(3) . . ?
C63 C64 H40 120.0 . . ?
C65 C64 H40 120.0 . . ?
C64 C65 C66 120.2(3) . . ?
C64 C65 H41 119.9 . . ?
C66 C65 H41 119.9 . . ?
C61 C66 C65 119.9(3) . . ?
C61 C66 H42 120.1 . . ?
C65 C66 H42 120.1 . . ?
C72 C67 C68 120.1(2) . . ?
C72 C67 C73 131.9(2) . . ?
C68 C67 C73 108.0(2) . . ?
C69 C68 C67 120.2(2) . . ?
C69 C68 C74 131.7(2) . . ?
C67 C68 C74 108.2(2) . . ?
C68 C69 C70 119.8(2) . . ?
C68 C69 C82 132.2(2) . . ?
C70 C69 C82 107.9(2) . . ?
C71 C70 C69 119.9(2) . . ?
C71 C70 C83 132.3(2) . . ?
C69 C70 C83 107.8(2) . . ?
C70 C71 C72 120.2(2) . . ?
C70 C71 C91 131.3(2) . . ?
C72 C71 C91 108.4(2) . . ?
C67 C72 C71 119.7(2) . . ?
C67 C72 C92 132.4(2) . . ?
C71 C72 C92 107.9(2) . . ?
O13 C73 N7 124.8(2) . . ?
O13 C73 C67 129.9(2) . . ?
N7 C73 C67 105.3(2) . . ?
C74 N7 C73 112.8(2) . . ?
C74 N7 C75 122.8(2) . . ?
C73 N7 C75 124.2(2) . . ?
O14 C74 N7 125.0(2) . . ?
O14 C74 C68 129.3(2) . . ?
N7 C74 C68 105.7(2) . . ?
N7 C75 C76 115.4(2) . . ?
N7 C75 H43 108.4 . . ?
C76 C75 H43 108.4 . . ?
N7 C75 H44 108.4 . . ?
C76 C75 H44 108.4 . . ?
H43 C75 H44 107.5 . . ?
C77 C76 C81 119.4(2) . . ?
C77 C76 C75 119.8(2) . . ?
C81 C76 C75 120.5(2) . . ?
C76 C77 C78 119.9(2) . . ?
C76 C77 H45 120.1 . . ?
C78 C77 H45 120.1 . . ?
C79 C78 C77 120.6(2) . . ?
C79 C78 H46 119.7 . . ?
C77 C78 H46 119.7 . . ?
C78 C79 C80 119.4(2) . . ?
C78 C79 H47 120.3 . . ?
C80 C79 H47 120.3 . . ?
C79 C80 C81 120.6(3) . . ?
C79 C80 H48 119.7 . . ?
C81 C80 H48 119.7 . . ?
C80 C81 C76 120.0(2) . . ?
C80 C81 H49 120.0 . . ?
C76 C81 H49 120.0 . . ?
O15 C82 N8 124.8(2) . . ?
O15 C82 C69 130.0(2) . . ?
N8 C82 C69 105.2(2) . . ?
C83 N8 C82 113.6(2) . . ?
C83 N8 C84 122.5(2) . . ?
C82 N8 C84 123.7(2) . . ?
O16 C83 N8 125.0(2) . . ?
O16 C83 C70 129.6(2) . . ?
N8 C83 C70 105.4(2) . . ?
N8 C84 C85 112.0(2) . . ?
N8 C84 H50 109.2 . . ?
C85 C84 H50 109.2 . . ?
N8 C84 H51 109.2 . . ?
C85 C84 H51 109.2 . . ?
H50 C84 H51 107.9 . . ?
C90 C85 C86 119.4(2) . . ?
C90 C85 C84 120.1(2) . . ?
C86 C85 C84 120.5(2) . . ?
C87 C86 C85 120.4(3) . . ?
C87 C86 H52 119.8 . . ?
C85 C86 H52 119.8 . . ?
C88 C87 C86 119.6(3) . . ?
C88 C87 H53 120.2 . . ?
C86 C87 H53 120.2 . . ?
C87 C88 C89 120.5(3) . . ?
C87 C88 H54 119.7 . . ?
C89 C88 H54 119.7 . . ?
C88 C89 C90 119.9(3) . . ?
C88 C89 H55 120.0 . . ?
C90 C89 H55 120.0 . . ?
C85 C90 C89 120.2(3) . . ?
C85 C90 H56 119.9 . . ?
C89 C90 H56 119.9 . . ?
O17 C91 N9 124.8(2) . . ?
O17 C91 C71 130.0(2) . . ?
N9 C91 C71 105.2(2) . . ?
C91 N9 C92 113.1(2) . . ?
C91 N9 C93 123.5(2) . . ?
C92 N9 C93 123.4(2) . . ?
O18 C92 N9 124.5(2) . . ?
O18 C92 C72 130.1(2) . . ?
N9 C92 C72 105.4(2) . . ?
N9 C93 C94 113.1(2) . . ?
N9 C93 H57 109.0 . . ?
C94 C93 H57 109.0 . . ?
N9 C93 H58 109.0 . . ?
C94 C93 H58 109.0 . . ?
H57 C93 H58 107.8 . . ?
C95 C94 C99 118.8(3) . . ?
C95 C94 C93 120.7(2) . . ?
C99 C94 C93 120.5(2) . . ?
C96 C95 C94 120.6(3) . . ?
C96 C95 H59 119.7 . . ?
C94 C95 H59 119.7 . . ?
C95 C96 C97 120.2(3) . . ?
C95 C96 H60 119.9 . . ?
C97 C96 H60 119.9 . . ?
C96 C97 C98 119.5(3) . . ?
C96 C97 H61 120.2 . . ?
C98 C97 H61 120.2 . . ?
C99 C98 C97 120.0(3) . . ?
C99 C98 H62 120.0 . . ?
C97 C98 H62 120.0 . . ?
C98 C99 C94 120.8(3) . . ?
C98 C99 H63 119.6 . . ?
C94 C99 H63 119.6 . . ?
C105 C100 C101 120.0(2) . . ?
C105 C100 C106 132.2(3) . . ?
C101 C100 C106 107.7(2) . . ?
C102 C101 C100 120.3(2) . . ?
C102 C101 C107 131.2(3) . . ?
C100 C101 C107 108.3(3) . . ?
C101 C102 C103 119.5(2) . . ?
C101 C102 C115 132.3(2) . . ?
C103 C102 C115 108.1(2) . . ?
C104 C103 C102 120.0(2) . . ?
C104 C103 C116 131.7(2) . . ?
C102 C103 C116 108.3(2) . . ?
C103 C104 C105 120.2(2) . . ?
C103 C104 C124 131.7(2) . . ?
C105 C104 C124 108.0(2) . . ?
C100 C105 C104 119.6(2) . . ?
C100 C105 C125 132.8(2) . . ?
C104 C105 C125 107.5(2) . . ?
O19 C106 N10 124.9(3) . . ?
O19 C106 C100 129.3(3) . . ?
N10 C106 C100 105.8(3) . . ?
C106 N10 C107 112.6(2) . . ?
C106 N10 C108 123.7(3) . . ?
C107 N10 C108 122.5(3) . . ?
O20 C107 N10 125.2(3) . . ?
O20 C107 C101 129.3(3) . . ?
N10 C107 C101 105.4(3) . . ?
N10 C108 C109 113.2(2) . . ?
N10 C108 H64 108.9 . . ?
C109 C108 H64 108.9 . . ?
N10 C108 H65 108.9 . . ?
C109 C108 H65 108.9 . . ?
H64 C108 H65 107.7 . . ?
C110 C109 C114 118.1(3) . . ?
C110 C109 C108 121.3(3) . . ?
C114 C109 C108 120.6(3) . . ?
C109 C110 C111 120.7(3) . . ?
C109 C110 H66 119.6 . . ?
C111 C110 H66 119.6 . . ?
C112 C111 C110 120.9(3) . . ?
C112 C111 H67 119.6 . . ?
C110 C111 H67 119.6 . . ?
C113 C112 C111 118.8(3) . . ?
C113 C112 H68 120.6 . . ?
C111 C112 H68 120.6 . . ?
C112 C113 C114 120.6(3) . . ?
C112 C113 H69 119.7 . . ?
C114 C113 H69 119.7 . . ?
C113 C114 C109 120.9(3) . . ?
C113 C114 H70 119.5 . . ?
C109 C114 H70 119.5 . . ?
O21 C115 N11 124.3(3) . . ?
O21 C115 C102 130.3(3) . . ?
N11 C115 C102 105.4(2) . . ?
C115 N11 C116 113.1(2) . . ?
C115 N11 C117 124.2(2) . . ?
C116 N11 C117 122.7(2) . . ?
O22 C116 N11 124.7(2) . . ?
O22 C116 C103 130.3(2) . . ?
N11 C116 C103 105.0(2) . . ?
N11 C117 C118 112.1(2) . . ?
N11 C117 H71 109.2 . . ?
C118 C117 H71 109.2 . . ?
N11 C117 H72 109.2 . . ?
C118 C117 H72 109.2 . . ?
H71 C117 H72 107.9 . . ?
C123 C118 C119 119.1(3) . . ?
C123 C118 C117 120.5(3) . . ?
C119 C118 C117 120.3(3) . . ?
C120 C119 C118 120.5(3) . . ?
C120 C119 H73 119.7 . . ?
C118 C119 H73 119.7 . . ?
C121 C120 C119 120.1(3) . . ?
C121 C120 H74 120.0 . . ?
C119 C120 H74 120.0 . . ?
C122 C121 C120 119.7(3) . . ?
C122 C121 H75 120.1 . . ?
C120 C121 H75 120.1 . . ?
C121 C122 C123 120.4(3) . . ?
C121 C122 H76 119.8 . . ?
C123 C122 H76 119.8 . . ?
C118 C123 C122 120.1(3) . . ?
C118 C123 H77 119.9 . . ?
C122 C123 H77 119.9 . . ?
O23 C124 N12 125.2(2) . . ?
O23 C124 C104 128.9(2) . . ?
N12 C124 C104 105.9(2) . . ?
C124 N12 C125 112.6(2) . . ?
C124 N12 C126 123.6(2) . . ?
C125 N12 C126 123.4(2) . . ?
O24 C125 N12 124.2(3) . . ?
O24 C125 C105 130.1(2) . . ?
N12 C125 C105 105.6(2) . . ?
N12 C126 C127 111.6(2) . . ?
N12 C126 H78 109.3 . . ?
C127 C126 H78 109.3 . . ?
N12 C126 H79 109.3 . . ?
C127 C126 H79 109.3 . . ?
H78 C126 H79 108.0 . . ?
C132 C127 C128 119.1(2) . . ?
C132 C127 C126 121.6(2) . . ?
C128 C127 C126 119.4(2) . . ?
C129 C128 C127 120.1(3) . . ?
C129 C128 H80 119.9 . . ?
C127 C128 H80 119.9 . . ?
C130 C129 C128 119.8(3) . . ?
C130 C129 H81 120.1 . . ?
C128 C129 H81 120.1 . . ?
C129 C130 C131 121.2(3) . . ?
C129 C130 H82 119.4 . . ?
C131 C130 H82 119.4 . . ?
C130 C131 C132 119.0(3) . . ?
C130 C131 H83 120.5 . . ?
C132 C131 H83 120.5 . . ?
C127 C132 C131 120.8(3) . . ?
C127 C132 H84 119.6 . . ?
C131 C132 H84 119.6 . . ?
C134 C133 H85 109.5 . . ?
C134 C133 H86 109.5 . . ?
H85 C133 H86 109.5 . . ?
C134 C133 H87 109.5 . . ?
H85 C133 H87 109.5 . . ?
H86 C133 H87 109.5 . . ?
O25 C134 C133 122.3(3) . . ?
O25 C134 C135 120.8(3) . . ?
C133 C134 C135 116.8(3) . . ?
C134 C135 H88 109.5 . . ?
C134 C135 H89 109.5 . . ?
H88 C135 H89 109.5 . . ?
C134 C135 H90 109.5 . . ?
H88 C135 H90 109.5 . . ?
H89 C135 H90 109.5 . . ?
C137 C136 H91 109.5 . . ?
C137 C136 H92 109.5 . . ?
H91 C136 H92 109.5 . . ?
C137 C136 H93 109.5 . . ?
H91 C136 H93 109.5 . . ?
H92 C136 H93 109.5 . . ?
O26 C137 C138 121.9(3) . . ?
O26 C137 C136 121.3(3) . . ?
C138 C137 C136 116.8(3) . . ?
C137 C138 H94 109.5 . . ?
C137 C138 H95 109.5 . . ?
H94 C138 H95 109.5 . . ?
C137 C138 H96 109.5 . . ?
H94 C138 H96 109.5 . . ?
H95 C138 H96 109.5 . . ?
C140 C139 H97 109.5 . . ?
C140 C139 H98 109.5 . . ?
H97 C139 H98 109.5 . . ?
C140 C139 H99 109.5 . . ?
H97 C139 H99 109.5 . . ?
H98 C139 H99 109.5 . . ?
O27 C140 C139 121.7(3) . . ?
O27 C140 C141 122.6(3) . . ?
C139 C140 C141 115.7(3) . . ?
C140 C141 H100 109.5 . . ?
C140 C141 H101 109.5 . . ?
H100 C141 H101 109.5 . . ?
C140 C141 H102 109.5 . . ?
H100 C141 H102 109.5 . . ?
H101 C141 H102 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(4) . . . . ?
C7 C1 C2 C3 177.8(2) . . . . ?
C6 C1 C2 C8 -179.7(2) . . . . ?
C7 C1 C2 C8 -1.1(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C8 C2 C3 C4 178.9(2) . . . . ?
C1 C2 C3 C16 -178.0(3) . . . . ?
C8 C2 C3 C16 0.6(5) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C16 C3 C4 C5 179.8(2) . . . . ?
C2 C3 C4 C17 -179.1(2) . . . . ?
C16 C3 C4 C17 -0.4(3) . . . . ?
C3 C4 C5 C6 -2.0(4) . . . . ?
C17 C4 C5 C6 178.2(2) . . . . ?
C3 C4 C5 C25 179.9(2) . . . . ?
C17 C4 C5 C25 0.1(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C7 C1 C6 C5 -178.3(2) . . . . ?
C2 C1 C6 C26 179.4(2) . . . . ?
C7 C1 C6 C26 1.2(5) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C25 C5 C6 C1 -180.0(2) . . . . ?
C4 C5 C6 C26 -178.1(2) . . . . ?
C25 C5 C6 C26 0.4(3) . . . . ?
C6 C1 C7 O1 -0.7(5) . . . . ?
C2 C1 C7 O1 -179.0(3) . . . . ?
C6 C1 C7 N1 179.5(3) . . . . ?
C2 C1 C7 N1 1.2(3) . . . . ?
O1 C7 N1 C8 179.4(2) . . . . ?
C1 C7 N1 C8 -0.8(3) . . . . ?
O1 C7 N1 C9 0.9(4) . . . . ?
C1 C7 N1 C9 -179.2(2) . . . . ?
C7 N1 C8 O2 179.5(2) . . . . ?
C9 N1 C8 O2 -2.0(4) . . . . ?
C7 N1 C8 C2 0.1(3) . . . . ?
C9 N1 C8 C2 178.6(2) . . . . ?
C3 C2 C8 O2 2.5(5) . . . . ?
C1 C2 C8 O2 -178.7(3) . . . . ?
C3 C2 C8 N1 -178.1(2) . . . . ?
C1 C2 C8 N1 0.7(3) . . . . ?
C8 N1 C9 C10 -82.1(3) . . . . ?
C7 N1 C9 C10 96.2(3) . . . . ?
N1 C9 C10 C11 -92.2(3) . . . . ?
N1 C9 C10 C15 86.0(3) . . . . ?
C15 C10 C11 C12 -0.9(4) . . . . ?
C9 C10 C11 C12 177.3(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C13 C14 C15 C10 0.0(4) . . . . ?
C11 C10 C15 C14 1.0(4) . . . . ?
C9 C10 C15 C14 -177.2(2) . . . . ?
C2 C3 C16 O3 -2.3(5) . . . . ?
C4 C3 C16 O3 179.2(3) . . . . ?
C2 C3 C16 N2 177.6(3) . . . . ?
C4 C3 C16 N2 -0.9(3) . . . . ?
O3 C16 N2 C17 -178.1(2) . . . . ?
C3 C16 N2 C17 1.9(3) . . . . ?
O3 C16 N2 C18 -3.2(4) . . . . ?
C3 C16 N2 C18 176.9(2) . . . . ?
C16 N2 C17 O4 178.4(2) . . . . ?
C18 N2 C17 O4 3.4(4) . . . . ?
C16 N2 C17 C4 -2.2(3) . . . . ?
C18 N2 C17 C4 -177.2(2) . . . . ?
C5 C4 C17 O4 0.7(5) . . . . ?
C3 C4 C17 O4 -179.2(2) . . . . ?
C5 C4 C17 N2 -178.7(3) . . . . ?
C3 C4 C17 N2 1.5(3) . . . . ?
C17 N2 C18 C19 84.3(3) . . . . ?
C16 N2 C18 C19 -90.3(3) . . . . ?
N2 C18 C19 C24 -88.5(3) . . . . ?
N2 C18 C19 C20 87.5(3) . . . . ?
C24 C19 C20 C21 1.4(4) . . . . ?
C18 C19 C20 C21 -174.7(3) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C20 C19 C24 C23 -1.2(4) . . . . ?
C18 C19 C24 C23 174.8(3) . . . . ?
C22 C23 C24 C19 0.4(5) . . . . ?
C4 C5 C25 O5 -0.7(5) . . . . ?
C6 C5 C25 O5 -179.0(2) . . . . ?
C4 C5 C25 N3 178.0(3) . . . . ?
C6 C5 C25 N3 -0.3(3) . . . . ?
O5 C25 N3 C26 178.8(2) . . . . ?
C5 C25 N3 C26 0.1(3) . . . . ?
O5 C25 N3 C27 1.4(4) . . . . ?
C5 C25 N3 C27 -177.4(2) . . . . ?
C25 N3 C26 O6 -178.6(2) . . . . ?
C27 N3 C26 O6 -1.2(4) . . . . ?
C25 N3 C26 C6 0.2(3) . . . . ?
C27 N3 C26 C6 177.6(2) . . . . ?
C1 C6 C26 O6 -1.3(5) . . . . ?
C5 C6 C26 O6 178.3(3) . . . . ?
C1 C6 C26 N3 -179.9(3) . . . . ?
C5 C6 C26 N3 -0.4(3) . . . . ?
C25 N3 C27 C28 -88.0(3) . . . . ?
C26 N3 C27 C28 94.8(3) . . . . ?
N3 C27 C28 C29 98.6(3) . . . . ?
N3 C27 C28 C33 -82.4(3) . . . . ?
C33 C28 C29 C30 -0.2(5) . . . . ?
C27 C28 C29 C30 178.9(3) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
C29 C30 C31 C32 -0.6(5) . . . . ?
C30 C31 C32 C33 1.0(5) . . . . ?
C29 C28 C33 C32 0.5(4) . . . . ?
C27 C28 C33 C32 -178.6(3) . . . . ?
C31 C32 C33 C28 -0.9(5) . . . . ?
C39 C34 C35 C36 -1.4(3) . . . . ?
C40 C34 C35 C36 179.6(2) . . . . ?
C39 C34 C35 C41 178.0(2) . . . . ?
C40 C34 C35 C41 -1.0(3) . . . . ?
C34 C35 C36 C37 0.1(3) . . . . ?
C41 C35 C36 C37 -179.1(2) . . . . ?
C34 C35 C36 C49 -177.6(2) . . . . ?
C41 C35 C36 C49 3.2(4) . . . . ?
C35 C36 C37 C38 0.9(3) . . . . ?
C49 C36 C37 C38 179.1(2) . . . . ?
C35 C36 C37 C50 -177.9(2) . . . . ?
C49 C36 C37 C50 0.3(3) . . . . ?
C36 C37 C38 C39 -0.5(3) . . . . ?
C50 C37 C38 C39 178.0(2) . . . . ?
C36 C37 C38 C58 -177.7(2) . . . . ?
C50 C37 C38 C58 0.7(4) . . . . ?
C35 C34 C39 C38 1.8(3) . . . . ?
C40 C34 C39 C38 -179.5(2) . . . . ?
C35 C34 C39 C59 -179.3(2) . . . . ?
C40 C34 C39 C59 -0.6(4) . . . . ?
C37 C38 C39 C34 -0.8(3) . . . . ?
C58 C38 C39 C34 177.0(2) . . . . ?
C37 C38 C39 C59 -179.9(2) . . . . ?
C58 C38 C39 C59 -2.1(3) . . . . ?
C39 C34 C40 O7 1.2(4) . . . . ?
C35 C34 C40 O7 -180.0(2) . . . . ?
C39 C34 C40 N4 -177.5(2) . . . . ?
C35 C34 C40 N4 1.3(2) . . . . ?
O7 C40 N4 C41 -180.0(2) . . . . ?
C34 C40 N4 C41 -1.2(3) . . . . ?
O7 C40 N4 C42 0.2(4) . . . . ?
C34 C40 N4 C42 179.0(2) . . . . ?
C40 N4 C41 O8 178.4(2) . . . . ?
C42 N4 C41 O8 -1.8(4) . . . . ?
C40 N4 C41 C35 0.6(3) . . . . ?
C42 N4 C41 C35 -179.6(2) . . . . ?
C36 C35 C41 O8 1.9(4) . . . . ?
C34 C35 C41 O8 -177.3(2) . . . . ?
C36 C35 C41 N4 179.6(2) . . . . ?
C34 C35 C41 N4 0.3(3) . . . . ?
C40 N4 C42 C43 91.0(3) . . . . ?
C41 N4 C42 C43 -88.9(3) . . . . ?
N4 C42 C43 C44 -102.5(3) . . . . ?
N4 C42 C43 C48 79.7(3) . . . . ?
C48 C43 C44 C45 0.6(4) . . . . ?
C42 C43 C44 C45 -177.2(2) . . . . ?
C43 C44 C45 C46 0.1(4) . . . . ?
C44 C45 C46 C47 -0.5(4) . . . . ?
C45 C46 C47 C48 0.1(4) . . . . ?
C46 C47 C48 C43 0.7(4) . . . . ?
C44 C43 C48 C47 -1.0(3) . . . . ?
C42 C43 C48 C47 176.8(2) . . . . ?
C35 C36 C49 O9 -3.7(5) . . . . ?
C37 C36 C49 O9 178.4(2) . . . . ?
C35 C36 C49 N5 176.4(2) . . . . ?
C37 C36 C49 N5 -1.5(3) . . . . ?
O9 C49 N5 C50 -177.6(2) . . . . ?
C36 C49 N5 C50 2.3(3) . . . . ?
O9 C49 N5 C51 3.1(4) . . . . ?
C36 C49 N5 C51 -176.9(2) . . . . ?
C49 N5 C50 O10 178.9(2) . . . . ?
C51 N5 C50 O10 -1.8(4) . . . . ?
C49 N5 C50 C37 -2.1(3) . . . . ?
C51 N5 C50 C37 177.1(2) . . . . ?
C38 C37 C50 O10 1.3(4) . . . . ?
C36 C37 C50 O10 179.9(2) . . . . ?
C38 C37 C50 N5 -177.6(2) . . . . ?
C36 C37 C50 N5 1.0(2) . . . . ?
C49 N5 C51 C52 -100.0(3) . . . . ?
C50 N5 C51 C52 80.9(3) . . . . ?
N5 C51 C52 C57 -100.7(3) . . . . ?
N5 C51 C52 C53 79.0(3) . . . . ?
C57 C52 C53 C54 0.5(4) . . . . ?
C51 C52 C53 C54 -179.3(3) . . . . ?
C52 C53 C54 C55 -0.5(4) . . . . ?
C53 C54 C55 C56 0.6(4) . . . . ?
C54 C55 C56 C57 -0.8(4) . . . . ?
C53 C52 C57 C56 -0.7(4) . . . . ?
C51 C52 C57 C56 179.1(2) . . . . ?
C55 C56 C57 C52 0.8(4) . . . . ?
C39 C38 C58 O11 -176.6(2) . . . . ?
C37 C38 C58 O11 0.8(4) . . . . ?
C39 C38 C58 N6 1.9(3) . . . . ?
C37 C38 C58 N6 179.4(2) . . . . ?
O11 C58 N6 C59 177.7(2) . . . . ?
C38 C58 N6 C59 -0.9(3) . . . . ?
O11 C58 N6 C60 -1.6(4) . . . . ?
C38 C58 N6 C60 179.7(2) . . . . ?
C58 N6 C59 O12 179.9(2) . . . . ?
C60 N6 C59 O12 -0.8(4) . . . . ?
C58 N6 C59 C39 -0.3(3) . . . . ?
C60 N6 C59 C39 179.0(2) . . . . ?
C34 C39 C59 O12 2.3(4) . . . . ?
C38 C39 C59 O12 -178.7(2) . . . . ?
C34 C39 C59 N6 -177.5(2) . . . . ?
C38 C39 C59 N6 1.5(3) . . . . ?
C59 N6 C60 C61 104.3(3) . . . . ?
C58 N6 C60 C61 -76.5(3) . . . . ?
N6 C60 C61 C66 -76.2(3) . . . . ?
N6 C60 C61 C62 103.3(3) . . . . ?
C66 C61 C62 C63 2.3(4) . . . . ?
C60 C61 C62 C63 -177.2(3) . . . . ?
C61 C62 C63 C64 -1.9(5) . . . . ?
C62 C63 C64 C65 0.5(5) . . . . ?
C63 C64 C65 C66 0.5(6) . . . . ?
C62 C61 C66 C65 -1.4(5) . . . . ?
C60 C61 C66 C65 178.2(3) . . . . ?
C64 C65 C66 C61 0.0(5) . . . . ?
C72 C67 C68 C69 -4.2(4) . . . . ?
C73 C67 C68 C69 176.5(2) . . . . ?
C72 C67 C68 C74 175.9(2) . . . . ?
C73 C67 C68 C74 -3.4(3) . . . . ?
C67 C68 C69 C70 1.3(3) . . . . ?
C74 C68 C69 C70 -178.8(2) . . . . ?
C67 C68 C69 C82 -174.7(2) . . . . ?
C74 C68 C69 C82 5.2(5) . . . . ?
C68 C69 C70 C71 2.1(4) . . . . ?
C82 C69 C70 C71 179.0(2) . . . . ?
C68 C69 C70 C83 -175.6(2) . . . . ?
C82 C69 C70 C83 1.3(3) . . . . ?
C69 C70 C71 C72 -2.7(4) . . . . ?
C83 C70 C71 C72 174.4(2) . . . . ?
C69 C70 C71 C91 176.1(2) . . . . ?
C83 C70 C71 C91 -6.9(5) . . . . ?
C68 C67 C72 C71 3.6(4) . . . . ?
C73 C67 C72 C71 -177.3(2) . . . . ?
C68 C67 C72 C92 -174.6(2) . . . . ?
C73 C67 C72 C92 4.5(5) . . . . ?
C70 C71 C72 C67 -0.2(4) . . . . ?
C91 C71 C72 C67 -179.1(2) . . . . ?
C70 C71 C72 C92 178.4(2) . . . . ?
C91 C71 C72 C92 -0.6(3) . . . . ?
C72 C67 C73 O13 1.2(5) . . . . ?
C68 C67 C73 O13 -179.6(3) . . . . ?
C72 C67 C73 N7 -177.4(2) . . . . ?
C68 C67 C73 N7 1.8(3) . . . . ?
O13 C73 N7 C74 -178.0(2) . . . . ?
C67 C73 N7 C74 0.7(3) . . . . ?
O13 C73 N7 C75 -3.3(4) . . . . ?
C67 C73 N7 C75 175.4(2) . . . . ?
C73 N7 C74 O14 174.3(2) . . . . ?
C75 N7 C74 O14 -0.5(4) . . . . ?
C73 N7 C74 C68 -2.7(3) . . . . ?
C75 N7 C74 C68 -177.5(2) . . . . ?
C69 C68 C74 O14 7.1(4) . . . . ?
C67 C68 C74 O14 -173.0(2) . . . . ?
C69 C68 C74 N7 -176.1(2) . . . . ?
C67 C68 C74 N7 3.8(3) . . . . ?
C74 N7 C75 C76 -79.3(3) . . . . ?
C73 N7 C75 C76 106.5(3) . . . . ?
N7 C75 C76 C77 -111.1(3) . . . . ?
N7 C75 C76 C81 74.4(3) . . . . ?
C81 C76 C77 C78 1.1(4) . . . . ?
C75 C76 C77 C78 -173.4(2) . . . . ?
C76 C77 C78 C79 -0.3(4) . . . . ?
C77 C78 C79 C80 -0.8(4) . . . . ?
C78 C79 C80 C81 1.1(4) . . . . ?
C79 C80 C81 C76 -0.3(4) . . . . ?
C77 C76 C81 C80 -0.9(4) . . . . ?
C75 C76 C81 C80 173.6(2) . . . . ?
C68 C69 C82 O15 -4.6(5) . . . . ?
C70 C69 C82 O15 179.0(3) . . . . ?
C68 C69 C82 N8 174.7(2) . . . . ?
C70 C69 C82 N8 -1.7(3) . . . . ?
O15 C82 N8 C83 -179.1(2) . . . . ?
C69 C82 N8 C83 1.5(3) . . . . ?
O15 C82 N8 C84 4.5(4) . . . . ?
C69 C82 N8 C84 -174.9(2) . . . . ?
C82 N8 C83 O16 -179.7(2) . . . . ?
C84 N8 C83 O16 -3.3(4) . . . . ?
C82 N8 C83 C70 -0.8(3) . . . . ?
C84 N8 C83 C70 175.7(2) . . . . ?
C71 C70 C83 O16 1.2(5) . . . . ?
C69 C70 C83 O16 178.5(2) . . . . ?
C71 C70 C83 N8 -177.7(3) . . . . ?
C69 C70 C83 N8 -0.4(3) . . . . ?
C83 N8 C84 C85 82.8(3) . . . . ?
C82 N8 C84 C85 -101.1(3) . . . . ?
N8 C84 C85 C90 -110.8(3) . . . . ?
N8 C84 C85 C86 67.9(3) . . . . ?
C90 C85 C86 C87 -0.4(4) . . . . ?
C84 C85 C86 C87 -179.1(2) . . . . ?
C85 C86 C87 C88 -0.2(4) . . . . ?
C86 C87 C88 C89 0.6(4) . . . . ?
C87 C88 C89 C90 -0.4(4) . . . . ?
C86 C85 C90 C89 0.5(4) . . . . ?
C84 C85 C90 C89 179.2(3) . . . . ?
C88 C89 C90 C85 -0.1(4) . . . . ?
C70 C71 C91 O17 0.7(5) . . . . ?
C72 C71 C91 O17 179.5(3) . . . . ?
C70 C71 C91 N9 -178.3(2) . . . . ?
C72 C71 C91 N9 0.6(3) . . . . ?
O17 C91 N9 C92 -179.3(2) . . . . ?
C71 C91 N9 C92 -0.4(3) . . . . ?
O17 C91 N9 C93 0.1(4) . . . . ?
C71 C91 N9 C93 179.1(2) . . . . ?
C91 N9 C92 O18 179.7(2) . . . . ?
C93 N9 C92 O18 0.3(4) . . . . ?
C91 N9 C92 C72 0.0(3) . . . . ?
C93 N9 C92 C72 -179.4(2) . . . . ?
C67 C72 C92 O18 -1.0(5) . . . . ?
C71 C72 C92 O18 -179.3(3) . . . . ?
C67 C72 C92 N9 178.7(3) . . . . ?
C71 C72 C92 N9 0.4(3) . . . . ?
C91 N9 C93 C94 -91.1(3) . . . . ?
C92 N9 C93 C94 88.2(3) . . . . ?
N9 C93 C94 C95 80.0(3) . . . . ?
N9 C93 C94 C99 -99.6(3) . . . . ?
C99 C94 C95 C96 0.5(4) . . . . ?
C93 C94 C95 C96 -179.1(2) . . . . ?
C94 C95 C96 C97 -0.4(4) . . . . ?
C95 C96 C97 C98 -0.2(4) . . . . ?
C96 C97 C98 C99 0.6(4) . . . . ?
C97 C98 C99 C94 -0.5(4) . . . . ?
C95 C94 C99 C98 -0.1(4) . . . . ?
C93 C94 C99 C98 179.5(2) . . . . ?
C105 C100 C101 C102 -2.3(4) . . . . ?
C106 C100 C101 C102 -178.9(2) . . . . ?
C105 C100 C101 C107 173.2(2) . . . . ?
C106 C100 C101 C107 -3.4(3) . . . . ?
C100 C101 C102 C103 5.6(4) . . . . ?
C107 C101 C102 C103 -168.7(3) . . . . ?
C100 C101 C102 C115 -175.2(3) . . . . ?
C107 C101 C102 C115 10.5(5) . . . . ?
C101 C102 C103 C104 -3.6(4) . . . . ?
C115 C102 C103 C104 177.1(2) . . . . ?
C101 C102 C103 C116 177.6(2) . . . . ?
C115 C102 C103 C116 -1.8(3) . . . . ?
C102 C103 C104 C105 -1.8(4) . . . . ?
C116 C103 C104 C105 176.8(2) . . . . ?
C102 C103 C104 C124 176.7(2) . . . . ?
C116 C103 C104 C124 -4.8(5) . . . . ?
C101 C100 C105 C104 -3.0(4) . . . . ?
C106 C100 C105 C104 172.6(3) . . . . ?
C101 C100 C105 C125 179.8(3) . . . . ?
C106 C100 C105 C125 -4.6(5) . . . . ?
C103 C104 C105 C100 5.1(4) . . . . ?
C124 C104 C105 C100 -173.7(2) . . . . ?
C103 C104 C105 C125 -177.1(2) . . . . ?
C124 C104 C105 C125 4.1(3) . . . . ?
C105 C100 C106 O19 3.4(5) . . . . ?
C101 C100 C106 O19 179.4(3) . . . . ?
C105 C100 C106 N10 -174.6(3) . . . . ?
C101 C100 C106 N10 1.4(3) . . . . ?
O19 C106 N10 C107 -176.7(3) . . . . ?
C100 C106 N10 C107 1.4(3) . . . . ?
O19 C106 N10 C108 -8.8(4) . . . . ?
C100 C106 N10 C108 169.3(2) . . . . ?
C106 N10 C107 O20 173.5(3) . . . . ?
C108 N10 C107 O20 5.5(4) . . . . ?
C106 N10 C107 C101 -3.4(3) . . . . ?
C108 N10 C107 C101 -171.5(2) . . . . ?
C102 C101 C107 O20 2.3(5) . . . . ?
C100 C101 C107 O20 -172.5(3) . . . . ?
C102 C101 C107 N10 179.0(3) . . . . ?
C100 C101 C107 N10 4.2(3) . . . . ?
C106 N10 C108 C109 99.5(3) . . . . ?
C107 N10 C108 C109 -93.8(3) . . . . ?
N10 C108 C109 C110 -90.9(4) . . . . ?
N10 C108 C109 C114 90.5(3) . . . . ?
C114 C109 C110 C111 -2.0(4) . . . . ?
C108 C109 C110 C111 179.4(3) . . . . ?
C109 C110 C111 C112 0.0(4) . . . . ?
C110 C111 C112 C113 1.3(4) . . . . ?
C111 C112 C113 C114 -0.7(4) . . . . ?
C112 C113 C114 C109 -1.3(4) . . . . ?
C110 C109 C114 C113 2.6(4) . . . . ?
C108 C109 C114 C113 -178.8(3) . . . . ?
C101 C102 C115 O21 2.4(5) . . . . ?
C103 C102 C115 O21 -178.4(3) . . . . ?
C101 C102 C115 N11 -179.3(3) . . . . ?
C103 C102 C115 N11 -0.1(3) . . . . ?
O21 C115 N11 C116 -179.4(2) . . . . ?
C102 C115 N11 C116 2.1(3) . . . . ?
O21 C115 N11 C117 -0.6(4) . . . . ?
C102 C115 N11 C117 -179.1(2) . . . . ?
C115 N11 C116 O22 175.8(2) . . . . ?
C117 N11 C116 O22 -3.1(4) . . . . ?
C115 N11 C116 C103 -3.2(3) . . . . ?
C117 N11 C116 C103 178.0(2) . . . . ?
C104 C103 C116 O22 5.4(5) . . . . ?
C102 C103 C116 O22 -175.9(3) . . . . ?
C104 C103 C116 N11 -175.7(3) . . . . ?
C102 C103 C116 N11 3.0(3) . . . . ?
C115 N11 C117 C118 -92.6(3) . . . . ?
C116 N11 C117 C118 86.0(3) . . . . ?
N11 C117 C118 C123 -99.0(3) . . . . ?
N11 C117 C118 C119 79.2(3) . . . . ?
C123 C118 C119 C120 0.9(4) . . . . ?
C117 C118 C119 C120 -177.4(2) . . . . ?
C118 C119 C120 C121 0.6(4) . . . . ?
C119 C120 C121 C122 -1.0(4) . . . . ?
C120 C121 C122 C123 0.0(4) . . . . ?
C119 C118 C123 C122 -1.9(4) . . . . ?
C117 C118 C123 C122 176.4(2) . . . . ?
C121 C122 C123 C118 1.5(4) . . . . ?
C103 C104 C124 O23 -7.2(5) . . . . ?
C105 C104 C124 O23 171.4(2) . . . . ?
C103 C104 C124 N12 175.8(3) . . . . ?
C105 C104 C124 N12 -5.6(3) . . . . ?
O23 C124 N12 C125 -172.1(2) . . . . ?
C104 C124 N12 C125 5.1(3) . . . . ?
O23 C124 N12 C126 1.1(4) . . . . ?
C104 C124 N12 C126 178.2(2) . . . . ?
C124 N12 C125 O24 176.6(2) . . . . ?
C126 N12 C125 O24 3.4(4) . . . . ?
C124 N12 C125 C105 -2.6(3) . . . . ?
C126 N12 C125 C105 -175.7(2) . . . . ?
C100 C105 C125 O24 -2.9(5) . . . . ?
C104 C105 C125 O24 179.7(3) . . . . ?
C100 C105 C125 N12 176.3(3) . . . . ?
C104 C105 C125 N12 -1.2(3) . . . . ?
C124 N12 C126 C127 -98.2(3) . . . . ?
C125 N12 C126 C127 74.3(3) . . . . ?
N12 C126 C127 C132 -108.9(3) . . . . ?
N12 C126 C127 C128 70.6(3) . . . . ?
C132 C127 C128 C129 -1.1(4) . . . . ?
C126 C127 C128 C129 179.4(2) . . . . ?
C127 C128 C129 C130 0.1(4) . . . . ?
C128 C129 C130 C131 0.2(4) . . . . ?
C129 C130 C131 C132 0.5(4) . . . . ?
C128 C127 C132 C131 1.9(4) . . . . ?
C126 C127 C132 C131 -178.6(2) . . . . ?
C130 C131 C132 C127 -1.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050

#===END


#==============================================================================

#     End of CIF

#==============================================================================
####################################################################### 
# 
# 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_H-aniline
_database_code_depnum_ccdc_archive 'CCDC 1557864'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H21 N3 O6, C6 H7 N'
_chemical_formula_sum            'C39 H28 N4 O6'
_chemical_formula_weight         648.65

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   11.279(8)
_cell_length_b                   11.279(8)
_cell_length_c                   42.69(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4703(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    7045
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      30.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2028
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13494
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         3.89
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1905
_reflns_number_gt                1811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0896P)²+6.5298P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1905
_refine_ls_number_parameters     178
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1632
_refine_ls_wR_factor_gt          0.1589
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8098(2) 0.4125(2) 0.13446(4) 0.0199(5) Uani 1 1 d . . .
C2 C 0.9623(2) 0.4683(2) 0.13137(5) 0.0235(5) Uani 1 1 d . . .
N1 N 0.97854(17) 0.35306(18) 0.12918(4) 0.0243(4) Uani 1 1 d . . .
C3 C 0.8548(2) 0.2287(2) 0.13172(4) 0.0221(5) Uani 1 1 d . . .
C4 C 0.7451(2) 0.2680(2) 0.13440(4) 0.0206(5) Uani 1 1 d . . .
O1 O 1.05482(15) 0.58651(16) 0.13073(4) 0.0310(4) Uani 1 1 d . . .
O2 O 0.84444(16) 0.11614(16) 0.13168(3) 0.0278(4) Uani 1 1 d . . .
C5 C 1.1115(2) 0.3610(2) 0.12336(5) 0.0272(5) Uani 1 1 d . . .
H5 H 1.1138 0.2852 0.1345 0.033 Uiso 1 1 calc R . .
H5A H 1.1862 0.4484 0.1318 0.033 Uiso 1 1 calc R . .
C6 C 1.1346(2) 0.3519(2) 0.08845(5) 0.0263(5) Uani 1 1 d . . .
C7 C 1.1611(2) 0.4607(3) 0.06835(5) 0.0335(6) Uani 1 1 d . . .
H7 H 1.1671 0.5418 0.0766 0.040 Uiso 1 1 calc R . .
C8 C 1.1786(3) 0.4509(3) 0.03624(6) 0.0394(6) Uani 1 1 d . . .
H8 H 1.1946 0.5244 0.0227 0.047 Uiso 1 1 calc R . .
C9 C 1.1728(2) 0.3338(3) 0.02401(5) 0.0391(6) Uani 1 1 d . . .
H9 H 1.1865 0.3278 0.0022 0.047 Uiso 1 1 calc R . .
C10 C 1.1469(3) 0.2256(3) 0.04381(6) 0.0394(6) Uani 1 1 d . . .
H10 H 1.1423 0.1453 0.0355 0.047 Uiso 1 1 calc R . .
C11 C 1.1275(2) 0.2345(3) 0.07593(5) 0.0319(6) Uani 1 1 d . . .
H11 H 1.1095 0.1600 0.0893 0.038 Uiso 1 1 calc R . .
C12 C 0.7106(9) 0.4264(5) 0.05612(10) 0.0357(11) Uani 0.33 1 d PGU A -1
C13 C 0.8072(7) 0.3842(7) 0.05569(14) 0.0364(11) Uani 0.33 1 d PGU A -1
H13 H 0.9019 0.4499 0.0570 0.044 Uiso 0.33 1 calc PR A -1
C14 C 0.7651(8) 0.2457(7) 0.05334(13) 0.0372(11) Uani 0.33 1 d PGU A -1
H14 H 0.8310 0.2168 0.0530 0.045 Uiso 0.33 1 calc PR A -1
C15 C 0.6264(9) 0.1496(5) 0.05142(12) 0.0367(11) Uani 0.33 1 d PGU A -1
H15 H 0.5977 0.0549 0.0498 0.044 Uiso 0.33 1 calc PR A -1
C16 C 0.5299(7) 0.1918(7) 0.05185(13) 0.0363(11) Uani 0.33 1 d PGU A -1
H16 H 0.4352 0.1261 0.0505 0.044 Uiso 0.33 1 calc PR A -1
C17 C 0.5720(8) 0.3303(7) 0.05420(11) 0.0353(11) Uani 0.33 1 d PGU A -1
H17 H 0.5060 0.3591 0.0545 0.042 Uiso 0.33 1 calc PR A -1
N2 N 0.7537(9) 0.5637(8) 0.06234(16) 0.0492(19) Uani 0.33 1 d P A -1
H2 H 0.8408 0.6220 0.0659 0.074 Uiso 0.33 1 calc PR A -1
H2A H 0.6937 0.5920 0.0627 0.074 Uiso 0.33 1 calc PR A -1


_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 C4 1.393(3) 2_655 ?
C1 C4 1.414(3) . ?
C1 C2 1.513(3) . ?
C2 O1 1.215(3) . ?
C2 N1 1.403(3) . ?
N1 C3 1.403(3) . ?
N1 C5 1.478(3) . ?
C3 O2 1.215(3) . ?
C3 C4 1.514(3) . ?
C4 C1 1.393(3) 3_665 ?
C5 C6 1.525(3) . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C11 1.392(3) . ?
C6 C7 1.402(3) . ?
C7 C8 1.397(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.400(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C12 N2 1.398(8) . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N2 H2 0.8800 . ?
N2 H2A 0.8800 . ?

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
C4 C1 C4 120.3(2) 2_655 . ?
C4 C1 C2 131.70(18) 2_655 . ?
C4 C1 C2 107.71(17) . . ?
O1 C2 N1 125.21(19) . . ?
O1 C2 C1 129.2(2) . . ?
N1 C2 C1 105.56(17) . . ?
C3 N1 C2 113.29(16) . . ?
C3 N1 C5 123.04(18) . . ?
C2 N1 C5 123.62(17) . . ?
O2 C3 N1 124.90(18) . . ?
O2 C3 C4 129.84(19) . . ?
N1 C3 C4 105.26(16) . . ?
C1 C4 C1 119.7(2) 3_665 . ?
C1 C4 C3 132.01(18) 3_665 . ?
C1 C4 C3 108.11(17) . . ?
N1 C5 C6 111.26(17) . . ?
N1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
H5 C5 H5A 108.0 . . ?
C11 C6 C7 118.9(2) . . ?
C11 C6 C5 120.6(2) . . ?
C7 C6 C5 120.5(2) . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 120.5(2) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C17 120.0 . . ?
C13 C12 N2 119.0(6) . . ?
C17 C12 N2 120.5(6) . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.0 . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C12 N2 H2 120.0 . . ?
C12 N2 H2A 120.0 . . ?
H2 N2 H2A 120.0 . . ?

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
C4 C1 C2 O1 7.0(4) 2_655 . . . ?
C4 C1 C2 O1 -179.3(2) . . . . ?
C4 C1 C2 N1 -172.79(19) 2_655 . . . ?
C4 C1 C2 N1 0.9(2) . . . . ?
O1 C2 N1 C3 177.80(19) . . . . ?
C1 C2 N1 C3 -2.4(2) . . . . ?
O1 C2 N1 C5 -4.8(3) . . . . ?
C1 C2 N1 C5 175.05(17) . . . . ?
C2 N1 C3 O2 -177.08(18) . . . . ?
C5 N1 C3 O2 5.5(3) . . . . ?
C2 N1 C3 C4 2.8(2) . . . . ?
C5 N1 C3 C4 -174.64(16) . . . . ?
C4 C1 C4 C1 -0.4(4) 2_655 . . 3_665 ?
C2 C1 C4 C1 -174.89(13) . . . 3_665 ?
C4 C1 C4 C3 175.27(13) 2_655 . . . ?
C2 C1 C4 C3 0.7(2) . . . . ?
O2 C3 C4 C1 -7.3(3) . . . 3_665 ?
N1 C3 C4 C1 172.80(19) . . . 3_665 ?
O2 C3 C4 C1 177.77(19) . . . . ?
N1 C3 C4 C1 -2.1(2) . . . . ?
C3 N1 C5 C6 84.8(2) . . . . ?
C2 N1 C5 C6 -92.4(2) . . . . ?
N1 C5 C6 C11 -108.1(2) . . . . ?
N1 C5 C6 C7 70.9(3) . . . . ?
C11 C6 C7 C8 0.7(3) . . . . ?
C5 C6 C7 C8 -178.3(2) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C7 C8 C9 C10 1.2(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C7 C6 C11 C10 0.1(3) . . . . ?
C5 C6 C11 C10 179.1(2) . . . . ?
C9 C10 C11 C6 -0.3(4) . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
N2 C12 C13 C14 172.2(5) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C12 0.0 . . . . ?
C13 C12 C17 C16 0.0 . . . . ?
N2 C12 C17 C16 -172.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_F
_database_code_depnum_ccdc_archive 'CCDC 1557867'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H18 F3 N3 O6'
_chemical_formula_sum            'C33 H18 F3 N3 O6'
_chemical_formula_weight         609.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   11.791(11)
_cell_length_b                   10.595(8)
_cell_length_c                   11.856(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.406(13)
_cell_angle_gamma                90.00
_cell_volume                     1388(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    93
_cell_measurement_reflns_used    3804
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.1

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18809
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.13
_reflns_number_total             4904
_reflns_number_gt                3965
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0807P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4904
_refine_ls_number_parameters     407
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1524
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1336(5) 1.3817(4) 0.4090(5) 0.0288(12) Uani 1 1 d . . .
C1 C 0.0426(6) 1.3124(5) 0.3232(6) 0.0280(15) Uani 1 1 d . . .
C2 C 0.0658(6) 1.1766(6) 0.3646(5) 0.0257(14) Uani 1 1 d . . .
C3 C -0.0001(6) 1.0669(5) 0.3201(5) 0.0234(14) Uani 1 1 d . . .
C4 C -0.1115(6) 1.0424(6) 0.2146(6) 0.0314(15) Uani 1 1 d . . .
N2 N -0.1384(5) 0.9154(5) 0.2242(5) 0.0275(13) Uani 1 1 d . . .
C5 C -0.0566(6) 0.8546(6) 0.3203(5) 0.0265(14) Uani 1 1 d . . .
C6 C 0.0346(6) 0.9541(6) 0.3866(6) 0.0252(14) Uani 1 1 d . . .
C7 C 0.1323(6) 0.9533(6) 0.4925(5) 0.0274(15) Uani 1 1 d . . .
C8 C 0.1857(5) 0.8507(6) 0.5843(6) 0.0247(14) Uani 1 1 d . . .
N3 N 0.2764(5) 0.9088(5) 0.6773(5) 0.0277(13) Uani 1 1 d . . .
C9 C 0.2936(6) 1.0362(6) 0.6556(6) 0.0299(16) Uani 1 1 d . . .
C10 C 0.1989(6) 1.0634(6) 0.5356(6) 0.0253(14) Uani 1 1 d . . .
C11 C 0.1651(6) 1.1748(6) 0.4716(6) 0.0270(14) Uani 1 1 d . . .
C12 C 0.2117(6) 1.3074(6) 0.5019(6) 0.0288(15) Uani 1 1 d . . .
O1 O 0.2937(4) 1.3473(4) 0.5865(4) 0.0359(11) Uani 1 1 d . . .
O2 O -0.0355(4) 1.3567(4) 0.2377(4) 0.0342(11) Uani 1 1 d . . .
O3 O -0.1706(4) 1.1144(4) 0.1375(4) 0.0335(11) Uani 1 1 d . . .
O4 O -0.0601(4) 0.7447(4) 0.3467(4) 0.0280(10) Uani 1 1 d . . .
O5 O 0.1539(4) 0.7420(4) 0.5827(4) 0.0278(10) Uani 1 1 d . . .
O6 O 0.3696(4) 1.1034(4) 0.7211(4) 0.0318(11) Uani 1 1 d . . .
C13 C 0.1368(7) 1.5213(5) 0.4118(7) 0.0364(17) Uani 1 1 d . . .
H13 H 0.1709 1.5493 0.4967 0.044 Uiso 1 1 calc R . .
H13A H 0.0529 1.5534 0.3780 0.044 Uiso 1 1 calc R . .
C14 C 0.2104(6) 1.5795(5) 0.3427(6) 0.0284(15) Uani 1 1 d . . .
C15 C 0.3257(6) 1.6251(6) 0.4002(6) 0.0354(17) Uani 1 1 d . . .
H15 H 0.3624 1.6149 0.4848 0.042 Uiso 1 1 calc R . .
C16 C 0.3898(6) 1.6861(7) 0.3367(6) 0.0340(16) Uani 1 1 d . . .
H16 H 0.4678 1.7204 0.3774 0.041 Uiso 1 1 calc R . .
C17 C 0.3375(6) 1.6953(6) 0.2151(6) 0.0320(16) Uani 1 1 d . . .
C18 C 0.2230(7) 1.6522(7) 0.1540(7) 0.045(2) Uani 1 1 d . . .
H18 H 0.1871 1.6630 0.0694 0.054 Uiso 1 1 calc R . .
C19 C 0.1611(7) 1.5928(7) 0.2182(7) 0.044(2) Uani 1 1 d . . .
H19 H 0.0827 1.5600 0.1764 0.053 Uiso 1 1 calc R . .
F1 F 0.3983(4) 1.7560(4) 0.1524(4) 0.0460(11) Uani 1 1 d . . .
C20 C -0.2449(6) 0.8490(7) 0.1374(6) 0.0294(15) Uani 1 1 d . . .
H20 H -0.2989 0.9117 0.0827 0.035 Uiso 1 1 calc R . .
H20A H -0.2909 0.8067 0.1824 0.035 Uiso 1 1 calc R . .
C21 C -0.2071(6) 0.7519(7) 0.0637(6) 0.0320(16) Uani 1 1 d . . .
C22 C -0.1237(6) 0.7802(6) 0.0076(6) 0.0350(16) Uani 1 1 d . . .
H22 H -0.0926 0.8635 0.0128 0.042 Uiso 1 1 calc R . .
C23 C -0.0855(6) 0.6896(7) -0.0553(6) 0.0374(17) Uani 1 1 d . . .
H23 H -0.0287 0.7093 -0.0931 0.045 Uiso 1 1 calc R . .
C24 C -0.1325(6) 0.5702(7) -0.0611(6) 0.0358(17) Uani 1 1 d . . .
C25 C -0.2163(6) 0.5376(7) -0.0101(6) 0.0352(16) Uani 1 1 d . . .
H25 H -0.2485 0.4545 -0.0181 0.042 Uiso 1 1 calc R . .
C26 C -0.2530(6) 0.6302(6) 0.0543(6) 0.0328(16) Uani 1 1 d . . .
H26 H -0.3098 0.6095 0.0919 0.039 Uiso 1 1 calc R . .
F2 F -0.0948(4) 0.4803(4) -0.1229(4) 0.0444(10) Uani 1 1 d . . .
C27 C 0.3489(6) 0.8392(7) 0.7855(6) 0.0294(15) Uani 1 1 d . . .
H27 H 0.2955 0.7842 0.8125 0.035 Uiso 1 1 calc R . .
H27A H 0.3891 0.8995 0.8511 0.035 Uiso 1 1 calc R . .
C28 C 0.4441(6) 0.7591(6) 0.7593(6) 0.0272(14) Uani 1 1 d . . .
C29 C 0.4288(6) 0.6268(6) 0.7537(6) 0.0299(16) Uani 1 1 d . . .
H29 H 0.3635 0.5889 0.7705 0.036 Uiso 1 1 calc R . .
C30 C 0.5115(6) 0.5529(7) 0.7229(6) 0.0348(16) Uani 1 1 d . . .
H30 H 0.5025 0.4638 0.7179 0.042 Uiso 1 1 calc R . .
C31 C 0.6060(6) 0.6093(7) 0.6997(6) 0.0343(16) Uani 1 1 d . . .
C32 C 0.6249(7) 0.7381(8) 0.7060(7) 0.0451(19) Uani 1 1 d . . .
H32 H 0.6907 0.7751 0.6893 0.054 Uiso 1 1 calc R . .
C33 C 0.5417(6) 0.8119(6) 0.7384(6) 0.0353(17) Uani 1 1 d . . .
H33 H 0.5533 0.9007 0.7461 0.042 Uiso 1 1 calc R . .
F3 F 0.6870(4) 0.5362(4) 0.6705(4) 0.0522(12) 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
N1 C1 1.402(8) . ?
N1 C12 1.404(9) . ?
N1 C13 1.479(7) . ?
C1 O2 1.202(8) . ?
C1 C2 1.514(8) . ?
C2 C11 1.394(9) . ?
C2 C3 1.396(9) . ?
C3 C6 1.411(9) . ?
C3 C4 1.487(9) . ?
C4 O3 1.207(8) . ?
C4 N2 1.397(9) . ?
N2 C5 1.370(8) . ?
N2 C20 1.493(8) . ?
C5 O4 1.210(8) . ?
C5 C6 1.514(9) . ?
C6 C7 1.377(9) . ?
C7 C10 1.399(9) . ?
C7 C8 1.512(9) . ?
C8 O5 1.209(8) . ?
C8 N3 1.384(8) . ?
N3 C9 1.402(9) . ?
N3 C27 1.469(8) . ?
C9 O6 1.195(8) . ?
C9 C10 1.499(9) . ?
C10 C11 1.385(9) . ?
C11 C12 1.505(9) . ?
C12 O1 1.202(8) . ?
C13 C14 1.516(10) . ?
C13 H13 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.379(9) . ?
C14 C19 1.392(10) . ?
C15 C16 1.397(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.359(10) . ?
C16 H16 0.9500 . ?
C17 F1 1.361(7) . ?
C17 C18 1.369(10) . ?
C18 C19 1.377(10) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.514(10) . ?
C20 H20 0.9900 . ?
C20 H20A 0.9900 . ?
C21 C26 1.387(10) . ?
C21 C22 1.399(10) . ?
C22 C23 1.384(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.373(11) . ?
C23 H23 0.9500 . ?
C24 F2 1.366(8) . ?
C24 C25 1.371(11) . ?
C25 C26 1.402(9) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.523(10) . ?
C27 H27 0.9900 . ?
C27 H27A 0.9900 . ?
C28 C33 1.377(10) . ?
C28 C29 1.412(9) . ?
C29 C30 1.395(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.374(9) . ?
C30 H30 0.9500 . ?
C31 F3 1.365(8) . ?
C31 C32 1.380(10) . ?
C32 C33 1.409(10) . ?
C32 H32 0.9500 . ?
C33 H33 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
C1 N1 C12 113.7(4) . . ?
C1 N1 C13 123.2(6) . . ?
C12 N1 C13 122.5(6) . . ?
O2 C1 N1 125.1(5) . . ?
O2 C1 C2 130.1(6) . . ?
N1 C1 C2 104.8(5) . . ?
C11 C2 C3 120.9(6) . . ?
C11 C2 C1 107.9(6) . . ?
C3 C2 C1 130.9(6) . . ?
C2 C3 C6 118.6(5) . . ?
C2 C3 C4 132.5(6) . . ?
C6 C3 C4 108.7(5) . . ?
O3 C4 N2 125.7(6) . . ?
O3 C4 C3 129.3(6) . . ?
N2 C4 C3 105.0(6) . . ?
C5 N2 C4 114.0(5) . . ?
C5 N2 C20 122.1(5) . . ?
C4 N2 C20 123.9(5) . . ?
O4 C5 N2 126.1(6) . . ?
O4 C5 C6 128.1(6) . . ?
N2 C5 C6 105.8(5) . . ?
C7 C6 C3 120.1(6) . . ?
C7 C6 C5 133.3(7) . . ?
C3 C6 C5 106.5(5) . . ?
C6 C7 C10 120.9(7) . . ?
C6 C7 C8 131.8(6) . . ?
C10 C7 C8 107.3(5) . . ?
O5 C8 N3 125.8(6) . . ?
O5 C8 C7 128.7(6) . . ?
N3 C8 C7 105.4(5) . . ?
C8 N3 C9 113.8(5) . . ?
C8 N3 C27 121.7(5) . . ?
C9 N3 C27 124.5(6) . . ?
O6 C9 N3 125.4(6) . . ?
O6 C9 C10 130.1(6) . . ?
N3 C9 C10 104.6(6) . . ?
C11 C10 C7 119.5(6) . . ?
C11 C10 C9 131.4(6) . . ?
C7 C10 C9 108.9(6) . . ?
C10 C11 C2 120.0(6) . . ?
C10 C11 C12 130.8(6) . . ?
C2 C11 C12 109.0(6) . . ?
O1 C12 N1 125.0(6) . . ?
O1 C12 C11 130.4(6) . . ?
N1 C12 C11 104.5(5) . . ?
N1 C13 C14 114.2(6) . . ?
N1 C13 H13 108.7 . . ?
C14 C13 H13 108.7 . . ?
N1 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
H13 C13 H13A 107.6 . . ?
C15 C14 C19 117.6(6) . . ?
C15 C14 C13 121.8(6) . . ?
C19 C14 C13 120.5(6) . . ?
C14 C15 C16 121.4(7) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 118.3(7) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C16 C17 F1 118.9(6) . . ?
C16 C17 C18 122.4(6) . . ?
F1 C17 C18 118.6(6) . . ?
C17 C18 C19 118.4(7) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C18 C19 C14 121.8(7) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
N2 C20 C21 111.8(5) . . ?
N2 C20 H20 109.2 . . ?
C21 C20 H20 109.2 . . ?
N2 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
H20 C20 H20A 107.9 . . ?
C26 C21 C22 118.7(7) . . ?
C26 C21 C20 119.5(6) . . ?
C22 C21 C20 121.7(6) . . ?
C23 C22 C21 121.5(6) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 117.7(7) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
F2 C24 C25 118.7(7) . . ?
F2 C24 C23 117.9(7) . . ?
C25 C24 C23 123.4(7) . . ?
C24 C25 C26 118.1(7) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C21 C26 C25 120.6(7) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
N3 C27 C28 110.3(5) . . ?
N3 C27 H27 109.6 . . ?
C28 C27 H27 109.6 . . ?
N3 C27 H27A 109.6 . . ?
C28 C27 H27A 109.6 . . ?
H27 C27 H27A 108.1 . . ?
C33 C28 C29 119.7(6) . . ?
C33 C28 C27 122.1(6) . . ?
C29 C28 C27 118.1(6) . . ?
C30 C29 C28 118.7(7) . . ?
C30 C29 H29 120.7 . . ?
C28 C29 H29 120.7 . . ?
C31 C30 C29 119.9(6) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
F3 C31 C30 119.4(6) . . ?
F3 C31 C32 117.5(6) . . ?
C30 C31 C32 123.1(7) . . ?
C31 C32 C33 116.7(7) . . ?
C31 C32 H32 121.6 . . ?
C33 C32 H32 121.6 . . ?
C28 C33 C32 121.9(6) . . ?
C28 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?

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
C12 N1 C1 O2 178.3(6) . . . . ?
C13 N1 C1 O2 6.8(11) . . . . ?
C12 N1 C1 C2 -0.9(7) . . . . ?
C13 N1 C1 C2 -172.5(6) . . . . ?
O2 C1 C2 C11 -177.8(7) . . . . ?
N1 C1 C2 C11 1.4(8) . . . . ?
O2 C1 C2 C3 -4.3(12) . . . . ?
N1 C1 C2 C3 174.9(7) . . . . ?
C11 C2 C3 C6 1.0(10) . . . . ?
C1 C2 C3 C6 -171.7(7) . . . . ?
C11 C2 C3 C4 176.0(7) . . . . ?
C1 C2 C3 C4 3.3(13) . . . . ?
C2 C3 C4 O3 3.1(13) . . . . ?
C6 C3 C4 O3 178.5(7) . . . . ?
C2 C3 C4 N2 -174.9(7) . . . . ?
C6 C3 C4 N2 0.5(7) . . . . ?
O3 C4 N2 C5 -179.9(7) . . . . ?
C3 C4 N2 C5 -1.7(7) . . . . ?
O3 C4 N2 C20 1.2(11) . . . . ?
C3 C4 N2 C20 179.3(6) . . . . ?
C4 N2 C5 O4 -179.5(7) . . . . ?
C20 N2 C5 O4 -0.5(10) . . . . ?
C4 N2 C5 C6 2.2(7) . . . . ?
C20 N2 C5 C6 -178.8(6) . . . . ?
C2 C3 C6 C7 -0.6(9) . . . . ?
C4 C3 C6 C7 -176.7(6) . . . . ?
C2 C3 C6 C5 176.9(6) . . . . ?
C4 C3 C6 C5 0.8(7) . . . . ?
O4 C5 C6 C7 -3.0(12) . . . . ?
N2 C5 C6 C7 175.3(7) . . . . ?
O4 C5 C6 C3 179.9(6) . . . . ?
N2 C5 C6 C3 -1.8(7) . . . . ?
C3 C6 C7 C10 -0.3(10) . . . . ?
C5 C6 C7 C10 -177.0(6) . . . . ?
C3 C6 C7 C8 176.5(6) . . . . ?
C5 C6 C7 C8 -0.3(13) . . . . ?
C6 C7 C8 O5 1.8(12) . . . . ?
C10 C7 C8 O5 178.9(6) . . . . ?
C6 C7 C8 N3 -174.5(7) . . . . ?
C10 C7 C8 N3 2.5(7) . . . . ?
O5 C8 N3 C9 -179.4(6) . . . . ?
C7 C8 N3 C9 -3.0(7) . . . . ?
O5 C8 N3 C27 2.6(10) . . . . ?
C7 C8 N3 C27 179.0(6) . . . . ?
C8 N3 C9 O6 -177.0(6) . . . . ?
C27 N3 C9 O6 0.9(11) . . . . ?
C8 N3 C9 C10 2.2(7) . . . . ?
C27 N3 C9 C10 -179.9(6) . . . . ?
C6 C7 C10 C11 0.8(10) . . . . ?
C8 C7 C10 C11 -176.7(6) . . . . ?
C6 C7 C10 C9 176.2(6) . . . . ?
C8 C7 C10 C9 -1.3(7) . . . . ?
O6 C9 C10 C11 -6.7(13) . . . . ?
N3 C9 C10 C11 174.2(7) . . . . ?
O6 C9 C10 C7 178.7(7) . . . . ?
N3 C9 C10 C7 -0.4(7) . . . . ?
C7 C10 C11 C2 -0.4(10) . . . . ?
C9 C10 C11 C2 -174.5(7) . . . . ?
C7 C10 C11 C12 173.5(6) . . . . ?
C9 C10 C11 C12 -0.7(12) . . . . ?
C3 C2 C11 C10 -0.5(11) . . . . ?
C1 C2 C11 C10 173.7(6) . . . . ?
C3 C2 C11 C12 -175.6(6) . . . . ?
C1 C2 C11 C12 -1.3(8) . . . . ?
C1 N1 C12 O1 -177.8(7) . . . . ?
C13 N1 C12 O1 -6.2(10) . . . . ?
C1 N1 C12 C11 0.1(7) . . . . ?
C13 N1 C12 C11 171.7(6) . . . . ?
C10 C11 C12 O1 4.2(13) . . . . ?
C2 C11 C12 O1 178.6(7) . . . . ?
C10 C11 C12 N1 -173.6(7) . . . . ?
C2 C11 C12 N1 0.8(8) . . . . ?
C1 N1 C13 C14 -92.5(8) . . . . ?
C12 N1 C13 C14 96.6(8) . . . . ?
N1 C13 C14 C15 -101.8(8) . . . . ?
N1 C13 C14 C19 80.6(8) . . . . ?
C19 C14 C15 C16 2.0(10) . . . . ?
C13 C14 C15 C16 -175.7(6) . . . . ?
C14 C15 C16 C17 -2.6(10) . . . . ?
C15 C16 C17 F1 179.2(5) . . . . ?
C15 C16 C17 C18 3.0(10) . . . . ?
C16 C17 C18 C19 -2.8(11) . . . . ?
F1 C17 C18 C19 -178.9(6) . . . . ?
C17 C18 C19 C14 2.1(12) . . . . ?
C15 C14 C19 C18 -1.7(11) . . . . ?
C13 C14 C19 C18 176.0(6) . . . . ?
C5 N2 C20 C21 -67.6(8) . . . . ?
C4 N2 C20 C21 111.3(7) . . . . ?
N2 C20 C21 C26 130.1(6) . . . . ?
N2 C20 C21 C22 -47.7(8) . . . . ?
C26 C21 C22 C23 -0.7(10) . . . . ?
C20 C21 C22 C23 177.1(6) . . . . ?
C21 C22 C23 C24 0.1(10) . . . . ?
C22 C23 C24 F2 -179.8(6) . . . . ?
C22 C23 C24 C25 1.3(11) . . . . ?
F2 C24 C25 C26 179.2(6) . . . . ?
C23 C24 C25 C26 -1.9(10) . . . . ?
C22 C21 C26 C25 0.0(10) . . . . ?
C20 C21 C26 C25 -177.8(6) . . . . ?
C24 C25 C26 C21 1.2(10) . . . . ?
C8 N3 C27 C28 77.4(8) . . . . ?
C9 N3 C27 C28 -100.3(7) . . . . ?
N3 C27 C28 C33 69.6(8) . . . . ?
N3 C27 C28 C29 -108.9(7) . . . . ?
C33 C28 C29 C30 -2.2(10) . . . . ?
C27 C28 C29 C30 176.3(6) . . . . ?
C28 C29 C30 C31 0.5(10) . . . . ?
C29 C30 C31 F3 179.5(6) . . . . ?
C29 C30 C31 C32 0.4(11) . . . . ?
F3 C31 C32 C33 -178.9(6) . . . . ?
C30 C31 C32 C33 0.3(11) . . . . ?
C29 C28 C33 C32 2.9(10) . . . . ?
C27 C28 C33 C32 -175.5(6) . . . . ?
C31 C32 C33 C28 -2.0(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.13
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_F-ethylacetate
_database_code_depnum_ccdc_archive 'CCDC 1557873'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H18 F3 N3 O6, C4 H8 O2'
_chemical_formula_sum            'C37 H26 F3 N3 O8'
_chemical_formula_weight         697.61

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'
O O 0.0106 0.0060 '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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.935(2)
_cell_length_b                   10.508(2)
_cell_length_c                   27.362(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.943(3)
_cell_angle_gamma                90.00
_cell_volume                     3380.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    8168
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      31.1

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            54292
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         27.49
_reflns_number_total             7764
_reflns_number_gt                5930
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1096P)²+2.1534P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7764
_refine_ls_number_parameters     679
_refine_ls_number_restraints     262
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.2068
_refine_ls_wR_factor_gt          0.1861
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.13926(18) 0.5263(2) 0.62426(8) 0.0287(5) Uani 1 1 d . . .
N1 N 0.11392(15) 0.39969(17) 0.63272(7) 0.0279(4) Uani 1 1 d . . .
C2 C 0.18973(18) 0.3452(2) 0.67120(8) 0.0263(4) Uani 1 1 d . . .
C3 C 0.27040(18) 0.4494(2) 0.69139(8) 0.0256(4) Uani 1 1 d . . .
C4 C 0.35910(18) 0.4536(2) 0.73145(8) 0.0258(4) Uani 1 1 d . . .
C5 C 0.40881(18) 0.3556(2) 0.76899(8) 0.0274(4) Uani 1 1 d . . .
N2 N 0.49156(15) 0.41852(18) 0.80185(7) 0.0289(4) Uani 1 1 d . . .
C6 C 0.50384(18) 0.5462(2) 0.78967(8) 0.0288(5) Uani 1 1 d . . .
C7 C 0.41633(18) 0.5686(2) 0.74427(8) 0.0270(4) Uani 1 1 d . . .
C8 C 0.38420(19) 0.6773(2) 0.71688(8) 0.0289(5) Uani 1 1 d . . .
C9 C 0.4202(2) 0.8137(2) 0.72458(9) 0.0310(5) Uani 1 1 d . . .
N3 N 0.35281(16) 0.88095(18) 0.68678(7) 0.0320(4) Uani 1 1 d . A .
C10 C 0.27539(19) 0.8050(2) 0.65620(9) 0.0305(5) Uani 1 1 d . . .
C11 C 0.29546(18) 0.6720(2) 0.67596(8) 0.0276(4) Uani 1 1 d . . .
C12 C 0.23952(18) 0.5591(2) 0.66328(8) 0.0265(4) Uani 1 1 d . . .
O1 O 0.08801(14) 0.59225(16) 0.59148(6) 0.0352(4) Uani 1 1 d . . .
O2 O 0.18754(13) 0.23540(14) 0.68426(6) 0.0306(4) Uani 1 1 d . . .
O3 O 0.38382(14) 0.24446(15) 0.77173(6) 0.0308(4) Uani 1 1 d . . .
O4 O 0.57268(14) 0.61856(16) 0.81202(6) 0.0345(4) Uani 1 1 d . . .
O5 O 0.49017(15) 0.86092(16) 0.75672(7) 0.0377(4) Uani 1 1 d . . .
O6 O 0.20459(15) 0.84305(16) 0.62229(7) 0.0407(4) Uani 1 1 d . . .
C13 C 0.01995(19) 0.3285(2) 0.60344(9) 0.0335(5) Uani 1 1 d . . .
H13 H -0.0398 0.3888 0.5882 0.040 Uiso 1 1 calc R . .
H13A H -0.0138 0.2709 0.6256 0.040 Uiso 1 1 calc R . .
C14 C 0.0602(2) 0.2511(2) 0.56301(8) 0.0325(5) Uani 1 1 d . . .
C15 C 0.0758(2) 0.3076(2) 0.51914(9) 0.0408(6) Uani 1 1 d . . .
H15 H 0.0577 0.3951 0.5137 0.049 Uiso 1 1 calc R . .
C16 C 0.1174(3) 0.2389(3) 0.48300(10) 0.0462(6) Uani 1 1 d . . .
H16 H 0.1274 0.2778 0.4527 0.055 Uiso 1 1 calc R . .
C17 C 0.1440(2) 0.1126(3) 0.49209(9) 0.0432(6) Uani 1 1 d . . .
C18 C 0.1278(3) 0.0521(3) 0.53502(10) 0.0507(7) Uani 1 1 d . . .
H18 H 0.1451 -0.0357 0.5401 0.061 Uiso 1 1 calc R . .
C19 C 0.0857(3) 0.1226(2) 0.57046(10) 0.0434(6) Uani 1 1 d . . .
H19 H 0.0741 0.0828 0.6004 0.052 Uiso 1 1 calc R . .
F1 F 0.18500(18) 0.04453(17) 0.45684(6) 0.0599(5) Uani 1 1 d . . .
C20 C 0.5595(2) 0.3554(2) 0.84519(8) 0.0317(5) Uani 1 1 d . . .
H20 H 0.5077 0.3128 0.8646 0.038 Uiso 1 1 calc R . .
H20A H 0.6032 0.4205 0.8667 0.038 Uiso 1 1 calc R . .
C21 C 0.64085(19) 0.2585(2) 0.83052(8) 0.0304(5) Uani 1 1 d . . .
C22 C 0.6306(2) 0.1311(2) 0.84195(10) 0.0378(5) Uani 1 1 d . . .
H22 H 0.5716 0.1053 0.8591 0.045 Uiso 1 1 calc R . .
C23 C 0.7045(2) 0.0405(3) 0.82890(10) 0.0415(6) Uani 1 1 d . . .
H23 H 0.6975 -0.0466 0.8371 0.050 Uiso 1 1 calc R . .
C24 C 0.7880(2) 0.0806(2) 0.80375(9) 0.0365(5) Uani 1 1 d . . .
C25 C 0.8008(2) 0.2055(3) 0.79107(9) 0.0381(5) Uani 1 1 d . . .
H25 H 0.8589 0.2301 0.7733 0.046 Uiso 1 1 calc R . .
C26 C 0.7265(2) 0.2949(2) 0.80493(9) 0.0364(5) Uani 1 1 d . . .
H26 H 0.7344 0.3820 0.7968 0.044 Uiso 1 1 calc R . .
F2 F 0.86118(13) -0.00781(15) 0.79017(6) 0.0478(4) Uani 1 1 d . . .
C27 C 0.3595(2) 1.0196(2) 0.68155(11) 0.0430(6) Uani 1 1 d . . .
H27A H 0.3617 1.0608 0.7143 0.052 Uiso 0.301(3) 1 calc PR A 1
H27B H 0.2914 1.0510 0.6588 0.052 Uiso 0.301(3) 1 calc PR A 1
H27C H 0.2872 1.0473 0.6609 0.052 Uiso 0.264(3) 1 calc PR B 2
H27D H 0.3611 1.0565 0.7150 0.052 Uiso 0.264(3) 1 calc PR B 2
H27E H 0.3663 1.0593 0.7148 0.052 Uiso 0.440(3) 1 calc PR C 3
H27F H 0.2881 1.0506 0.6612 0.052 Uiso 0.440(3) 1 calc PR C 3
C28A C 0.4734(9) 1.0557(11) 0.6596(3) 0.0294(17) Uani 0.301(3) 1 d PDU A 1
C29A C 0.5604(11) 1.1241(12) 0.6881(3) 0.0270(18) Uani 0.301(3) 1 d PDU A 1
H29A H 0.5563 1.1421 0.7218 0.032 Uiso 0.301(3) 1 calc PR A 1
C30A C 0.6531(9) 1.1666(10) 0.6684(3) 0.0283(17) Uani 0.301(3) 1 d PDU A 1
H30A H 0.7054 1.2254 0.6862 0.034 Uiso 0.301(3) 1 calc PR A 1
C31A C 0.6682(7) 1.1216(9) 0.6224(3) 0.0323(15) Uani 0.301(3) 1 d PDU A 1
C32A C 0.5854(6) 1.0477(8) 0.5938(3) 0.0321(14) Uani 0.301(3) 1 d PDU A 1
H32A H 0.5937 1.0224 0.5613 0.039 Uiso 0.301(3) 1 calc PR A 1
C33A C 0.4904(6) 1.0111(8) 0.6133(3) 0.0318(15) Uani 0.301(3) 1 d PDU A 1
H33A H 0.4363 0.9551 0.5950 0.038 Uiso 0.301(3) 1 calc PR A 1
F3A F 0.7605(7) 1.1568(12) 0.6035(5) 0.040(2) Uani 0.301(3) 1 d PDU A 1
C28B C 0.4429(11) 1.0743(18) 0.6628(5) 0.103(4) Uani 0.264(3) 1 d PGDU A 2
C29B C 0.5519(12) 1.0941(19) 0.6892(4) 0.104(4) Uani 0.264(3) 1 d PGDU A 2
H29B H 0.5703 1.0679 0.7229 0.125 Uiso 0.264(3) 1 calc PR B 2
C30B C 0.6339(10) 1.1520(18) 0.6664(4) 0.106(4) Uani 0.264(3) 1 d PGDU A 2
H30B H 0.7084 1.1655 0.6844 0.127 Uiso 0.264(3) 1 calc PR B 2
C31B C 0.6070(10) 1.1903(18) 0.6171(4) 0.108(3) Uani 0.264(3) 1 d PGDU A 2
C32B C 0.4981(10) 1.1706(17) 0.5907(4) 0.107(3) Uani 0.264(3) 1 d PGDU A 2
H32B H 0.4797 1.1968 0.5570 0.129 Uiso 0.264(3) 1 calc PR B 2
C33B C 0.4160(9) 1.1126(16) 0.6136(5) 0.106(3) Uani 0.264(3) 1 d PGDU A 2
H33B H 0.3415 1.0992 0.5955 0.127 Uiso 0.264(3) 1 calc PR B 2
F3B F 0.6840(11) 1.2545(16) 0.5962(4) 0.121(4) Uani 0.264(3) 1 d PDU A 2
C28C C 0.4584(6) 1.0612(7) 0.6580(2) 0.0338(14) Uani 0.440(3) 1 d PGDU A 3
C29C C 0.5539(8) 1.1096(8) 0.68867(18) 0.0298(15) Uani 0.440(3) 1 d PGDU A 3
H29C H 0.5546 1.1173 0.7233 0.036 Uiso 0.440(3) 1 calc PR C 3
C30C C 0.6483(6) 1.1465(7) 0.6687(2) 0.0335(15) Uani 0.440(3) 1 d PGDU A 3
H30C H 0.7136 1.1795 0.6897 0.040 Uiso 0.440(3) 1 calc PR C 3
C31C C 0.6472(5) 1.1351(5) 0.6180(2) 0.0380(14) Uani 0.440(3) 1 d PGDU A 3
C32C C 0.5517(5) 1.0868(6) 0.58729(18) 0.0421(12) Uani 0.440(3) 1 d PGDU A 3
H32C H 0.5510 1.0791 0.5526 0.051 Uiso 0.440(3) 1 calc PR C 3
C33C C 0.4573(5) 1.0499(6) 0.6073(2) 0.0412(13) Uani 0.440(3) 1 d PGDU A 3
H33C H 0.3920 1.0169 0.5863 0.049 Uiso 0.440(3) 1 calc PR C 3
F3C F 0.7361(5) 1.1768(8) 0.5983(3) 0.0425(17) Uani 0.440(3) 1 d PDU A 3
O90A O 0.5965(4) 1.3413(5) 0.5327(2) 0.0338(12) Uani 0.301(3) 1 d PU A 1
O91A O 0.7568(5) 1.4618(5) 0.5423(2) 0.0368(14) Uani 0.301(3) 1 d PU A 1
C90A C 0.7054(7) 1.3703(7) 0.5252(3) 0.0297(13) Uani 0.301(3) 1 d PU A 1
C91A C 0.7496(7) 1.2723(9) 0.4948(3) 0.0258(17) Uani 0.301(3) 1 d PU A 1
H91A H 0.8049 1.3111 0.4767 0.039 Uiso 0.301(3) 1 calc PR A 1
H91B H 0.6866 1.2363 0.4712 0.039 Uiso 0.301(3) 1 calc PR A 1
H91C H 0.7867 1.2047 0.5165 0.039 Uiso 0.301(3) 1 calc PR A 1
C92A C 0.5445(7) 1.4370(9) 0.5617(3) 0.0415(15) Uani 0.301(3) 1 d PU A 1
H92A H 0.5179 1.5113 0.5407 0.050 Uiso 0.301(3) 1 calc PR A 1
H92B H 0.6010 1.4666 0.5903 0.050 Uiso 0.301(3) 1 calc PR A 1
C93A C 0.4431(10) 1.3731(11) 0.5803(4) 0.048(2) Uani 0.301(3) 1 d PU A 1
H93A H 0.3853 1.3495 0.5518 0.072 Uiso 0.301(3) 1 calc PR A 1
H93B H 0.4103 1.4326 0.6015 0.072 Uiso 0.301(3) 1 calc PR A 1
H93C H 0.4695 1.2966 0.5993 0.072 Uiso 0.301(3) 1 calc PR A 1
O90B O 0.4505(5) 1.4866(7) 0.4170(2) 0.0340(13) Uani 0.264(3) 1 d PU B 2
O91B O 0.5414(15) 1.312(2) 0.3911(7) 0.036(2) Uani 0.264(3) 1 d PU B 2
C90B C 0.4704(7) 1.3598(9) 0.4139(3) 0.0306(14) Uani 0.264(3) 1 d PU B 2
C91B C 0.3877(9) 1.2924(12) 0.4372(4) 0.033(2) Uani 0.264(3) 1 d PU B 2
H91D H 0.3135 1.3343 0.4288 0.050 Uiso 0.264(3) 1 calc PR B 2
H91E H 0.4122 1.2931 0.4733 0.050 Uiso 0.264(3) 1 calc PR B 2
H91F H 0.3815 1.2043 0.4253 0.050 Uiso 0.264(3) 1 calc PR B 2
C92B C 0.5205(7) 1.5702(10) 0.3948(4) 0.0341(15) Uani 0.264(3) 1 d PU B 2
H92C H 0.4765 1.6478 0.3834 0.041 Uiso 0.264(3) 1 calc PR B 2
H92D H 0.5415 1.5283 0.3652 0.041 Uiso 0.264(3) 1 calc PR B 2
C93B C 0.6245(8) 1.6073(10) 0.4283(3) 0.0360(19) Uani 0.264(3) 1 d PU B 2
H93D H 0.6046 1.6472 0.4580 0.054 Uiso 0.264(3) 1 calc PR B 2
H93E H 0.6673 1.6679 0.4114 0.054 Uiso 0.264(3) 1 calc PR B 2
H93F H 0.6712 1.5317 0.4379 0.054 Uiso 0.264(3) 1 calc PR B 2
O90C O 0.5904(4) 1.2287(5) 0.47658(17) 0.0600(12) Uani 0.440(3) 1 d PU C 3
O91C O 0.5634(10) 1.2999(15) 0.3991(4) 0.047(2) Uani 0.440(3) 1 d PU C 3
C90C C 0.5252(7) 1.2554(8) 0.4328(3) 0.0606(14) Uani 0.440(3) 1 d PU C 3
C91C C 0.4021(9) 1.2331(11) 0.4329(4) 0.068(2) Uani 0.440(3) 1 d PU C 3
H91G H 0.3931 1.1588 0.4535 0.102 Uiso 0.440(3) 1 calc PR C 3
H91H H 0.3629 1.2178 0.3989 0.102 Uiso 0.440(3) 1 calc PR C 3
H91I H 0.3693 1.3081 0.4464 0.102 Uiso 0.440(3) 1 calc PR C 3
C92C C 0.7138(8) 1.2584(11) 0.4838(3) 0.0533(16) Uani 0.440(3) 1 d PU C 3
H92E H 0.7554 1.1987 0.5085 0.064 Uiso 0.440(3) 1 calc PR C 3
H92F H 0.7415 1.2452 0.4521 0.064 Uiso 0.440(3) 1 calc PR C 3
C93C C 0.7380(6) 1.3846(8) 0.5002(3) 0.0534(16) Uani 0.440(3) 1 d PU C 3
H93G H 0.6989 1.4441 0.4754 0.080 Uiso 0.440(3) 1 calc PR C 3
H93H H 0.8203 1.3993 0.5047 0.080 Uiso 0.440(3) 1 calc PR C 3
H93I H 0.7118 1.3978 0.5318 0.080 Uiso 0.440(3) 1 calc PR C 3


_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 O1 1.212(3) . ?
C1 N1 1.392(3) . ?
C1 C12 1.500(3) . ?
N1 C2 1.388(3) . ?
N1 C13 1.466(3) . ?
C2 O2 1.210(3) . ?
C2 C3 1.499(3) . ?
C3 C4 1.387(3) . ?
C3 C12 1.399(3) . ?
C4 C7 1.403(3) . ?
C4 C5 1.502(3) . ?
C5 O3 1.211(3) . ?
C5 N2 1.383(3) . ?
N2 C6 1.396(3) . ?
N2 C20 1.474(3) . ?
C6 O4 1.206(3) . ?
C6 C7 1.497(3) . ?
C7 C8 1.384(3) . ?
C8 C11 1.403(3) . ?
C8 C9 1.500(3) . ?
C9 O5 1.210(3) . ?
C9 N3 1.389(3) . ?
N3 C10 1.387(3) . ?
N3 C27 1.468(3) . ?
C10 O6 1.210(3) . ?
C10 C11 1.503(3) . ?
C11 C12 1.376(3) . ?
C13 C14 1.517(3) . ?
C13 H13 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.381(3) . ?
C14 C19 1.391(3) . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9500 . ?
C17 F1 1.358(3) . ?
C17 C18 1.378(4) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.509(3) . ?
C20 H20 0.9900 . ?
C20 H20A 0.9900 . ?
C21 C22 1.384(3) . ?
C21 C26 1.389(3) . ?
C22 C23 1.386(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.372(4) . ?
C23 H23 0.9500 . ?
C24 F2 1.370(3) . ?
C24 C25 1.372(4) . ?
C25 C26 1.389(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28B 1.327(8) . ?
C27 C28C 1.504(6) . ?
C27 C28A 1.623(9) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 H27C 0.9900 . ?
C27 H27D 0.9900 . ?
C27 H27E 0.9900 . ?
C27 H27F 0.9900 . ?
C28A C29A 1.386(4) . ?
C28A C33A 1.397(4) . ?
C29A C30A 1.385(4) . ?
C29A H29A 0.9500 . ?
C30A C31A 1.386(4) . ?
C30A H30A 0.9500 . ?
C31A F3A 1.346(4) . ?
C31A C32A 1.387(4) . ?
C32A C33A 1.390(4) . ?
C32A H32A 0.9500 . ?
C33A H33A 0.9500 . ?
C28B C29B 1.3900 . ?
C28B C33B 1.3900 . ?
C29B C30B 1.3900 . ?
C29B H29B 0.9500 . ?
C30B C31B 1.3900 . ?
C30B H30B 0.9500 . ?
C31B F3B 1.344(5) . ?
C31B C32B 1.3900 . ?
C32B C33B 1.3900 . ?
C32B H32B 0.9500 . ?
C33B H33B 0.9500 . ?
C28C C29C 1.3900 . ?
C28C C33C 1.3900 . ?
C29C C30C 1.3900 . ?
C29C H29C 0.9500 . ?
C30C C31C 1.3900 . ?
C30C H30C 0.9500 . ?
C31C F3C 1.344(4) . ?
C31C C32C 1.3900 . ?
C32C C33C 1.3900 . ?
C32C H32C 0.9500 . ?
C33C H33C 0.9500 . ?
O90A C90A 1.383(10) . ?
O90A C92A 1.483(10) . ?
O91A C90A 1.192(10) . ?
C90A C91A 1.477(11) . ?
C91A H91A 0.9800 . ?
C91A H91B 0.9800 . ?
C91A H91C 0.9800 . ?
C92A C93A 1.543(14) . ?
C92A H92A 0.9900 . ?
C92A H92B 0.9900 . ?
C93A H93A 0.9800 . ?
C93A H93B 0.9800 . ?
C93A H93C 0.9800 . ?
O90B C90B 1.359(11) . ?
O90B C92B 1.418(12) . ?
O91B C90B 1.24(2) . ?
C90B C91B 1.449(15) . ?
C91B H91D 0.9800 . ?
C91B H91E 0.9800 . ?
C91B H91F 0.9800 . ?
C92B C93B 1.462(13) . ?
C92B H92C 0.9900 . ?
C92B H92D 0.9900 . ?
C93B H93D 0.9800 . ?
C93B H93E 0.9800 . ?
C93B H93F 0.9800 . ?
O90C C90C 1.341(9) . ?
O90C C92C 1.485(10) . ?
O91C C90C 1.192(16) . ?
C90C C91C 1.488(12) . ?
C91C H91G 0.9800 . ?
C91C H91H 0.9800 . ?
C91C H91I 0.9800 . ?
C92C C93C 1.414(13) . ?
C92C H92E 0.9900 . ?
C92C H92F 0.9900 . ?
C93C H93G 0.9800 . ?
C93C H93H 0.9800 . ?
C93C H93I 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 125.0(2) . . ?
O1 C1 C12 129.4(2) . . ?
N1 C1 C12 105.69(17) . . ?
C2 N1 C1 112.85(18) . . ?
C2 N1 C13 122.78(18) . . ?
C1 N1 C13 124.33(18) . . ?
O2 C2 N1 125.0(2) . . ?
O2 C2 C3 129.3(2) . . ?
N1 C2 C3 105.77(17) . . ?
C4 C3 C12 120.1(2) . . ?
C4 C3 C2 131.97(19) . . ?
C12 C3 C2 107.90(18) . . ?
C3 C4 C7 119.82(19) . . ?
C3 C4 C5 132.5(2) . . ?
C7 C4 C5 107.56(18) . . ?
O3 C5 N2 125.2(2) . . ?
O3 C5 C4 129.1(2) . . ?
N2 C5 C4 105.69(18) . . ?
C5 N2 C6 113.36(18) . . ?
C5 N2 C20 122.69(19) . . ?
C6 N2 C20 123.95(19) . . ?
O4 C6 N2 125.1(2) . . ?
O4 C6 C7 129.7(2) . . ?
N2 C6 C7 105.20(18) . . ?
C8 C7 C4 119.9(2) . . ?
C8 C7 C6 131.9(2) . . ?
C4 C7 C6 108.17(18) . . ?
C7 C8 C11 120.0(2) . . ?
C7 C8 C9 131.8(2) . . ?
C11 C8 C9 107.99(19) . . ?
O5 C9 N3 124.8(2) . . ?
O5 C9 C8 129.7(2) . . ?
N3 C9 C8 105.47(19) . . ?
C10 N3 C9 113.34(19) . . ?
C10 N3 C27 123.7(2) . . ?
C9 N3 C27 122.9(2) . . ?
O6 C10 N3 125.2(2) . . ?
O6 C10 C11 129.0(2) . . ?
N3 C10 C11 105.66(19) . . ?
C12 C11 C8 120.2(2) . . ?
C12 C11 C10 132.1(2) . . ?
C8 C11 C10 107.52(19) . . ?
C11 C12 C3 120.1(2) . . ?
C11 C12 C1 132.1(2) . . ?
C3 C12 C1 107.71(19) . . ?
N1 C13 C14 111.32(19) . . ?
N1 C13 H13 109.4 . . ?
C14 C13 H13 109.4 . . ?
N1 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
H13 C13 H13A 108.0 . . ?
C15 C14 C19 119.1(2) . . ?
C15 C14 C13 120.7(2) . . ?
C19 C14 C13 120.2(2) . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 118.3(2) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
F1 C17 C16 118.6(2) . . ?
F1 C17 C18 118.9(2) . . ?
C16 C17 C18 122.5(3) . . ?
C17 C18 C19 118.2(2) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C18 C19 C14 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
N2 C20 C21 112.31(18) . . ?
N2 C20 H20 109.1 . . ?
C21 C20 H20 109.1 . . ?
N2 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
H20 C20 H20A 107.9 . . ?
C22 C21 C26 118.8(2) . . ?
C22 C21 C20 120.4(2) . . ?
C26 C21 C20 120.8(2) . . ?
C21 C22 C23 121.4(2) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 117.9(2) . . ?
C24 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?
F2 C24 C25 118.4(2) . . ?
F2 C24 C23 118.7(2) . . ?
C25 C24 C23 122.8(2) . . ?
C24 C25 C26 118.3(2) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C28B C27 N3 121.7(9) . . ?
C28B C27 C28C 8.9(10) . . ?
N3 C27 C28C 113.0(3) . . ?
C28B C27 C28A 12.5(10) . . ?
N3 C27 C28A 109.4(5) . . ?
C28C C27 C28A 5.3(7) . . ?
C28B C27 H27A 104.8 . . ?
N3 C27 H27A 109.8 . . ?
C28C C27 H27A 111.1 . . ?
C28A C27 H27A 109.8 . . ?
C28B C27 H27B 101.7 . . ?
N3 C27 H27B 109.8 . . ?
C28C C27 H27B 104.7 . . ?
C28A C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
C28B C27 H27C 106.9 . . ?
N3 C27 H27C 106.9 . . ?
C28C C27 H27C 110.0 . . ?
C28A C27 H27C 115.1 . . ?
H27A C27 H27C 105.7 . . ?
H27B C27 H27C 5.3 . . ?
C28B C27 H27D 106.9 . . ?
N3 C27 H27D 106.9 . . ?
C28C C27 H27D 113.0 . . ?
C28A C27 H27D 111.5 . . ?
H27A C27 H27D 2.9 . . ?
H27B C27 H27D 109.4 . . ?
H27C C27 H27D 106.7 . . ?
C28B C27 H27E 103.0 . . ?
N3 C27 H27E 109.0 . . ?
C28C C27 H27E 109.0 . . ?
C28A C27 H27E 107.5 . . ?
H27A C27 H27E 3.3 . . ?
H27B C27 H27E 111.4 . . ?
H27C C27 H27E 108.9 . . ?
H27D C27 H27E 4.0 . . ?
C28B C27 H27F 105.7 . . ?
N3 C27 H27F 109.0 . . ?
C28C C27 H27F 109.0 . . ?
C28A C27 H27F 114.2 . . ?
H27A C27 H27F 104.6 . . ?
H27B C27 H27F 4.7 . . ?
H27C C27 H27F 2.1 . . ?
H27D C27 H27F 105.7 . . ?
H27E C27 H27F 107.8 . . ?
C29A C28A C33A 118.2(5) . . ?
C29A C28A C27 120.4(6) . . ?
C33A C28A C27 121.2(6) . . ?
C30A C29A C28A 121.3(5) . . ?
C30A C29A H29A 119.4 . . ?
C28A C29A H29A 119.4 . . ?
C29A C30A C31A 118.8(5) . . ?
C29A C30A H30A 120.6 . . ?
C31A C30A H30A 120.6 . . ?
F3A C31A C30A 119.9(5) . . ?
F3A C31A C32A 119.2(5) . . ?
C30A C31A C32A 120.8(4) . . ?
C31A C32A C33A 119.2(4) . . ?
C31A C32A H32A 120.4 . . ?
C33A C32A H32A 120.4 . . ?
C32A C33A C28A 120.8(5) . . ?
C32A C33A H33A 119.6 . . ?
C28A C33A H33A 119.6 . . ?
C27 C28B C29B 124.1(8) . . ?
C27 C28B C33B 115.9(8) . . ?
C29B C28B C33B 120.0 . . ?
C30B C29B C28B 120.0 . . ?
C30B C29B H29B 120.0 . . ?
C28B C29B H29B 120.0 . . ?
C31B C30B C29B 120.0 . . ?
C31B C30B H30B 120.0 . . ?
C29B C30B H30B 120.0 . . ?
F3B C31B C30B 119.8(5) . . ?
F3B C31B C32B 120.0(5) . . ?
C30B C31B C32B 120.0 . . ?
C33B C32B C31B 120.0 . . ?
C33B C32B H32B 120.0 . . ?
C31B C32B H32B 120.0 . . ?
C32B C33B C28B 120.0 . . ?
C32B C33B H33B 120.0 . . ?
C28B C33B H33B 120.0 . . ?
C29C C28C C33C 120.0 . . ?
C29C C28C C27 118.0(4) . . ?
C33C C28C C27 122.0(4) . . ?
C28C C29C C30C 120.0 . . ?
C28C C29C H29C 120.0 . . ?
C30C C29C H29C 120.0 . . ?
C29C C30C C31C 120.0 . . ?
C29C C30C H30C 120.0 . . ?
C31C C30C H30C 120.0 . . ?
F3C C31C C32C 119.9(3) . . ?
F3C C31C C30C 120.0(3) . . ?
C32C C31C C30C 120.0 . . ?
C31C C32C C33C 120.0 . . ?
C31C C32C H32C 120.0 . . ?
C33C C32C H32C 120.0 . . ?
C32C C33C C28C 120.0 . . ?
C32C C33C H33C 120.0 . . ?
C28C C33C H33C 120.0 . . ?
C90A O90A C92A 114.8(6) . . ?
O91A C90A O90A 123.7(7) . . ?
O91A C90A C91A 124.9(8) . . ?
O90A C90A C91A 111.4(7) . . ?
O90A C92A C93A 107.8(8) . . ?
O90A C92A H92A 110.2 . . ?
C93A C92A H92A 110.2 . . ?
O90A C92A H92B 110.2 . . ?
C93A C92A H92B 110.2 . . ?
H92A C92A H92B 108.5 . . ?
C90B O90B C92B 117.3(7) . . ?
O91B C90B O90B 124.6(13) . . ?
O91B C90B C91B 127.0(14) . . ?
O90B C90B C91B 108.2(7) . . ?
C90B C91B H91D 109.5 . . ?
C90B C91B H91E 109.5 . . ?
H91D C91B H91E 109.5 . . ?
C90B C91B H91F 109.5 . . ?
H91D C91B H91F 109.5 . . ?
H91E C91B H91F 109.5 . . ?
O90B C92B C93B 113.3(8) . . ?
O90B C92B H92C 108.9 . . ?
C93B C92B H92C 108.9 . . ?
O90B C92B H92D 108.9 . . ?
C93B C92B H92D 108.9 . . ?
H92C C92B H92D 107.7 . . ?
C92B C93B H93D 109.5 . . ?
C92B C93B H93E 109.5 . . ?
H93D C93B H93E 109.5 . . ?
C92B C93B H93F 109.5 . . ?
H93D C93B H93F 109.5 . . ?
H93E C93B H93F 109.5 . . ?
C90C O90C C92C 119.0(6) . . ?
O91C C90C O90C 122.3(8) . . ?
O91C C90C C91C 124.9(9) . . ?
O90C C90C C91C 112.7(7) . . ?
C93C C92C O90C 112.5(8) . . ?
C93C C92C H92E 109.1 . . ?
O90C C92C H92E 109.1 . . ?
C93C C92C H92F 109.1 . . ?
O90C C92C H92F 109.1 . . ?
H92E C92C H92F 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C2 177.0(2) . . . . ?
C12 C1 N1 C2 -2.9(2) . . . . ?
O1 C1 N1 C13 -1.0(3) . . . . ?
C12 C1 N1 C13 179.03(19) . . . . ?
C1 N1 C2 O2 -177.3(2) . . . . ?
C13 N1 C2 O2 0.7(3) . . . . ?
C1 N1 C2 C3 2.6(2) . . . . ?
C13 N1 C2 C3 -179.36(18) . . . . ?
O2 C2 C3 C4 -4.4(4) . . . . ?
N1 C2 C3 C4 175.7(2) . . . . ?
O2 C2 C3 C12 178.8(2) . . . . ?
N1 C2 C3 C12 -1.1(2) . . . . ?
C12 C3 C4 C7 1.2(3) . . . . ?
C2 C3 C4 C7 -175.3(2) . . . . ?
C12 C3 C4 C5 177.6(2) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 O3 3.0(4) . . . . ?
C7 C4 C5 O3 179.7(2) . . . . ?
C3 C4 C5 N2 -176.3(2) . . . . ?
C7 C4 C5 N2 0.4(2) . . . . ?
O3 C5 N2 C6 179.3(2) . . . . ?
C4 C5 N2 C6 -1.3(2) . . . . ?
O3 C5 N2 C20 -0.5(3) . . . . ?
C4 C5 N2 C20 178.84(18) . . . . ?
C5 N2 C6 O4 -177.7(2) . . . . ?
C20 N2 C6 O4 2.1(3) . . . . ?
C5 N2 C6 C7 1.6(2) . . . . ?
C20 N2 C6 C7 -178.55(19) . . . . ?
C3 C4 C7 C8 -0.1(3) . . . . ?
C5 C4 C7 C8 -177.33(19) . . . . ?
C3 C4 C7 C6 177.75(18) . . . . ?
C5 C4 C7 C6 0.5(2) . . . . ?
O4 C6 C7 C8 -4.5(4) . . . . ?
N2 C6 C7 C8 176.2(2) . . . . ?
O4 C6 C7 C4 178.0(2) . . . . ?
N2 C6 C7 C4 -1.3(2) . . . . ?
C4 C7 C8 C11 -0.8(3) . . . . ?
C6 C7 C8 C11 -178.1(2) . . . . ?
C4 C7 C8 C9 172.8(2) . . . . ?
C6 C7 C8 C9 -4.5(4) . . . . ?
C7 C8 C9 O5 2.5(4) . . . . ?
C11 C8 C9 O5 176.6(2) . . . . ?
C7 C8 C9 N3 -175.9(2) . . . . ?
C11 C8 C9 N3 -1.7(2) . . . . ?
O5 C9 N3 C10 -176.9(2) . . . . ?
C8 C9 N3 C10 1.5(2) . . . . ?
O5 C9 N3 C27 0.2(4) . . . . ?
C8 C9 N3 C27 178.6(2) . . . . ?
C9 N3 C10 O6 176.5(2) . . . . ?
C27 N3 C10 O6 -0.6(4) . . . . ?
C9 N3 C10 C11 -0.7(2) . . . . ?
C27 N3 C10 C11 -177.8(2) . . . . ?
C7 C8 C11 C12 0.6(3) . . . . ?
C9 C8 C11 C12 -174.34(19) . . . . ?
C7 C8 C11 C10 176.25(19) . . . . ?
C9 C8 C11 C10 1.3(2) . . . . ?
O6 C10 C11 C12 -2.6(4) . . . . ?
N3 C10 C11 C12 174.5(2) . . . . ?
O6 C10 C11 C8 -177.5(2) . . . . ?
N3 C10 C11 C8 -0.4(2) . . . . ?
C8 C11 C12 C3 0.5(3) . . . . ?
C10 C11 C12 C3 -173.9(2) . . . . ?
C8 C11 C12 C1 175.9(2) . . . . ?
C10 C11 C12 C1 1.6(4) . . . . ?
C4 C3 C12 C11 -1.4(3) . . . . ?
C2 C3 C12 C11 175.85(18) . . . . ?
C4 C3 C12 C1 -177.86(18) . . . . ?
C2 C3 C12 C1 -0.6(2) . . . . ?
O1 C1 C12 C11 6.3(4) . . . . ?
N1 C1 C12 C11 -173.8(2) . . . . ?
O1 C1 C12 C3 -177.9(2) . . . . ?
N1 C1 C12 C3 2.1(2) . . . . ?
C2 N1 C13 C14 -81.8(3) . . . . ?
C1 N1 C13 C14 96.1(2) . . . . ?
N1 C13 C14 C15 -80.3(3) . . . . ?
N1 C13 C14 C19 97.5(3) . . . . ?
C19 C14 C15 C16 -0.7(4) . . . . ?
C13 C14 C15 C16 177.0(2) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 F1 -179.9(3) . . . . ?
C15 C16 C17 C18 1.8(5) . . . . ?
F1 C17 C18 C19 -179.8(3) . . . . ?
C16 C17 C18 C19 -1.5(5) . . . . ?
C17 C18 C19 C14 0.1(5) . . . . ?
C15 C14 C19 C18 0.9(4) . . . . ?
C13 C14 C19 C18 -176.8(3) . . . . ?
C5 N2 C20 C21 68.9(3) . . . . ?
C6 N2 C20 C21 -111.0(2) . . . . ?
N2 C20 C21 C22 -117.3(2) . . . . ?
N2 C20 C21 C26 62.0(3) . . . . ?
C26 C21 C22 C23 0.7(4) . . . . ?
C20 C21 C22 C23 -179.9(2) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 F2 -179.4(2) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
F2 C24 C25 C26 -180.0(2) . . . . ?
C23 C24 C25 C26 0.8(4) . . . . ?
C24 C25 C26 C21 -0.7(4) . . . . ?
C22 C21 C26 C25 -0.1(4) . . . . ?
C20 C21 C26 C25 -179.5(2) . . . . ?
C10 N3 C27 C28B -105.7(8) . . . . ?
C9 N3 C27 C28B 77.6(8) . . . . ?
C10 N3 C27 C28C -103.8(4) . . . . ?
C9 N3 C27 C28C 79.5(4) . . . . ?
C10 N3 C27 C28A -107.9(5) . . . . ?
C9 N3 C27 C28A 75.4(5) . . . . ?
C28B C27 C28A C29A 74(3) . . . . ?
N3 C27 C28A C29A -114.7(8) . . . . ?
C28C C27 C28A C29A 111(6) . . . . ?
C28B C27 C28A C33A -111(4) . . . . ?
N3 C27 C28A C33A 60.5(11) . . . . ?
C28C C27 C28A C33A -74(6) . . . . ?
C33A C28A C29A C30A 11.1(13) . . . . ?
C27 C28A C29A C30A -173.6(10) . . . . ?
C28A C29A C30A C31A -11.0(13) . . . . ?
C29A C30A C31A F3A -176.8(9) . . . . ?
C29A C30A C31A C32A 7.6(14) . . . . ?
F3A C31A C32A C33A 179.8(9) . . . . ?
C30A C31A C32A C33A -4.6(14) . . . . ?
C31A C32A C33A C28A 4.8(14) . . . . ?
C29A C28A C33A C32A -8.0(14) . . . . ?
C27 C28A C33A C32A 176.8(7) . . . . ?
N3 C27 C28B C29B -78.9(12) . . . . ?
C28C C27 C28B C29B -90(5) . . . . ?
C28A C27 C28B C29B -69(3) . . . . ?
N3 C27 C28B C33B 100.9(11) . . . . ?
C28C C27 C28B C33B 89(5) . . . . ?
C28A C27 C28B C33B 111(4) . . . . ?
C27 C28B C29B C30B 179.9(18) . . . . ?
C33B C28B C29B C30B 0.0 . . . . ?
C28B C29B C30B C31B 0.0 . . . . ?
C29B C30B C31B F3B 175.2(19) . . . . ?
C29B C30B C31B C32B 0.0 . . . . ?
F3B C31B C32B C33B -175.2(19) . . . . ?
C30B C31B C32B C33B 0.0 . . . . ?
C31B C32B C33B C28B 0.0 . . . . ?
C27 C28B C33B C32B -179.9(16) . . . . ?
C29B C28B C33B C32B 0.0 . . . . ?
C28B C27 C28C C29C 67(5) . . . . ?
N3 C27 C28C C29C -102.3(4) . . . . ?
C28A C27 C28C C29C -55(6) . . . . ?
C28B C27 C28C C33C -114(5) . . . . ?
N3 C27 C28C C33C 76.2(6) . . . . ?
C28A C27 C28C C33C 123(6) . . . . ?
C33C C28C C29C C30C 0.0 . . . . ?
C27 C28C C29C C30C 178.5(6) . . . . ?
C28C C29C C30C C31C 0.0 . . . . ?
C29C C30C C31C F3C 176.6(6) . . . . ?
C29C C30C C31C C32C 0.0 . . . . ?
F3C C31C C32C C33C -176.6(6) . . . . ?
C30C C31C C32C C33C 0.0 . . . . ?
C31C C32C C33C C28C 0.0 . . . . ?
C29C C28C C33C C32C 0.0 . . . . ?
C27 C28C C33C C32C -178.5(6) . . . . ?
C92A O90A C90A O91A 3.1(11) . . . . ?
C92A O90A C90A C91A -178.3(7) . . . . ?
C90A O90A C92A C93A -162.7(7) . . . . ?
C92B O90B C90B O91B -3.6(15) . . . . ?
C92B O90B C90B C91B -178.1(8) . . . . ?
C90B O90B C92B C93B -88.6(10) . . . . ?
C92C O90C C90C O91C 1.4(15) . . . . ?
C92C O90C C90C C91C -174.0(8) . . . . ?
C90C O90C C92C C93C 86.9(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.069


#===END

#==============================================================================

#     End of CIF

#==============================================================================
