# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11
_database_code_depnum_ccdc_archive 'CCDC 1815552'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_audit_creation_date             2017-10-09
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C26 H20 N2'
_chemical_formula_moiety         'C26 H20 N2'
_chemical_formula_weight         360.46
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.9592(4)
_cell_length_b                   9.9148(5)
_cell_length_c                   27.7881(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1917.35(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16669
_cell_measurement_theta_min      4.71
_cell_measurement_theta_max      67.95
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760.00
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            23723
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_theta_max         67.934
_diffrn_reflns_theta_min         4.736
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3382
_reflns_number_gt                3292
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.958

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0882
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3382
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0546P)²+0.2689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0414(2) 0.37604(17) 0.12698(6) 0.0325(4) Uani 1 1 d . . . . .
N11 N 0.5258(2) 0.3803(2) 0.15963(6) 0.0414(4) Uani 1 1 d . . . . .
C2 C 0.2254(3) 0.37909(19) 0.10149(7) 0.0312(4) Uani 1 1 d . . . . .
H2 H 0.2321 0.4678 0.0845 0.037 Uiso 1 1 calc R U . . .
C3 C 0.2342(3) 0.27067(19) 0.06304(6) 0.0291(4) Uani 1 1 d . . . . .
C4 C 0.2515(3) 0.1365(2) 0.07592(6) 0.0285(4) Uani 1 1 d . . . . .
C5 C 0.2726(3) 0.10231(18) 0.12799(6) 0.0275(4) Uani 1 1 d . . . . .
C6 C 0.1347(3) 0.15080(19) 0.15943(7) 0.0303(4) Uani 1 1 d . . . . .
C7 C -0.0234(3) 0.2385(2) 0.13982(7) 0.0340(4) Uani 1 1 d . . . . .
H7A H -0.0782 0.1949 0.1109 0.041 Uiso 1 1 calc R U . . .
H7B H -0.1268 0.2453 0.1641 0.041 Uiso 1 1 calc R U . . .
C8 C 0.0354(3) 0.4688(2) 0.16817(8) 0.0395(5) Uani 1 1 d . . . . .
H8A H 0.1300 0.4392 0.1926 0.047 Uiso 1 1 calc R U . . .
H8B H -0.0937 0.4653 0.1830 0.047 Uiso 1 1 calc R U . . .
C9 C 0.0790(4) 0.6107(2) 0.15371(9) 0.0486(6) Uani 1 1 d . . . . .
H9 H 0.0062 0.6491 0.1282 0.058 Uiso 1 1 calc R U . . .
C10 C 0.2106(4) 0.6851(3) 0.17395(9) 0.0570(7) Uani 1 1 d . . . . .
H10A H 0.2857 0.6497 0.1995 0.068 Uiso 1 1 calc R U . . .
H10B H 0.2315 0.7748 0.1631 0.068 Uiso 1 1 calc R U . . .
C11 C 0.3966(3) 0.3729(2) 0.13443(7) 0.0315(4) Uani 1 1 d . . . . .
C12 C 0.2144(3) 0.3084(2) 0.01422(7) 0.0330(4) Uani 1 1 d . . . . .
H12 H 0.2042 0.4011 0.0059 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2097(3) 0.2132(2) -0.02098(7) 0.0337(4) Uani 1 1 d . . . . .
H13 H 0.2008 0.2403 -0.0537 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2178(3) 0.0748(2) -0.00951(6) 0.0334(4) Uani 1 1 d . . . . .
C15 C 0.2009(3) -0.0264(2) -0.04532(7) 0.0417(5) Uani 1 1 d . . . . .
H15 H 0.1936 -0.0007 -0.0782 0.050 Uiso 1 1 calc R U . . .
C16 C 0.1949(4) -0.1586(2) -0.03356(8) 0.0493(6) Uani 1 1 d . . . . .
H16 H 0.1824 -0.2248 -0.0581 0.059 Uiso 1 1 calc R U . . .
C17 C 0.2074(4) -0.1986(2) 0.01508(8) 0.0463(5) Uani 1 1 d . . . . .
H17 H 0.2003 -0.2916 0.0232 0.056 Uiso 1 1 calc R U . . .
C18 C 0.2294(3) -0.1048(2) 0.05046(7) 0.0370(5) Uani 1 1 d . . . . .
H18 H 0.2406 -0.1334 0.0830 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2359(3) 0.03504(19) 0.03955(6) 0.0299(4) Uani 1 1 d . . . . .
C20 C 0.4366(3) 0.03144(18) 0.14584(6) 0.0280(4) Uani 1 1 d . . . . .
C21 C 0.5919(3) -0.01063(19) 0.11639(7) 0.0321(4) Uani 1 1 d . . . . .
H21 H 0.5883 0.0074 0.0828 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7462(3) -0.0763(2) 0.13535(8) 0.0392(5) Uani 1 1 d . . . . .
H22 H 0.8497 -0.1020 0.1150 0.047 Uiso 1 1 calc R U . . .
C23 C 0.7538(3) -0.1066(2) 0.18485(8) 0.0440(5) Uani 1 1 d . . . . .
H23 H 0.8601 -0.1550 0.1976 0.053 Uiso 1 1 calc R U . . .
C24 C 0.6088(3) -0.0665(2) 0.21432(7) 0.0414(5) Uani 1 1 d . . . . .
H24 H 0.6148 -0.0874 0.2477 0.050 Uiso 1 1 calc R U . . .
C25 C 0.4492(3) 0.0058(2) 0.19625(7) 0.0328(4) Uani 1 1 d . . . . .
C26 C 0.3024(3) 0.0538(2) 0.22700(7) 0.0385(5) Uani 1 1 d . . . . .
H26 H 0.3098 0.0362 0.2605 0.046 Uiso 1 1 calc R U . . .
C27 C 0.1516(3) 0.1245(2) 0.20940(7) 0.0359(5) Uani 1 1 d . . . . .
H27 H 0.0558 0.1570 0.2308 0.043 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.464(2) . ?
N1 C8 1.469(3) . ?
N1 C7 1.480(3) . ?
N11 C11 1.142(3) . ?
C2 C11 1.503(3) . ?
C2 C3 1.517(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.383(3) . ?
C3 C12 1.414(2) . ?
C4 C19 1.430(3) . ?
C4 C5 1.493(2) . ?
C5 C6 1.384(3) . ?
C5 C20 1.429(3) . ?
C6 C27 1.418(3) . ?
C6 C7 1.504(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.494(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.304(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C12 C13 1.359(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.410(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.418(3) . ?
C14 C19 1.425(3) . ?
C15 C16 1.352(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.411(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.362(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.420(3) . ?
C18 H18 0.9500 . ?
C20 C21 1.419(3) . ?
C20 C25 1.426(2) . ?
C21 C22 1.362(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.409(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.359(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.414(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.414(3) . ?
C26 C27 1.353(3) . ?
C26 H26 0.9500 . ?
C27 H27 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 N1 C8 112.89(15) . . ?
C2 N1 C7 113.72(15) . . ?
C8 N1 C7 112.38(16) . . ?
N1 C2 C11 113.42(15) . . ?
N1 C2 C3 111.18(15) . . ?
C11 C2 C3 111.59(16) . . ?
N1 C2 H2 106.7 . . ?
C11 C2 H2 106.7 . . ?
C3 C2 H2 106.7 . . ?
C4 C3 C12 120.74(18) . . ?
C4 C3 C2 120.20(16) . . ?
C12 C3 C2 118.99(17) . . ?
C3 C4 C19 119.15(16) . . ?
C3 C4 C5 118.52(16) . . ?
C19 C4 C5 122.21(17) . . ?
C6 C5 C20 120.35(16) . . ?
C6 C5 C4 117.69(16) . . ?
C20 C5 C4 121.77(16) . . ?
C5 C6 C27 119.79(18) . . ?
C5 C6 C7 118.63(16) . . ?
C27 C6 C7 121.46(17) . . ?
N1 C7 C6 113.40(16) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C9 111.99(18) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 124.0(2) . . ?
C10 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
N11 C11 C2 173.9(2) . . ?
C13 C12 C3 120.62(19) . . ?
C13 C12 H12 119.7 . . ?
C3 C12 H12 119.7 . . ?
C12 C13 C14 120.79(17) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 121.77(18) . . ?
C13 C14 C19 119.29(18) . . ?
C15 C14 C19 118.89(19) . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.07(19) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C14 118.14(17) . . ?
C18 C19 C4 122.56(17) . . ?
C14 C19 C4 119.24(18) . . ?
C21 C20 C25 117.86(17) . . ?
C21 C20 C5 123.56(16) . . ?
C25 C20 C5 118.54(17) . . ?
C22 C21 C20 121.21(17) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 121.16(19) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 121.56(18) . . ?
C26 C25 C20 119.26(18) . . ?
C24 C25 C20 119.18(19) . . ?
C27 C26 C25 121.07(17) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C6 120.91(18) . . ?
C26 C27 H27 119.5 . . ?
C6 C27 H27 119.5 . . ?

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
C8 N1 C2 C11 46.6(2) . . . . ?
C7 N1 C2 C11 -82.9(2) . . . . ?
C8 N1 C2 C3 173.33(16) . . . . ?
C7 N1 C2 C3 43.8(2) . . . . ?
N1 C2 C3 C4 -71.9(2) . . . . ?
C11 C2 C3 C4 55.9(2) . . . . ?
N1 C2 C3 C12 104.88(19) . . . . ?
C11 C2 C3 C12 -127.40(18) . . . . ?
C12 C3 C4 C19 -4.2(3) . . . . ?
C2 C3 C4 C19 172.45(16) . . . . ?
C12 C3 C4 C5 179.82(17) . . . . ?
C2 C3 C4 C5 -3.5(3) . . . . ?
C3 C4 C5 C6 54.4(2) . . . . ?
C19 C4 C5 C6 -121.41(19) . . . . ?
C3 C4 C5 C20 -120.66(19) . . . . ?
C19 C4 C5 C20 63.5(2) . . . . ?
C20 C5 C6 C27 -3.0(3) . . . . ?
C4 C5 C6 C27 -178.10(18) . . . . ?
C20 C5 C6 C7 172.99(17) . . . . ?
C4 C5 C6 C7 -2.1(3) . . . . ?
C2 N1 C7 C6 43.2(2) . . . . ?
C8 N1 C7 C6 -86.58(19) . . . . ?
C5 C6 C7 N1 -73.1(2) . . . . ?
C27 C6 C7 N1 102.8(2) . . . . ?
C2 N1 C8 C9 56.4(2) . . . . ?
C7 N1 C8 C9 -173.34(18) . . . . ?
N1 C8 C9 C10 -126.9(3) . . . . ?
C4 C3 C12 C13 0.8(3) . . . . ?
C2 C3 C12 C13 -175.96(17) . . . . ?
C3 C12 C13 C14 2.2(3) . . . . ?
C12 C13 C14 C15 175.94(18) . . . . ?
C12 C13 C14 C19 -1.6(3) . . . . ?
C13 C14 C15 C16 -175.2(2) . . . . ?
C19 C14 C15 C16 2.4(3) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C17 C18 C19 C14 0.3(3) . . . . ?
C17 C18 C19 C4 177.5(2) . . . . ?
C13 C14 C19 C18 175.42(19) . . . . ?
C15 C14 C19 C18 -2.2(3) . . . . ?
C13 C14 C19 C4 -1.9(3) . . . . ?
C15 C14 C19 C4 -179.50(18) . . . . ?
C3 C4 C19 C18 -172.43(18) . . . . ?
C5 C4 C19 C18 3.3(3) . . . . ?
C3 C4 C19 C14 4.8(3) . . . . ?
C5 C4 C19 C14 -179.45(17) . . . . ?
C6 C5 C20 C21 -174.19(18) . . . . ?
C4 C5 C20 C21 0.7(3) . . . . ?
C6 C5 C20 C25 3.3(3) . . . . ?
C4 C5 C20 C25 178.23(17) . . . . ?
C25 C20 C21 C22 1.6(3) . . . . ?
C5 C20 C21 C22 179.10(18) . . . . ?
C20 C21 C22 C23 1.2(3) . . . . ?
C21 C22 C23 C24 -2.0(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 -176.8(2) . . . . ?
C23 C24 C25 C20 2.9(3) . . . . ?
C21 C20 C25 C26 176.12(18) . . . . ?
C5 C20 C25 C26 -1.5(3) . . . . ?
C21 C20 C25 C24 -3.6(3) . . . . ?
C5 C20 C25 C24 178.77(17) . . . . ?
C24 C25 C26 C27 179.1(2) . . . . ?
C20 C25 C26 C27 -0.6(3) . . . . ?
C25 C26 C27 C6 1.0(3) . . . . ?
C5 C6 C27 C26 0.8(3) . . . . ?
C7 C6 C27 C26 -175.04(18) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the 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_-27
_database_code_depnum_ccdc_archive 'CCDC 1815554'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_audit_creation_date             2015-10-25
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C19 H18 F3 N O4'
_chemical_formula_moiety         'C19 H18 F3 N O4'
_chemical_formula_weight         381.35
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.5475(15)
_cell_length_b                   20.671(3)
_cell_length_c                   24.988(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5448.1(14)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    2532
_cell_measurement_theta_min      25.60
_cell_measurement_theta_max      76.30
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2376.00
_exptl_absorpt_coefficient_mu    1.016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_T_max  0.980

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            17111
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_theta_max         68.229
_diffrn_reflns_theta_min         3.538
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             9104
_reflns_number_gt                6168
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1921
_refine_ls_wR_factor_gt          0.1662
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         9104
_refine_ls_number_parameters     946
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1220P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.006
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1933 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(14)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9813(5) 0.2943(2) 0.8549(2) 0.0728(14) Uani 1 1 d . . . . .
F2 F 0.7842(5) 0.2834(3) 0.8739(2) 0.0827(16) Uani 1 1 d . . . . .
F3 F 0.9216(5) 0.2334(2) 0.91999(19) 0.0719(15) Uani 1 1 d . . . . .
F4 F 0.7782(13) 0.3447(4) 0.3098(4) 0.174(5) Uani 1 1 d . . . . .
F5 F 0.6498(6) 0.3966(5) 0.3614(2) 0.125(3) Uani 1 1 d . . . . .
F6 F 0.8414(6) 0.4183(4) 0.3623(3) 0.121(3) Uani 1 1 d . . . . .
F7 F -0.0389(7) 0.0939(4) 0.3122(3) 0.110(2) Uani 1 1 d . . . . .
F8 F -0.0113(9) 0.1145(3) 0.3909(3) 0.128(3) Uani 1 1 d . . . . .
F9 F -0.1969(6) 0.0994(3) 0.3657(5) 0.165(5) Uani 1 1 d . . . . .
O8 O 0.2734(5) 0.1203(2) 0.8501(2) 0.0469(12) Uani 1 1 d . . . . .
O9 O 0.2190(4) 0.2182(2) 0.8201(2) 0.0450(12) Uani 1 1 d D . . . .
O28 O 0.1044(5) 0.4050(3) 0.2448(2) 0.0515(13) Uani 1 1 d . . . . .
O29 O 0.0659(5) 0.4850(2) 0.3020(2) 0.0456(12) Uani 1 1 d D . . . .
O48 O 0.5639(5) -0.0035(2) 0.3224(2) 0.0501(12) Uani 1 1 d . . . . .
O49 O 0.6026(4) 0.0066(2) 0.4099(2) 0.0454(11) Uani 1 1 d D . . . .
O61 O 0.7817(5) 0.1707(3) 0.8235(2) 0.0549(13) Uani 1 1 d . . . . .
O62 O 0.9911(5) 0.1740(3) 0.8164(2) 0.0618(15) Uani 1 1 d . . . . .
O63 O 0.8276(5) 0.4816(3) 0.2721(2) 0.0548(14) Uani 1 1 d . . . . .
O64 O 0.6253(5) 0.4508(3) 0.2629(2) 0.0501(13) Uani 1 1 d . . . . .
O65 O -0.1604(5) -0.0195(3) 0.3936(3) 0.0572(14) Uani 1 1 d . . . . .
O66 O 0.0396(4) -0.0147(2) 0.3643(2) 0.0498(13) Uani 1 1 d . . . . .
N1 N 0.5237(5) 0.1481(3) 0.8552(2) 0.0386(13) Uani 1 1 d D . . . .
N21 N 0.3569(6) 0.4055(3) 0.2621(3) 0.0439(14) Uani 1 1 d D . . . .
N41 N 0.3077(5) 0.0105(3) 0.3338(2) 0.0396(13) Uani 1 1 d D . . . .
C2 C 0.4367(7) 0.1956(3) 0.8269(3) 0.0394(15) Uani 1 1 d . . . . .
C3 C 0.4662(7) 0.2649(3) 0.8419(3) 0.0395(16) Uani 1 1 d . . . . .
C4 C 0.4395(6) 0.2889(3) 0.8925(3) 0.0374(16) Uani 1 1 d . . . . .
C5 C 0.3821(6) 0.2441(3) 0.9325(3) 0.0345(14) Uani 1 1 d . . . . .
C6 C 0.4410(6) 0.1849(3) 0.9423(3) 0.0364(15) Uani 1 1 d . . . . .
C7 C 0.5564(7) 0.1667(4) 0.9111(3) 0.0388(17) Uani 1 1 d . . . . .
C8 C 0.3001(6) 0.1736(3) 0.8348(3) 0.0363(15) Uani 1 1 d . . . . .
C10 C 0.5209(8) 0.3042(4) 0.8030(4) 0.053(2) Uani 1 1 d . . . . .
C11 C 0.5533(9) 0.3676(4) 0.8152(4) 0.065(2) Uani 1 1 d . . . . .
C12 C 0.5300(9) 0.3903(4) 0.8665(4) 0.059(2) Uani 1 1 d . . . . .
C13 C 0.4750(7) 0.3526(3) 0.9056(3) 0.0438(17) Uani 1 1 d . . . . .
C14 C 0.4530(9) 0.3825(4) 0.9600(4) 0.0499(19) Uani 1 1 d . . . . .
C15 C 0.2659(7) 0.2577(3) 0.9580(3) 0.0399(16) Uani 1 1 d . . . . .
C16 C 0.2184(8) 0.2129(4) 0.9945(3) 0.0493(19) Uani 1 1 d . . . . .
C17 C 0.2816(8) 0.1559(4) 1.0052(3) 0.0485(18) Uani 1 1 d . . . . .
C18 C 0.3929(8) 0.1415(4) 0.9788(3) 0.0438(18) Uani 1 1 d . . . . .
C19 C 0.1901(8) 0.3173(4) 0.9459(4) 0.053(2) Uani 1 1 d . . . . .
C22 C 0.2811(7) 0.4616(3) 0.2832(3) 0.0392(16) Uani 1 1 d . . . . .
C23 C 0.3280(6) 0.4809(3) 0.3373(3) 0.0358(15) Uani 1 1 d . . . . .
C24 C 0.3068(6) 0.4412(3) 0.3816(3) 0.0360(16) Uani 1 1 d . . . . .
C25 C 0.2273(6) 0.3820(3) 0.3740(3) 0.0366(15) Uani 1 1 d . . . . .
C26 C 0.2663(6) 0.3373(3) 0.3355(3) 0.0384(16) Uani 1 1 d . . . . .
C27 C 0.3821(7) 0.3524(3) 0.3022(3) 0.0430(17) Uani 1 1 d . . . . .
C28 C 0.1389(7) 0.4457(3) 0.2750(3) 0.0404(16) Uani 1 1 d . . . . .
C30 C 0.4008(8) 0.5365(4) 0.3433(4) 0.052(2) Uani 1 1 d . . . . .
C31 C 0.4529(9) 0.5513(4) 0.3927(4) 0.057(2) Uani 1 1 d . . . . .
C32 C 0.4348(8) 0.5113(4) 0.4351(4) 0.059(2) Uani 1 1 d . . . . .
C33 C 0.3653(8) 0.4558(4) 0.4317(3) 0.0475(18) Uani 1 1 d . . . . .
C34 C 0.3587(11) 0.4118(5) 0.4793(4) 0.062(2) Uani 1 1 d . . . . .
C35 C 0.1157(6) 0.3711(3) 0.4033(3) 0.0404(16) Uani 1 1 d . . . . .
C36 C 0.0506(8) 0.3145(4) 0.3940(4) 0.054(2) Uani 1 1 d . . . . .
C37 C 0.0904(8) 0.2700(4) 0.3571(4) 0.057(2) Uani 1 1 d . . . . .
C38 C 0.1971(8) 0.2816(4) 0.3268(4) 0.0498(19) Uani 1 1 d . . . . .
C39 C 0.0629(8) 0.4225(4) 0.4403(4) 0.0528(19) Uani 1 1 d . . . . .
C42 C 0.3869(6) 0.0027(3) 0.3832(3) 0.0377(15) Uani 1 1 d . . . . .
C43 C 0.3465(6) 0.0485(3) 0.4269(3) 0.0343(14) Uani 1 1 d . . . . .
C44 C 0.3672(6) 0.1150(3) 0.4226(3) 0.0341(14) Uani 1 1 d . . . . .
C45 C 0.4351(6) 0.1398(3) 0.3744(3) 0.0317(14) Uani 1 1 d . . . . .
C46 C 0.3884(6) 0.1226(3) 0.3241(3) 0.0349(14) Uani 1 1 d . . . . .
C47 C 0.2751(7) 0.0790(3) 0.3198(3) 0.0409(16) Uani 1 1 d . . . . .
C48 C 0.5286(6) 0.0026(3) 0.3678(3) 0.0381(15) Uani 1 1 d . . . . .
C50 C 0.2799(7) 0.0231(4) 0.4697(3) 0.0439(17) Uani 1 1 d . . . . .
C51 C 0.2317(7) 0.0640(5) 0.5085(3) 0.052(2) Uani 1 1 d . . . . .
C52 C 0.2485(7) 0.1283(5) 0.5042(3) 0.049(2) Uani 1 1 d . . . . .
C53 C 0.3154(6) 0.1560(3) 0.4617(3) 0.0411(16) Uani 1 1 d . . . . .
C54 C 0.3228(10) 0.2284(4) 0.4587(4) 0.056(2) Uani 1 1 d . . . . .
C55 C 0.5461(7) 0.1771(3) 0.3775(3) 0.0398(16) Uani 1 1 d . . . . .
C56 C 0.6001(8) 0.1999(3) 0.3302(3) 0.0454(18) Uani 1 1 d . . . . .
C57 C 0.5503(8) 0.1849(4) 0.2813(4) 0.0510(19) Uani 1 1 d . . . . .
C58 C 0.4449(8) 0.1460(3) 0.2779(3) 0.0454(17) Uani 1 1 d . . . . .
C59 C 0.6093(9) 0.1926(5) 0.4291(4) 0.052(2) Uani 1 1 d . . . . .
C61 C 0.8879(7) 0.1912(4) 0.8341(3) 0.0493(19) Uani 1 1 d . . . . .
C62 C 0.8915(8) 0.2519(4) 0.8702(4) 0.056(2) Uani 1 1 d . . . . .
C63 C 0.7320(7) 0.4498(4) 0.2838(3) 0.0431(16) Uani 1 1 d . . . . .
C64 C 0.7492(8) 0.4011(6) 0.3290(4) 0.074(3) Uani 1 1 d . . . . .
C65 C -0.0677(7) 0.0077(3) 0.3731(3) 0.0456(17) Uani 1 1 d . . . . .
C66 C -0.0851(8) 0.0772(4) 0.3582(5) 0.067(3) Uani 1 1 d . . . . .
H1A H 0.478(6) 0.107(2) 0.857(3) 0.044(19) Uiso 1 1 d D . . . .
H1B H 0.609(6) 0.142(7) 0.841(6) 0.15(5) Uiso 1 1 d D . . . .
H2 H 0.451(6) 0.191(3) 0.786(3) 0.025(15) Uiso 1 1 d . . . . .
H9 H 0.139(4) 0.195(4) 0.815(4) 0.08(3) Uiso 1 1 d D . . . .
H29 H -0.019(3) 0.470(3) 0.292(3) 0.030(17) Uiso 1 1 d D . . . .
H49 H 0.695(2) 0.001(8) 0.411(7) 0.16(6) Uiso 1 1 d D . . . .
H7A H 0.591(8) 0.136(4) 0.928(3) 0.05(2) Uiso 1 1 d . . . . .
H7B H 0.611(8) 0.193(4) 0.913(3) 0.04(2) Uiso 1 1 d . . . . .
H10 H 0.530(9) 0.284(4) 0.764(4) 0.07(3) Uiso 1 1 d . . . . .
H11 H 0.590(7) 0.398(4) 0.785(3) 0.05(2) Uiso 1 1 d . . . . .
H12 H 0.548(7) 0.431(4) 0.872(3) 0.039(18) Uiso 1 1 d . . . . .
H14A H 0.388(6) 0.417(3) 0.960(3) 0.030(16) Uiso 1 1 d . . . . .
H14B H 0.452(7) 0.352(4) 0.987(3) 0.04(2) Uiso 1 1 d . . . . .
H14C H 0.525(7) 0.409(4) 0.965(3) 0.038(18) Uiso 1 1 d . . . . .
H16 H 0.148(7) 0.220(3) 1.012(3) 0.033(18) Uiso 1 1 d . . . . .
H17 H 0.247(9) 0.123(5) 1.029(4) 0.08(3) Uiso 1 1 d . . . . .
H18 H 0.432(6) 0.109(3) 0.986(2) 0.020(16) Uiso 1 1 d . . . . .
H19A H 0.201(8) 0.356(4) 0.968(4) 0.06(2) Uiso 1 1 d . . . . .
H19B H 0.204(10) 0.333(5) 0.911(5) 0.08(3) Uiso 1 1 d . . . . .
H19C H 0.100(9) 0.303(4) 0.944(3) 0.05(2) Uiso 1 1 d . . . . .
H21A H 0.315(9) 0.386(4) 0.232(3) 0.08(3) Uiso 1 1 d D . . . .
H21B H 0.438(5) 0.427(4) 0.260(3) 0.07(3) Uiso 1 1 d D . . . .
H22 H 0.295(7) 0.492(4) 0.257(3) 0.04(2) Uiso 1 1 d . . . . .
H27A H 0.399(6) 0.316(3) 0.284(3) 0.033(17) Uiso 1 1 d . . . . .
H27B H 0.455(7) 0.370(3) 0.324(3) 0.034(17) Uiso 1 1 d . . . . .
H30 H 0.405(6) 0.561(3) 0.311(3) 0.020(15) Uiso 1 1 d . . . . .
H31 H 0.497(7) 0.579(4) 0.399(3) 0.04(2) Uiso 1 1 d . . . . .
H32 H 0.466(8) 0.518(4) 0.467(3) 0.05(2) Uiso 1 1 d . . . . .
H34A H 0.331(13) 0.440(7) 0.502(6) 0.12(5) Uiso 1 1 d . . . . .
H34B H 0.318(8) 0.368(5) 0.475(4) 0.06(3) Uiso 1 1 d . . . . .
H34C H 0.432(11) 0.401(5) 0.502(4) 0.09(3) Uiso 1 1 d . . . . .
H36 H -0.012(7) 0.310(3) 0.408(3) 0.03(2) Uiso 1 1 d . . . . .
H37 H 0.067(11) 0.239(5) 0.349(4) 0.07(3) Uiso 1 1 d . . . . .
H38 H 0.222(9) 0.252(5) 0.301(4) 0.07(3) Uiso 1 1 d . . . . .
H39A H 0.105(12) 0.422(6) 0.477(5) 0.11(4) Uiso 1 1 d . . . . .
H39B H 0.30(2) 0.446(10) 0.411(8) 0.18(9) Uiso 1 1 d . . . . .
H39C H 0.072(8) 0.462(4) 0.421(4) 0.06(3) Uiso 1 1 d . . . . .
H41A H 0.328(9) -0.013(4) 0.301(2) 0.08(3) Uiso 1 1 d D . . . .
H41B H 0.232(4) -0.015(3) 0.340(3) 0.034(17) Uiso 1 1 d D . . . .
H42 H 0.373(8) -0.040(4) 0.389(3) 0.06(2) Uiso 1 1 d . . . . .
H47A H 0.238(7) 0.077(3) 0.288(3) 0.04(2) Uiso 1 1 d . . . . .
H47B H 0.205(8) 0.094(4) 0.338(3) 0.05(2) Uiso 1 1 d . . . . .
H50 H 0.265(7) -0.017(4) 0.468(3) 0.04(2) Uiso 1 1 d . . . . .
H51 H 0.192(7) 0.054(3) 0.538(3) 0.036(19) Uiso 1 1 d . . . . .
H52 H 0.220(6) 0.152(3) 0.526(3) 0.023(17) Uiso 1 1 d . . . . .
H54A H 0.400(10) 0.250(5) 0.484(4) 0.08(3) Uiso 1 1 d . . . . .
H54B H 0.340(8) 0.250(4) 0.420(4) 0.06(2) Uiso 1 1 d . . . . .
H54C H 0.261(9) 0.249(4) 0.471(4) 0.06(3) Uiso 1 1 d . . . . .
H56 H 0.667(7) 0.224(3) 0.333(3) 0.032(18) Uiso 1 1 d . . . . .
H57 H 0.591(7) 0.203(3) 0.250(3) 0.036(18) Uiso 1 1 d . . . . .
H58 H 0.416(7) 0.127(3) 0.247(3) 0.033(18) Uiso 1 1 d . . . . .
H59A H 0.580(10) 0.242(5) 0.444(4) 0.09(3) Uiso 1 1 d . . . . .
H59B H 0.602(9) 0.166(5) 0.457(4) 0.07(3) Uiso 1 1 d . . . . .
H59C H 0.681(11) 0.203(5) 0.428(4) 0.07(3) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C62 1.345(10) . ?
F2 C62 1.309(9) . ?
F3 C62 1.340(10) . ?
F4 C64 1.298(14) . ?
F5 C64 1.328(12) . ?
F6 C64 1.328(10) . ?
F7 C66 1.294(11) . ?
F8 C66 1.367(13) . ?
F9 C66 1.278(10) . ?
O8 C8 1.200(8) . ?
O9 C8 1.310(8) . ?
O9 H9 0.980(7) . ?
O28 C28 1.187(8) . ?
O29 C28 1.307(8) . ?
O29 H29 0.980(7) . ?
O48 C48 1.200(8) . ?
O49 C48 1.312(8) . ?
O49 H49 0.980(7) . ?
O61 C61 1.226(9) . ?
O62 C61 1.227(9) . ?
O63 C63 1.237(9) . ?
O64 C63 1.241(9) . ?
O65 C65 1.239(9) . ?
O66 C65 1.243(8) . ?
N1 C7 1.489(10) . ?
N1 C2 1.519(9) . ?
N1 H1A 0.98(3) . ?
N1 H1B 0.98(3) . ?
N21 C22 1.505(9) . ?
N21 C27 1.508(10) . ?
N21 H21A 0.97(3) . ?
N21 H21B 0.97(3) . ?
N41 C47 1.499(9) . ?
N41 C42 1.499(9) . ?
N41 H41A 0.97(3) . ?
N41 H41B 0.97(3) . ?
C2 C3 1.512(10) . ?
C2 C8 1.524(10) . ?
C2 H2 1.04(7) . ?
C3 C4 1.386(10) . ?
C3 C10 1.394(11) . ?
C4 C13 1.409(10) . ?
C4 C5 1.493(10) . ?
C5 C6 1.393(9) . ?
C5 C15 1.410(10) . ?
C6 C18 1.376(10) . ?
C6 C7 1.493(10) . ?
C7 H7A 0.85(9) . ?
C7 H7B 0.80(9) . ?
C10 C11 1.389(12) . ?
C10 H10 1.07(10) . ?
C11 C12 1.386(13) . ?
C11 H11 1.06(8) . ?
C12 C13 1.377(12) . ?
C12 H12 0.88(7) . ?
C13 C14 1.510(11) . ?
C14 H14A 0.99(7) . ?
C14 H14B 0.93(8) . ?
C14 H14C 0.95(8) . ?
C15 C16 1.392(11) . ?
C15 C19 1.500(11) . ?
C16 C17 1.378(12) . ?
C16 H16 0.88(8) . ?
C17 C18 1.379(12) . ?
C17 H17 0.98(11) . ?
C18 H18 0.82(6) . ?
C19 H19A 0.99(9) . ?
C19 H19B 0.94(12) . ?
C19 H19C 0.99(9) . ?
C22 C23 1.492(10) . ?
C22 C28 1.550(11) . ?
C22 H22 0.91(8) . ?
C23 C30 1.391(10) . ?
C23 C24 1.395(10) . ?
C24 C33 1.429(13) . ?
C24 C25 1.496(9) . ?
C24 H39B 0.7(2) . ?
C25 C26 1.395(10) . ?
C25 C35 1.405(10) . ?
C26 C38 1.382(10) . ?
C26 C27 1.511(11) . ?
C27 H27A 0.90(7) . ?
C27 H27B 1.02(7) . ?
C30 C31 1.386(13) . ?
C30 H30 0.95(7) . ?
C31 C32 1.358(14) . ?
C31 H31 0.75(8) . ?
C32 C33 1.364(12) . ?
C32 H32 0.87(8) . ?
C33 C34 1.497(13) . ?
C33 H39B 0.9(2) . ?
C34 H34A 0.86(16) . ?
C34 H34B 1.01(9) . ?
C34 H34C 0.99(12) . ?
C35 C36 1.377(11) . ?
C35 C39 1.515(11) . ?
C36 C37 1.369(14) . ?
C36 H36 0.76(7) . ?
C37 C38 1.377(13) . ?
C37 H37 0.71(11) . ?
C38 H38 0.92(10) . ?
C39 H39A 1.02(12) . ?
C39 H39C 0.95(9) . ?
C42 C43 1.506(10) . ?
C42 C48 1.544(10) . ?
C42 H42 0.91(9) . ?
C43 C50 1.383(10) . ?
C43 C44 1.396(9) . ?
C44 C53 1.404(10) . ?
C44 C45 1.493(10) . ?
C45 C46 1.394(9) . ?
C45 C55 1.404(9) . ?
C46 C58 1.386(10) . ?
C46 C47 1.500(10) . ?
C47 H47A 0.89(8) . ?
C47 H47B 0.92(9) . ?
C50 C51 1.382(12) . ?
C50 H50 0.85(8) . ?
C51 C52 1.345(13) . ?
C51 H51 0.87(8) . ?
C52 C53 1.399(11) . ?
C52 H52 0.79(7) . ?
C53 C54 1.500(11) . ?
C54 H54A 1.13(11) . ?
C54 H54B 1.08(9) . ?
C54 H54C 0.83(10) . ?
C55 C56 1.395(11) . ?
C55 C59 1.487(12) . ?
C56 C57 1.366(12) . ?
C56 H56 0.87(7) . ?
C57 C58 1.375(12) . ?
C57 H57 0.96(7) . ?
C58 H58 0.92(7) . ?
C59 H59A 1.13(11) . ?
C59 H59B 0.89(11) . ?
C59 H59C 0.78(11) . ?
C61 C62 1.546(11) . ?
C63 C64 1.525(12) . ?
C65 C66 1.497(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O9 H9 105(5) . . ?
C28 O29 H29 102(4) . . ?
C48 O49 H49 128(10) . . ?
C7 N1 C2 114.2(5) . . ?
C7 N1 H1A 107(4) . . ?
C2 N1 H1A 106(4) . . ?
C7 N1 H1B 100(9) . . ?
C2 N1 H1B 118(9) . . ?
H1A N1 H1B 111(10) . . ?
C22 N21 C27 114.9(6) . . ?
C22 N21 H21A 111(6) . . ?
C27 N21 H21A 107(6) . . ?
C22 N21 H21B 98(5) . . ?
C27 N21 H21B 103(5) . . ?
H21A N21 H21B 124(8) . . ?
C47 N41 C42 114.9(5) . . ?
C47 N41 H41A 109(6) . . ?
C42 N41 H41A 121(6) . . ?
C47 N41 H41B 111(4) . . ?
C42 N41 H41B 106(4) . . ?
H41A N41 H41B 93(7) . . ?
C3 C2 N1 111.9(6) . . ?
C3 C2 C8 116.4(6) . . ?
N1 C2 C8 108.6(5) . . ?
C3 C2 H2 108(3) . . ?
N1 C2 H2 108(3) . . ?
C8 C2 H2 104(3) . . ?
C4 C3 C10 120.7(6) . . ?
C4 C3 C2 121.6(6) . . ?
C10 C3 C2 117.7(7) . . ?
C3 C4 C13 119.6(6) . . ?
C3 C4 C5 118.1(6) . . ?
C13 C4 C5 122.1(7) . . ?
C6 C5 C15 118.9(6) . . ?
C6 C5 C4 118.8(6) . . ?
C15 C5 C4 122.1(6) . . ?
C18 C6 C5 121.6(7) . . ?
C18 C6 C7 118.8(6) . . ?
C5 C6 C7 119.5(6) . . ?
C6 C7 N1 111.5(6) . . ?
C6 C7 H7A 106(6) . . ?
N1 C7 H7A 112(6) . . ?
C6 C7 H7B 113(6) . . ?
N1 C7 H7B 114(6) . . ?
H7A C7 H7B 100(7) . . ?
O8 C8 O9 125.6(6) . . ?
O8 C8 C2 122.5(6) . . ?
O9 C8 C2 111.8(5) . . ?
C11 C10 C3 119.9(8) . . ?
C11 C10 H10 124(5) . . ?
C3 C10 H10 116(5) . . ?
C12 C11 C10 118.6(8) . . ?
C12 C11 H11 121(4) . . ?
C10 C11 H11 120(4) . . ?
C13 C12 C11 122.7(8) . . ?
C13 C12 H12 121(5) . . ?
C11 C12 H12 116(5) . . ?
C12 C13 C4 118.4(7) . . ?
C12 C13 C14 118.2(7) . . ?
C4 C13 C14 123.5(7) . . ?
C13 C14 H14A 113(4) . . ?
C13 C14 H14B 112(5) . . ?
H14A C14 H14B 119(6) . . ?
C13 C14 H14C 104(4) . . ?
H14A C14 H14C 98(6) . . ?
H14B C14 H14C 108(7) . . ?
C16 C15 C5 118.3(7) . . ?
C16 C15 C19 119.2(7) . . ?
C5 C15 C19 122.4(7) . . ?
C17 C16 C15 121.5(8) . . ?
C17 C16 H16 117(4) . . ?
C15 C16 H16 122(5) . . ?
C18 C17 C16 120.2(7) . . ?
C18 C17 H17 118(6) . . ?
C16 C17 H17 122(6) . . ?
C6 C18 C17 119.3(7) . . ?
C6 C18 H18 120(4) . . ?
C17 C18 H18 121(4) . . ?
C15 C19 H19A 120(5) . . ?
C15 C19 H19B 112(6) . . ?
H19A C19 H19B 103(8) . . ?
C15 C19 H19C 106(5) . . ?
H19A C19 H19C 113(7) . . ?
H19B C19 H19C 101(8) . . ?
C23 C22 N21 110.3(6) . . ?
C23 C22 C28 119.9(6) . . ?
N21 C22 C28 107.7(5) . . ?
C23 C22 H22 114(5) . . ?
N21 C22 H22 102(5) . . ?
C28 C22 H22 102(5) . . ?
C30 C23 C24 119.2(7) . . ?
C30 C23 C22 120.1(7) . . ?
C24 C23 C22 120.5(6) . . ?
C23 C24 C33 120.2(6) . . ?
C23 C24 C25 118.0(7) . . ?
C33 C24 C25 121.7(7) . . ?
C23 C24 H39B 135(10) . . ?
C33 C24 H39B 30(10) . . ?
C25 C24 H39B 102(10) . . ?
C26 C25 C35 120.0(6) . . ?
C26 C25 C24 117.6(6) . . ?
C35 C25 C24 122.4(6) . . ?
C38 C26 C25 120.4(7) . . ?
C38 C26 C27 120.8(7) . . ?
C25 C26 C27 118.8(6) . . ?
C26 C27 N21 112.0(6) . . ?
C26 C27 H27A 105(4) . . ?
N21 C27 H27A 108(4) . . ?
C26 C27 H27B 113(4) . . ?
N21 C27 H27B 104(4) . . ?
H27A C27 H27B 115(6) . . ?
O28 C28 O29 126.1(7) . . ?
O28 C28 C22 122.1(6) . . ?
O29 C28 C22 111.7(6) . . ?
C31 C30 C23 119.8(8) . . ?
C31 C30 H30 128(4) . . ?
C23 C30 H30 112(4) . . ?
C32 C31 C30 120.4(8) . . ?
C32 C31 H31 112(6) . . ?
C30 C31 H31 127(6) . . ?
C31 C32 C33 122.6(9) . . ?
C31 C32 H32 125(5) . . ?
C33 C32 H32 113(5) . . ?
C32 C33 C24 117.6(8) . . ?
C32 C33 C34 119.1(8) . . ?
C24 C33 C34 123.2(7) . . ?
C32 C33 H39B 130(10) . . ?
C24 C33 H39B 26(10) . . ?
C34 C33 H39B 108(10) . . ?
C33 C34 H34A 97(10) . . ?
C33 C34 H34B 118(5) . . ?
H34A C34 H34B 123(10) . . ?
C33 C34 H34C 124(6) . . ?
H34A C34 H34C 92(10) . . ?
H34B C34 H34C 102(8) . . ?
C36 C35 C25 117.8(7) . . ?
C36 C35 C39 121.1(7) . . ?
C25 C35 C39 120.9(6) . . ?
C37 C36 C35 122.2(8) . . ?
C37 C36 H36 120(5) . . ?
C35 C36 H36 118(6) . . ?
C36 C37 C38 120.3(8) . . ?
C36 C37 H37 134(9) . . ?
C38 C37 H37 106(9) . . ?
C37 C38 C26 119.3(9) . . ?
C37 C38 H38 120(6) . . ?
C26 C38 H38 120(6) . . ?
C35 C39 H39A 112(7) . . ?
C35 C39 H39C 105(5) . . ?
H39A C39 H39C 115(9) . . ?
N41 C42 C43 111.8(5) . . ?
N41 C42 C48 109.5(6) . . ?
C43 C42 C48 117.1(6) . . ?
N41 C42 H42 99(5) . . ?
C43 C42 H42 116(5) . . ?
C48 C42 H42 102(5) . . ?
C50 C43 C44 120.8(6) . . ?
C50 C43 C42 117.8(6) . . ?
C44 C43 C42 121.2(6) . . ?
C43 C44 C53 118.7(6) . . ?
C43 C44 C45 118.4(6) . . ?
C53 C44 C45 122.7(6) . . ?
C46 C45 C55 119.0(6) . . ?
C46 C45 C44 118.0(5) . . ?
C55 C45 C44 122.9(6) . . ?
C58 C46 C45 120.6(6) . . ?
C58 C46 C47 119.5(7) . . ?
C45 C46 C47 119.9(6) . . ?
N41 C47 C46 111.6(6) . . ?
N41 C47 H47A 106(5) . . ?
C46 C47 H47A 116(5) . . ?
N41 C47 H47B 112(5) . . ?
C46 C47 H47B 114(5) . . ?
H47A C47 H47B 96(7) . . ?
O48 C48 O49 125.4(6) . . ?
O48 C48 C42 122.4(6) . . ?
O49 C48 C42 112.1(6) . . ?
C43 C50 C51 119.8(8) . . ?
C43 C50 H50 116(5) . . ?
C51 C50 H50 124(5) . . ?
C52 C51 C50 120.0(8) . . ?
C52 C51 H51 112(5) . . ?
C50 C51 H51 128(5) . . ?
C51 C52 C53 122.1(8) . . ?
C51 C52 H52 120(5) . . ?
C53 C52 H52 118(5) . . ?
C52 C53 C44 118.5(7) . . ?
C52 C53 C54 118.2(7) . . ?
C44 C53 C54 123.2(7) . . ?
C53 C54 H54A 114(5) . . ?
C53 C54 H54B 117(4) . . ?
H54A C54 H54B 103(7) . . ?
C53 C54 H54C 117(6) . . ?
H54A C54 H54C 99(8) . . ?
H54B C54 H54C 104(8) . . ?
C56 C55 C45 118.7(7) . . ?
C56 C55 C59 118.6(7) . . ?
C45 C55 C59 122.7(7) . . ?
C57 C56 C55 121.6(7) . . ?
C57 C56 H56 121(5) . . ?
C55 C56 H56 117(5) . . ?
C56 C57 C58 119.9(8) . . ?
C56 C57 H57 117(4) . . ?
C58 C57 H57 123(4) . . ?
C57 C58 C46 120.1(8) . . ?
C57 C58 H58 125(4) . . ?
C46 C58 H58 114(4) . . ?
C55 C59 H59A 111(5) . . ?
C55 C59 H59B 120(6) . . ?
H59A C59 H59B 107(8) . . ?
C55 C59 H59C 117(8) . . ?
H59A C59 H59C 92(9) . . ?
H59B C59 H59C 107(10) . . ?
O62 C61 O61 129.2(7) . . ?
O62 C61 C62 115.1(6) . . ?
O61 C61 C62 115.4(7) . . ?
F2 C62 F1 107.8(7) . . ?
F2 C62 F3 106.3(7) . . ?
F1 C62 F3 106.4(7) . . ?
F2 C62 C61 115.1(7) . . ?
F1 C62 C61 112.3(7) . . ?
F3 C62 C61 108.4(7) . . ?
O63 C63 O64 129.1(7) . . ?
O63 C63 C64 115.4(6) . . ?
O64 C63 C64 115.5(7) . . ?
F4 C64 F5 110.5(10) . . ?
F4 C64 F6 107.4(10) . . ?
F5 C64 F6 102.4(9) . . ?
F4 C64 C63 110.3(9) . . ?
F5 C64 C63 113.9(8) . . ?
F6 C64 C63 112.0(8) . . ?
O65 C65 O66 128.5(7) . . ?
O65 C65 C66 116.3(6) . . ?
O66 C65 C66 115.1(7) . . ?
F9 C66 F7 112.5(9) . . ?
F9 C66 F8 103.6(9) . . ?
F7 C66 F8 99.5(7) . . ?
F9 C66 C65 114.9(7) . . ?
F7 C66 C65 115.5(8) . . ?
F8 C66 C65 108.8(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
C7 N1 C2 C3 36.9(8) . . . . ?
C7 N1 C2 C8 -92.9(7) . . . . ?
N1 C2 C3 C4 -70.4(8) . . . . ?
C8 C2 C3 C4 55.1(9) . . . . ?
N1 C2 C3 C10 109.9(7) . . . . ?
C8 C2 C3 C10 -124.5(8) . . . . ?
C10 C3 C4 C13 -3.8(10) . . . . ?
C2 C3 C4 C13 176.5(6) . . . . ?
C10 C3 C4 C5 -179.4(7) . . . . ?
C2 C3 C4 C5 0.9(9) . . . . ?
C3 C4 C5 C6 52.3(9) . . . . ?
C13 C4 C5 C6 -123.2(7) . . . . ?
C3 C4 C5 C15 -123.2(7) . . . . ?
C13 C4 C5 C15 61.3(9) . . . . ?
C15 C5 C6 C18 -4.4(10) . . . . ?
C4 C5 C6 C18 179.9(6) . . . . ?
C15 C5 C6 C7 173.3(6) . . . . ?
C4 C5 C6 C7 -2.4(9) . . . . ?
C18 C6 C7 N1 103.6(8) . . . . ?
C5 C6 C7 N1 -74.2(8) . . . . ?
C2 N1 C7 C6 48.5(8) . . . . ?
C3 C2 C8 O8 -142.6(7) . . . . ?
N1 C2 C8 O8 -15.4(9) . . . . ?
C3 C2 C8 O9 41.2(9) . . . . ?
N1 C2 C8 O9 168.4(6) . . . . ?
C4 C3 C10 C11 2.3(12) . . . . ?
C2 C3 C10 C11 -178.0(8) . . . . ?
C3 C10 C11 C12 -0.1(13) . . . . ?
C10 C11 C12 C13 -0.5(14) . . . . ?
C11 C12 C13 C4 -1.0(12) . . . . ?
C11 C12 C13 C14 -179.5(8) . . . . ?
C3 C4 C13 C12 3.1(10) . . . . ?
C5 C4 C13 C12 178.5(7) . . . . ?
C3 C4 C13 C14 -178.4(7) . . . . ?
C5 C4 C13 C14 -3.0(10) . . . . ?
C6 C5 C15 C16 3.8(10) . . . . ?
C4 C5 C15 C16 179.3(6) . . . . ?
C6 C5 C15 C19 -174.1(7) . . . . ?
C4 C5 C15 C19 1.4(11) . . . . ?
C5 C15 C16 C17 -0.9(11) . . . . ?
C19 C15 C16 C17 177.1(7) . . . . ?
C15 C16 C17 C18 -1.5(12) . . . . ?
C5 C6 C18 C17 2.1(10) . . . . ?
C7 C6 C18 C17 -175.6(6) . . . . ?
C16 C17 C18 C6 0.9(11) . . . . ?
C27 N21 C22 C23 44.1(8) . . . . ?
C27 N21 C22 C28 -88.4(7) . . . . ?
N21 C22 C23 C30 104.8(7) . . . . ?
C28 C22 C23 C30 -129.2(7) . . . . ?
N21 C22 C23 C24 -70.8(8) . . . . ?
C28 C22 C23 C24 55.2(9) . . . . ?
C30 C23 C24 C33 -3.6(10) . . . . ?
C22 C23 C24 C33 172.1(6) . . . . ?
C30 C23 C24 C25 179.5(6) . . . . ?
C22 C23 C24 C25 -4.8(9) . . . . ?
C23 C24 C25 C26 57.2(8) . . . . ?
C33 C24 C25 C26 -119.6(7) . . . . ?
C23 C24 C25 C35 -121.6(7) . . . . ?
C33 C24 C25 C35 61.5(9) . . . . ?
C35 C25 C26 C38 -1.3(10) . . . . ?
C24 C25 C26 C38 179.8(6) . . . . ?
C35 C25 C26 C27 176.2(6) . . . . ?
C24 C25 C26 C27 -2.7(9) . . . . ?
C38 C26 C27 N21 105.8(7) . . . . ?
C25 C26 C27 N21 -71.7(8) . . . . ?
C22 N21 C27 C26 42.4(8) . . . . ?
C23 C22 C28 O28 -144.9(7) . . . . ?
N21 C22 C28 O28 -17.7(9) . . . . ?
C23 C22 C28 O29 39.4(9) . . . . ?
N21 C22 C28 O29 166.6(5) . . . . ?
C24 C23 C30 C31 1.1(11) . . . . ?
C22 C23 C30 C31 -174.6(7) . . . . ?
C23 C30 C31 C32 0.9(12) . . . . ?
C30 C31 C32 C33 -0.3(13) . . . . ?
C31 C32 C33 C24 -2.1(12) . . . . ?
C31 C32 C33 C34 175.1(9) . . . . ?
C23 C24 C33 C32 4.0(10) . . . . ?
C25 C24 C33 C32 -179.2(7) . . . . ?
C23 C24 C33 C34 -173.1(8) . . . . ?
C25 C24 C33 C34 3.7(11) . . . . ?
C26 C25 C35 C36 2.2(10) . . . . ?
C24 C25 C35 C36 -178.9(7) . . . . ?
C26 C25 C35 C39 -172.5(7) . . . . ?
C24 C25 C35 C39 6.4(10) . . . . ?
C25 C35 C36 C37 -0.8(11) . . . . ?
C39 C35 C36 C37 173.9(8) . . . . ?
C35 C36 C37 C38 -1.6(13) . . . . ?
C36 C37 C38 C26 2.6(12) . . . . ?
C25 C26 C38 C37 -1.1(11) . . . . ?
C27 C26 C38 C37 -178.5(7) . . . . ?
C47 N41 C42 C43 39.9(8) . . . . ?
C47 N41 C42 C48 -91.6(7) . . . . ?
N41 C42 C43 C50 105.6(7) . . . . ?
C48 C42 C43 C50 -126.8(7) . . . . ?
N41 C42 C43 C44 -69.7(8) . . . . ?
C48 C42 C43 C44 57.8(9) . . . . ?
C50 C43 C44 C53 -2.1(9) . . . . ?
C42 C43 C44 C53 173.1(6) . . . . ?
C50 C43 C44 C45 -177.5(6) . . . . ?
C42 C43 C44 C45 -2.3(9) . . . . ?
C43 C44 C45 C46 53.7(8) . . . . ?
C53 C44 C45 C46 -121.5(7) . . . . ?
C43 C44 C45 C55 -123.6(7) . . . . ?
C53 C44 C45 C55 61.3(9) . . . . ?
C55 C45 C46 C58 -4.8(9) . . . . ?
C44 C45 C46 C58 177.9(6) . . . . ?
C55 C45 C46 C47 175.8(6) . . . . ?
C44 C45 C46 C47 -1.6(8) . . . . ?
C42 N41 C47 C46 45.3(8) . . . . ?
C58 C46 C47 N41 107.5(8) . . . . ?
C45 C46 C47 N41 -73.1(8) . . . . ?
N41 C42 C48 O48 -13.8(9) . . . . ?
C43 C42 C48 O48 -142.4(6) . . . . ?
N41 C42 C48 O49 169.6(5) . . . . ?
C43 C42 C48 O49 40.9(8) . . . . ?
C44 C43 C50 C51 0.8(10) . . . . ?
C42 C43 C50 C51 -174.5(7) . . . . ?
C43 C50 C51 C52 0.6(11) . . . . ?
C50 C51 C52 C53 -0.8(12) . . . . ?
C51 C52 C53 C44 -0.5(11) . . . . ?
C51 C52 C53 C54 176.6(8) . . . . ?
C43 C44 C53 C52 1.9(9) . . . . ?
C45 C44 C53 C52 177.1(6) . . . . ?
C43 C44 C53 C54 -175.0(7) . . . . ?
C45 C44 C53 C54 0.1(11) . . . . ?
C46 C45 C55 C56 4.9(9) . . . . ?
C44 C45 C55 C56 -177.8(6) . . . . ?
C46 C45 C55 C59 -174.2(7) . . . . ?
C44 C45 C55 C59 3.0(10) . . . . ?
C45 C55 C56 C57 -2.3(10) . . . . ?
C59 C55 C56 C57 176.9(7) . . . . ?
C55 C56 C57 C58 -0.6(11) . . . . ?
C56 C57 C58 C46 0.8(11) . . . . ?
C45 C46 C58 C57 1.9(10) . . . . ?
C47 C46 C58 C57 -178.7(6) . . . . ?
O62 C61 C62 F2 157.3(8) . . . . ?
O61 C61 C62 F2 -16.7(11) . . . . ?
O62 C61 C62 F1 33.5(10) . . . . ?
O61 C61 C62 F1 -140.5(8) . . . . ?
O62 C61 C62 F3 -83.8(9) . . . . ?
O61 C61 C62 F3 102.2(9) . . . . ?
O63 C63 C64 F4 -93.2(10) . . . . ?
O64 C63 C64 F4 84.9(11) . . . . ?
O63 C63 C64 F5 141.9(8) . . . . ?
O64 C63 C64 F5 -40.0(12) . . . . ?
O63 C63 C64 F6 26.3(12) . . . . ?
O64 C63 C64 F6 -155.6(8) . . . . ?
O65 C65 C66 F9 -3.8(14) . . . . ?
O66 C65 C66 F9 177.8(10) . . . . ?
O65 C65 C66 F7 -137.3(9) . . . . ?
O66 C65 C66 F7 44.2(12) . . . . ?
O65 C65 C66 F8 111.8(8) . . . . ?
O66 C65 C66 F8 -66.6(10) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the 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_+28
_database_code_depnum_ccdc_archive 'CCDC 1815553'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C31 H31 N O2'
_chemical_formula_moiety         'C31 H31 N O2'
_chemical_formula_weight         449.59
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.0982(7)
_cell_length_b                   16.4309(13)
_cell_length_c                   10.0674(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 113.247(2)
_cell_angle_gamma                90.0000
_cell_volume                     1230.82(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6307
_cell_measurement_theta_min      4.76
_cell_measurement_theta_max      67.36
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480.00
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            14497
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_theta_max         67.709
_diffrn_reflns_theta_min         4.781
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3976
_reflns_number_gt                3554
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.816
_reflns_Friedel_fraction_full    0.817

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0942
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3976
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0176P)²+0.9893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(16)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O12 O 0.2870(4) -0.06977(18) 0.6298(3) 0.0317(7) Uani 1 1 d . . . . .
O13 O 0.2330(3) 0.05513(17) 0.5278(3) 0.0226(6) Uani 1 1 d . . . . .
N1 N -0.0329(4) 0.0055(2) 0.8633(4) 0.0246(8) Uani 1 1 d . . . . .
C2 C 0.1173(5) -0.0107(3) 0.8179(4) 0.0225(9) Uani 1 1 d . . . . .
H2 H 0.1290 -0.0712 0.8174 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2989(5) 0.0207(3) 0.9259(4) 0.0210(9) Uani 1 1 d . . . . .
C4 C 0.3349(5) 0.1031(2) 0.9558(4) 0.0208(9) Uani 1 1 d . . . . .
C5 C 0.1947(5) 0.1629(2) 0.8680(4) 0.0199(9) Uani 1 1 d . . . . .
C6 C 0.0217(5) 0.1524(3) 0.8589(4) 0.0227(10) Uani 1 1 d . . . . .
C7 C -0.0191(6) 0.0833(3) 0.9390(5) 0.0278(10) Uani 1 1 d . . . . .
H7A H 0.0771 0.0794 1.0371 0.033 Uiso 1 1 calc R U . . .
H7B H -0.1337 0.0943 0.9492 0.033 Uiso 1 1 calc R U . . .
C8 C -0.0569(6) -0.0614(3) 0.9514(5) 0.0308(11) Uani 1 1 d . . . . .
H8A H -0.1398 -0.0435 0.9964 0.037 Uiso 1 1 calc R U . . .
H8B H 0.0604 -0.0743 1.0301 0.037 Uiso 1 1 calc R U . . .
C9 C -0.1303(8) -0.1361(3) 0.8642(5) 0.0429(14) Uani 1 1 d . . . . .
H9 H -0.2467 -0.1331 0.7888 0.051 Uiso 1 1 calc R U . . .
C10 C -0.0450(9) -0.2053(4) 0.8846(6) 0.0592(17) Uani 1 1 d . . . . .
H10A H 0.0717 -0.2103 0.9590 0.071 Uiso 1 1 calc R U . . .
H10B H -0.0995 -0.2507 0.8250 0.071 Uiso 1 1 calc R U . . .
C11 C 0.0656(5) 0.0165(3) 0.6604(4) 0.0215(9) Uani 1 1 d . . . . .
H11A H -0.0489 -0.0098 0.5982 0.026 Uiso 1 1 calc R U . . .
H11B H 0.0469 0.0762 0.6536 0.026 Uiso 1 1 calc R U . . .
C12 C 0.2088(5) -0.0054(3) 0.6068(4) 0.0203(9) Uani 1 1 d . . . . .
C13 C 0.3645(5) 0.0480(3) 0.4596(4) 0.0267(10) Uani 1 1 d . . . . .
C14 C 0.3462(8) 0.1295(3) 0.3864(6) 0.0477(14) Uani 1 1 d . . . . .
H14A H 0.4284 0.1320 0.3366 0.057 Uiso 1 1 calc R U . . .
H14B H 0.2224 0.1365 0.3160 0.057 Uiso 1 1 calc R U . . .
H14C H 0.3760 0.1728 0.4590 0.057 Uiso 1 1 calc R U . . .
C15 C 0.5514(6) 0.0364(3) 0.5748(5) 0.0426(13) Uani 1 1 d . . . . .
H15A H 0.6377 0.0318 0.5291 0.051 Uiso 1 1 calc R U . . .
H15B H 0.5828 0.0833 0.6403 0.051 Uiso 1 1 calc R U . . .
H15C H 0.5547 -0.0132 0.6297 0.051 Uiso 1 1 calc R U . . .
C16 C 0.3103(7) -0.0204(3) 0.3507(5) 0.0369(12) Uani 1 1 d . . . . .
H16A H 0.3977 -0.0249 0.3060 0.044 Uiso 1 1 calc R U . . .
H16B H 0.3071 -0.0717 0.3996 0.044 Uiso 1 1 calc R U . . .
H16C H 0.1910 -0.0092 0.2760 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4308(6) -0.0372(3) 1.0028(4) 0.0241(10) Uani 1 1 d . . . . .
H17 H 0.4067 -0.0933 0.9805 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5913(6) -0.0153(3) 1.1078(4) 0.0260(10) Uani 1 1 d . . . . .
H18 H 0.6791 -0.0556 1.1547 0.031 Uiso 1 1 calc R U . . .
C19 C 0.6272(5) 0.0676(3) 1.1469(4) 0.0241(10) Uani 1 1 d . . . . .
C20 C 0.7878(6) 0.0925(3) 1.2623(4) 0.0308(11) Uani 1 1 d . . . . .
H20 H 0.8768 0.0530 1.3112 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8170(6) 0.1717(3) 1.3043(5) 0.0345(12) Uani 1 1 d . . . . .
H21 H 0.9257 0.1871 1.3814 0.041 Uiso 1 1 calc R U . . .
C22 C 0.6857(6) 0.2310(3) 1.2333(5) 0.0322(11) Uani 1 1 d . . . . .
H22 H 0.7047 0.2860 1.2646 0.039 Uiso 1 1 calc R U . . .
C23 C 0.5317(6) 0.2095(3) 1.1202(4) 0.0246(10) Uani 1 1 d . . . . .
H23 H 0.4453 0.2503 1.0728 0.030 Uiso 1 1 calc R U . . .
C24 C 0.4970(5) 0.1275(3) 1.0710(4) 0.0217(9) Uani 1 1 d . . . . .
C25 C 0.2310(5) 0.2232(2) 0.7798(4) 0.0210(9) Uani 1 1 d . . . . .
C26 C 0.4026(5) 0.2360(3) 0.7775(4) 0.0225(9) Uani 1 1 d . . . . .
H26 H 0.5018 0.2049 0.8398 0.027 Uiso 1 1 calc R U . . .
C27 C 0.4284(6) 0.2921(3) 0.6878(5) 0.0285(10) Uani 1 1 d . . . . .
H27 H 0.5457 0.3003 0.6902 0.034 Uiso 1 1 calc R U . . .
C28 C 0.2840(6) 0.3378(3) 0.5919(5) 0.0297(10) Uani 1 1 d . . . . .
H28 H 0.3034 0.3761 0.5288 0.036 Uiso 1 1 calc R U . . .
C29 C 0.1163(6) 0.3271(3) 0.5896(5) 0.0281(10) Uani 1 1 d . . . . .
H29 H 0.0189 0.3582 0.5246 0.034 Uiso 1 1 calc R U . . .
C30 C 0.0855(6) 0.2704(2) 0.6828(5) 0.0261(10) Uani 1 1 d . . . . .
C31 C -0.0903(6) 0.2578(3) 0.6791(5) 0.0301(11) Uani 1 1 d . . . . .
H31 H -0.1880 0.2893 0.6159 0.036 Uiso 1 1 calc R U . . .
C32 C -0.1186(6) 0.2009(3) 0.7654(5) 0.0276(10) Uani 1 1 d . . . . .
H32 H -0.2364 0.1938 0.7625 0.033 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O12 C12 1.208(5) . ?
O13 C12 1.336(5) . ?
O13 C13 1.482(5) . ?
N1 C7 1.468(5) . ?
N1 C8 1.473(5) . ?
N1 C2 1.483(5) . ?
C2 C3 1.532(6) . ?
C2 C11 1.538(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.392(6) . ?
C3 C17 1.411(6) . ?
C4 C24 1.424(6) . ?
C4 C5 1.498(6) . ?
C5 C6 1.378(6) . ?
C5 C25 1.437(6) . ?
C6 C32 1.404(6) . ?
C6 C7 1.502(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.490(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.303(7) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C12 1.503(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C14 1.507(7) . ?
C13 C16 1.510(6) . ?
C13 C15 1.512(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.361(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.416(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.420(6) . ?
C19 C24 1.424(6) . ?
C20 C21 1.360(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.410(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.362(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.425(6) . ?
C23 H23 0.9500 . ?
C25 C26 1.415(5) . ?
C25 C30 1.426(6) . ?
C26 C27 1.363(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.405(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.360(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.414(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.424(6) . ?
C31 C32 1.356(6) . ?
C31 H31 0.9500 . ?
C32 H32 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 O13 C13 121.2(3) . . ?
C7 N1 C8 109.8(3) . . ?
C7 N1 C2 114.3(3) . . ?
C8 N1 C2 111.8(3) . . ?
N1 C2 C3 113.3(3) . . ?
N1 C2 C11 110.1(3) . . ?
C3 C2 C11 115.4(3) . . ?
N1 C2 H2 105.7 . . ?
C3 C2 H2 105.7 . . ?
C11 C2 H2 105.7 . . ?
C4 C3 C17 119.2(4) . . ?
C4 C3 C2 122.7(4) . . ?
C17 C3 C2 118.0(4) . . ?
C3 C4 C24 119.8(4) . . ?
C3 C4 C5 117.7(4) . . ?
C24 C4 C5 122.4(4) . . ?
C6 C5 C25 119.7(4) . . ?
C6 C5 C4 118.1(4) . . ?
C25 C5 C4 121.7(3) . . ?
C5 C6 C32 120.4(4) . . ?
C5 C6 C7 119.5(4) . . ?
C32 C6 C7 119.9(4) . . ?
N1 C7 C6 111.5(3) . . ?
N1 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 112.1(4) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 124.2(5) . . ?
C10 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C12 C11 C2 111.5(3) . . ?
C12 C11 H11A 109.3 . . ?
C2 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C2 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O12 C12 O13 125.2(4) . . ?
O12 C12 C11 124.2(4) . . ?
O13 C12 C11 110.6(3) . . ?
O13 C13 C14 101.9(3) . . ?
O13 C13 C16 109.8(3) . . ?
C14 C13 C16 111.3(4) . . ?
O13 C13 C15 109.8(3) . . ?
C14 C13 C15 111.2(4) . . ?
C16 C13 C15 112.3(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C3 122.1(4) . . ?
C18 C17 H17 118.9 . . ?
C3 C17 H17 118.9 . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 121.7(4) . . ?
C18 C19 C24 119.2(4) . . ?
C20 C19 C24 119.0(4) . . ?
C21 C20 C19 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 120.0(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 121.7(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C4 C24 C19 119.4(4) . . ?
C4 C24 C23 122.8(4) . . ?
C19 C24 C23 117.7(4) . . ?
C26 C25 C30 117.3(4) . . ?
C26 C25 C5 123.7(4) . . ?
C30 C25 C5 118.9(3) . . ?
C27 C26 C25 121.3(4) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 120.9(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 119.8(4) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.7(4) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C31 121.0(4) . . ?
C29 C30 C25 119.9(4) . . ?
C31 C30 C25 119.1(4) . . ?
C32 C31 C30 120.3(4) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C6 121.6(4) . . ?
C31 C32 H32 119.2 . . ?
C6 C32 H32 119.2 . . ?

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
C7 N1 C2 C3 35.8(5) . . . . ?
C8 N1 C2 C3 -89.6(4) . . . . ?
C7 N1 C2 C11 -95.0(4) . . . . ?
C8 N1 C2 C11 139.5(3) . . . . ?
N1 C2 C3 C4 -65.0(5) . . . . ?
C11 C2 C3 C4 63.2(5) . . . . ?
N1 C2 C3 C17 111.9(4) . . . . ?
C11 C2 C3 C17 -120.0(4) . . . . ?
C17 C3 C4 C24 -5.2(6) . . . . ?
C2 C3 C4 C24 171.5(4) . . . . ?
C17 C3 C4 C5 177.6(3) . . . . ?
C2 C3 C4 C5 -5.6(6) . . . . ?
C3 C4 C5 C6 52.4(5) . . . . ?
C24 C4 C5 C6 -124.6(4) . . . . ?
C3 C4 C5 C25 -119.4(4) . . . . ?
C24 C4 C5 C25 63.5(5) . . . . ?
C25 C5 C6 C32 -0.8(6) . . . . ?
C4 C5 C6 C32 -172.8(4) . . . . ?
C25 C5 C6 C7 173.3(4) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C8 N1 C7 C6 175.0(3) . . . . ?
C2 N1 C7 C6 48.5(5) . . . . ?
C5 C6 C7 N1 -77.9(5) . . . . ?
C32 C6 C7 N1 96.3(4) . . . . ?
C7 N1 C8 C9 161.4(4) . . . . ?
C2 N1 C8 C9 -70.7(5) . . . . ?
N1 C8 C9 C10 116.9(5) . . . . ?
N1 C2 C11 C12 -175.2(3) . . . . ?
C3 C2 C11 C12 55.0(5) . . . . ?
C13 O13 C12 O12 -0.4(6) . . . . ?
C13 O13 C12 C11 -178.7(3) . . . . ?
C2 C11 C12 O12 42.6(5) . . . . ?
C2 C11 C12 O13 -139.0(3) . . . . ?
C12 O13 C13 C14 -179.1(4) . . . . ?
C12 O13 C13 C16 62.9(5) . . . . ?
C12 O13 C13 C15 -61.1(5) . . . . ?
C4 C3 C17 C18 1.5(6) . . . . ?
C2 C3 C17 C18 -175.5(4) . . . . ?
C3 C17 C18 C19 2.6(6) . . . . ?
C17 C18 C19 C20 175.7(4) . . . . ?
C17 C18 C19 C24 -2.8(6) . . . . ?
C18 C19 C20 C21 -176.4(4) . . . . ?
C24 C19 C20 C21 2.1(6) . . . . ?
C19 C20 C21 C22 0.4(7) . . . . ?
C20 C21 C22 C23 -1.8(7) . . . . ?
C21 C22 C23 C24 0.8(6) . . . . ?
C3 C4 C24 C19 5.0(6) . . . . ?
C5 C4 C24 C19 -178.0(4) . . . . ?
C3 C4 C24 C23 -171.3(4) . . . . ?
C5 C4 C24 C23 5.7(6) . . . . ?
C18 C19 C24 C4 -1.0(6) . . . . ?
C20 C19 C24 C4 -179.5(4) . . . . ?
C18 C19 C24 C23 175.5(4) . . . . ?
C20 C19 C24 C23 -3.1(6) . . . . ?
C22 C23 C24 C4 178.0(4) . . . . ?
C22 C23 C24 C19 1.7(6) . . . . ?
C6 C5 C25 C26 -177.3(4) . . . . ?
C4 C5 C25 C26 -5.6(6) . . . . ?
C6 C5 C25 C30 -0.9(6) . . . . ?
C4 C5 C25 C30 170.9(4) . . . . ?
C30 C25 C26 C27 1.0(6) . . . . ?
C5 C25 C26 C27 177.5(4) . . . . ?
C25 C26 C27 C28 -1.5(7) . . . . ?
C26 C27 C28 C29 1.0(7) . . . . ?
C27 C28 C29 C30 0.0(7) . . . . ?
C28 C29 C30 C31 -178.8(4) . . . . ?
C28 C29 C30 C25 -0.5(6) . . . . ?
C26 C25 C30 C29 0.0(6) . . . . ?
C5 C25 C30 C29 -176.7(4) . . . . ?
C26 C25 C30 C31 178.4(4) . . . . ?
C5 C25 C30 C31 1.7(6) . . . . ?
C29 C30 C31 C32 177.5(4) . . . . ?
C25 C30 C31 C32 -0.9(6) . . . . ?
C30 C31 C32 C6 -0.8(7) . . . . ?
C5 C6 C32 C31 1.7(6) . . . . ?
C7 C6 C32 C31 -172.4(4) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the 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_+16
_database_code_depnum_ccdc_archive 'CCDC 1815555'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_audit_creation_date             2015-09-04
_audit_creation_method           'by CrystalStructure 4.1'



_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_moiety         'C24 H19 N O2'
_chemical_formula_weight         353.42
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.6334(16)
_cell_length_b                   14.828(3)
_cell_length_c                   15.793(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1787.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2113
_cell_measurement_theta_min      25.70
_cell_measurement_theta_max      75.60
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744.00
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.936

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            10230
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         4.090
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3125
_reflns_number_gt                3049
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1238
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3125
_refine_ls_number_parameters     249
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0613P)²+0.2300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1158 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, S., Flack, H.D. and Wagner, T. Acta Cryst. B69 (2013) 249-259.).
;
_refine_ls_abs_structure_Flack   -0.08(14)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.8602(3) 0.65858(12) 0.41450(13) 0.0367(5) Uani 1 1 d . . . . .
O9 O 0.9301(2) 0.51140(12) 0.40731(12) 0.0335(5) Uani 1 1 d . . . . .
N1 N 0.5034(3) 0.61884(15) 0.43743(14) 0.0326(5) Uani 1 1 d D . . . .
C2 C 0.6258(3) 0.54915(16) 0.41019(17) 0.0283(6) Uani 1 1 d . . . . .
H2 H 0.5990 0.5372 0.3492 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5926(3) 0.46115(16) 0.45654(17) 0.0267(6) Uani 1 1 d . . . . .
C4 C 0.6377(3) 0.45175(15) 0.54091(16) 0.0253(6) Uani 1 1 d . . . . .
C5 C 0.7258(3) 0.52907(16) 0.58421(16) 0.0260(5) Uani 1 1 d . . . . .
C6 C 0.6439(4) 0.61275(16) 0.58079(16) 0.0279(6) Uani 1 1 d . . . . .
C7 C 0.4773(4) 0.62340(17) 0.52990(17) 0.0320(6) Uani 1 1 d . . . . .
H7A H 0.3940 0.5755 0.5468 0.038 Uiso 1 1 calc R U . . .
H7B H 0.4233 0.6822 0.5441 0.038 Uiso 1 1 calc R U . . .
C8 C 0.8167(4) 0.58001(17) 0.41321(17) 0.0297(6) Uani 1 1 d . . . . .
C9 C 1.1136(4) 0.5368(2) 0.4119(2) 0.0431(7) Uani 1 1 d . . . . .
H9A H 1.1352 0.5695 0.4648 0.052 Uiso 1 1 calc R U . . .
H9B H 1.1429 0.5755 0.3637 0.052 Uiso 1 1 calc R U . . .
H9C H 1.1865 0.4824 0.4104 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5047(4) 0.39057(16) 0.41345(16) 0.0285(6) Uani 1 1 d . . . . .
H10 H 0.4759 0.3978 0.3553 0.034 Uiso 1 1 calc R U . . .
C11 C 0.4607(3) 0.31275(16) 0.45374(17) 0.0291(6) Uani 1 1 d . . . . .
H11 H 0.4029 0.2661 0.4234 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5003(4) 0.30063(16) 0.54050(16) 0.0279(6) Uani 1 1 d . . . . .
C13 C 0.4498(4) 0.22098(17) 0.58442(17) 0.0308(6) Uani 1 1 d . . . . .
H13 H 0.3931 0.1737 0.5545 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4818(4) 0.21153(17) 0.66913(17) 0.0322(6) Uani 1 1 d . . . . .
H14 H 0.4476 0.1580 0.6977 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5657(4) 0.28145(17) 0.71386(17) 0.0309(6) Uani 1 1 d . . . . .
H15 H 0.5865 0.2750 0.7728 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6175(4) 0.35860(16) 0.67340(16) 0.0280(6) Uani 1 1 d . . . . .
H16 H 0.6735 0.4050 0.7049 0.034 Uiso 1 1 calc R U . . .
C17 C 0.5894(3) 0.37067(16) 0.58518(16) 0.0256(6) Uani 1 1 d . . . . .
C18 C 0.8958(3) 0.52115(16) 0.62278(16) 0.0262(6) Uani 1 1 d . . . . .
C19 C 0.9948(4) 0.44001(17) 0.62104(17) 0.0304(6) Uani 1 1 d . . . . .
H19 H 0.9464 0.3880 0.5948 0.036 Uiso 1 1 calc R U . . .
C20 C 1.1590(4) 0.43506(19) 0.65656(17) 0.0340(6) Uani 1 1 d . . . . .
H20 H 1.2223 0.3799 0.6551 0.041 Uiso 1 1 calc R U . . .
C21 C 1.2336(4) 0.5116(2) 0.69512(17) 0.0374(7) Uani 1 1 d . . . . .
H21 H 1.3468 0.5080 0.7199 0.045 Uiso 1 1 calc R U . . .
C22 C 1.1434(4) 0.59097(19) 0.69694(17) 0.0347(6) Uani 1 1 d . . . . .
H22 H 1.1954 0.6425 0.7225 0.042 Uiso 1 1 calc R U . . .
C23 C 0.9728(4) 0.59795(16) 0.66124(16) 0.0286(6) Uani 1 1 d . . . . .
C24 C 0.8799(4) 0.68124(17) 0.66052(17) 0.0322(6) Uani 1 1 d . . . . .
H24 H 0.9279 0.7322 0.6886 0.039 Uiso 1 1 calc R U . . .
C25 C 0.7230(4) 0.68853(16) 0.61994(17) 0.0326(6) Uani 1 1 d . . . . .
H25 H 0.6657 0.7454 0.6179 0.039 Uiso 1 1 calc R U . . .
H1 H 0.557(5) 0.6745(15) 0.417(2) 0.066(11) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O8 C8 1.211(3) . ?
O9 C8 1.339(3) . ?
O9 C9 1.452(3) . ?
N1 C2 1.458(3) . ?
N1 C7 1.475(3) . ?
N1 H1 0.979(7) . ?
C2 C3 1.517(3) . ?
C2 C8 1.528(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.383(4) . ?
C3 C10 1.417(3) . ?
C4 C17 1.439(3) . ?
C4 C5 1.495(3) . ?
C5 C6 1.391(3) . ?
C5 C18 1.438(4) . ?
C6 C25 1.418(4) . ?
C6 C7 1.513(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.360(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.415(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.423(4) . ?
C12 C17 1.428(3) . ?
C13 C14 1.367(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.409(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.421(4) . ?
C16 H16 0.9500 . ?
C18 C23 1.418(3) . ?
C18 C19 1.421(4) . ?
C19 C20 1.376(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.408(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.364(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.423(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.424(4) . ?
C24 C25 1.363(4) . ?
C24 H24 0.9500 . ?
C25 H25 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
C8 O9 C9 115.0(2) . . ?
C2 N1 C7 114.3(2) . . ?
C2 N1 H1 103(2) . . ?
C7 N1 H1 110(2) . . ?
N1 C2 C3 111.1(2) . . ?
N1 C2 C8 112.9(2) . . ?
C3 C2 C8 113.7(2) . . ?
N1 C2 H2 106.1 . . ?
C3 C2 H2 106.1 . . ?
C8 C2 H2 106.1 . . ?
C4 C3 C10 120.4(2) . . ?
C4 C3 C2 120.6(2) . . ?
C10 C3 C2 118.9(2) . . ?
C3 C4 C17 119.2(2) . . ?
C3 C4 C5 118.4(2) . . ?
C17 C4 C5 122.3(2) . . ?
C6 C5 C18 119.7(2) . . ?
C6 C5 C4 117.7(2) . . ?
C18 C5 C4 122.5(2) . . ?
C5 C6 C25 119.9(2) . . ?
C5 C6 C7 119.5(2) . . ?
C25 C6 C7 120.5(2) . . ?
N1 C7 C6 114.1(2) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O8 C8 O9 123.7(3) . . ?
O8 C8 C2 123.3(2) . . ?
O9 C8 C2 112.7(2) . . ?
O9 C9 H9A 109.5 . . ?
O9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O9 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C3 121.3(2) . . ?
C11 C10 H10 119.4 . . ?
C3 C10 H10 119.4 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 C17 119.2(2) . . ?
C13 C12 C17 119.5(2) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.3(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C12 117.7(2) . . ?
C16 C17 C4 122.9(2) . . ?
C12 C17 C4 119.3(2) . . ?
C23 C18 C19 117.9(2) . . ?
C23 C18 C5 119.3(2) . . ?
C19 C18 C5 122.7(2) . . ?
C20 C19 C18 121.5(2) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 121.1(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C18 C23 C24 119.1(2) . . ?
C18 C23 C22 119.4(2) . . ?
C24 C23 C22 121.4(2) . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C6 121.1(2) . . ?
C24 C25 H25 119.4 . . ?
C6 C25 H25 119.4 . . ?

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
C7 N1 C2 C3 44.3(3) . . . . ?
C7 N1 C2 C8 -84.8(3) . . . . ?
N1 C2 C3 C4 -72.9(3) . . . . ?
C8 C2 C3 C4 55.9(3) . . . . ?
N1 C2 C3 C10 103.3(3) . . . . ?
C8 C2 C3 C10 -128.0(3) . . . . ?
C10 C3 C4 C17 -2.0(4) . . . . ?
C2 C3 C4 C17 174.1(2) . . . . ?
C10 C3 C4 C5 -178.3(2) . . . . ?
C2 C3 C4 C5 -2.2(4) . . . . ?
C3 C4 C5 C6 53.8(3) . . . . ?
C17 C4 C5 C6 -122.4(3) . . . . ?
C3 C4 C5 C18 -121.3(3) . . . . ?
C17 C4 C5 C18 62.5(3) . . . . ?
C18 C5 C6 C25 -4.0(4) . . . . ?
C4 C5 C6 C25 -179.2(2) . . . . ?
C18 C5 C6 C7 171.7(2) . . . . ?
C4 C5 C6 C7 -3.6(3) . . . . ?
C2 N1 C7 C6 41.5(3) . . . . ?
C5 C6 C7 N1 -70.6(3) . . . . ?
C25 C6 C7 N1 105.0(3) . . . . ?
C9 O9 C8 O8 6.6(4) . . . . ?
C9 O9 C8 C2 -178.6(2) . . . . ?
N1 C2 C8 O8 -19.5(4) . . . . ?
C3 C2 C8 O8 -147.3(3) . . . . ?
N1 C2 C8 O9 165.6(2) . . . . ?
C3 C2 C8 O9 37.8(3) . . . . ?
C4 C3 C10 C11 0.8(4) . . . . ?
C2 C3 C10 C11 -175.4(2) . . . . ?
C3 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 177.8(2) . . . . ?
C10 C11 C12 C17 -0.9(4) . . . . ?
C11 C12 C13 C14 -177.1(3) . . . . ?
C17 C12 C13 C14 1.5(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C15 C16 C17 C12 1.8(4) . . . . ?
C15 C16 C17 C4 178.3(2) . . . . ?
C11 C12 C17 C16 176.3(2) . . . . ?
C13 C12 C17 C16 -2.4(4) . . . . ?
C11 C12 C17 C4 -0.3(4) . . . . ?
C13 C12 C17 C4 -179.0(2) . . . . ?
C3 C4 C17 C16 -174.6(2) . . . . ?
C5 C4 C17 C16 1.5(4) . . . . ?
C3 C4 C17 C12 1.8(4) . . . . ?
C5 C4 C17 C12 177.9(2) . . . . ?
C6 C5 C18 C23 3.7(4) . . . . ?
C4 C5 C18 C23 178.7(2) . . . . ?
C6 C5 C18 C19 -173.5(2) . . . . ?
C4 C5 C18 C19 1.5(4) . . . . ?
C23 C18 C19 C20 1.0(4) . . . . ?
C5 C18 C19 C20 178.3(2) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C19 C18 C23 C24 177.2(2) . . . . ?
C5 C18 C23 C24 -0.2(4) . . . . ?
C19 C18 C23 C22 -0.6(4) . . . . ?
C5 C18 C23 C22 -177.9(2) . . . . ?
C21 C22 C23 C18 -0.3(4) . . . . ?
C21 C22 C23 C24 -178.0(2) . . . . ?
C18 C23 C24 C25 -3.2(4) . . . . ?
C22 C23 C24 C25 174.5(2) . . . . ?
C23 C24 C25 C6 3.0(4) . . . . ?
C5 C6 C25 C24 0.6(4) . . . . ?
C7 C6 C25 C24 -175.0(2) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


