# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1478152'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_audit_creation_date             2016-04-25
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C29 H28 N2 O'
_chemical_formula_moiety         'C29 H28 N2 O'
_chemical_formula_weight         420.55
_chemical_melting_point          ?
_chemical_absolute_configuration syn

#==============================================================================
# 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                   8.118(7)
_cell_length_b                   16.336(13)
_cell_length_c                   8.515(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.597(14)
_cell_angle_gamma                90.0000
_cell_volume                     1128.8(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    617
_cell_measurement_theta_min      5.20
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448.00
_exptl_absorpt_coefficient_mu    0.581
_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 XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            11833
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_theta_max         68.181
_diffrn_reflns_theta_min         5.197
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3369
_reflns_number_gt                2564
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_max     0.624
_reflns_Friedel_fraction_full    0.628

#==============================================================================
# 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          0.0882
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1777
_refine_ls_wR_factor_gt          0.1492
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3369
_refine_ls_number_parameters     294
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0751P)²+0.7263P] 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         0.25
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0059(12)
_refine_ls_abs_structure_details 
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   1.1(8)

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
O24 O 0.5690(5) 0.3803(2) -0.0493(5) 0.0471(10) Uani 1 1 d D . . . .
N5 N 0.5530(5) 0.1194(3) 0.2126(5) 0.0341(10) Uani 1 1 d . . . . .
N6 N 0.4162(5) 0.0526(3) 0.0006(5) 0.0342(10) Uani 1 1 d . . . . .
C1 C 0.5456(7) 0.3407(3) 0.3028(6) 0.0372(12) Uani 1 1 d . . . . .
H1 H 0.4966 0.3899 0.2646 0.045 Uiso 1 1 calc R U . . .
C1A C 0.5194(6) 0.2685(3) 0.2191(6) 0.0342(11) Uani 1 1 d . . . . .
C2 C 0.6418(7) 0.3428(4) 0.4413(7) 0.0429(13) Uani 1 1 d . . . . .
H2 H 0.6564 0.3929 0.4969 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7155(7) 0.2722(4) 0.4972(6) 0.0421(13) Uani 1 1 d . . . . .
H3 H 0.7837 0.2737 0.5897 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6900(7) 0.1992(4) 0.4182(6) 0.0389(12) Uani 1 1 d . . . . .
H4 H 0.7414 0.1505 0.4559 0.047 Uiso 1 1 calc R U . . .
C4A C 0.5889(6) 0.1969(3) 0.2831(6) 0.0329(11) Uani 1 1 d . . . . .
C5 C 0.5728(7) 0.0436(3) 0.3043(7) 0.0383(12) Uani 1 1 d . . . . .
H5A H 0.4883 0.0037 0.2677 0.046 Uiso 1 1 calc R U . . .
H5B H 0.5527 0.0557 0.4160 0.046 Uiso 1 1 calc R U . . .
C5A C 0.4841(6) 0.1173(3) 0.0648(6) 0.0335(11) Uani 1 1 d . . . . .
C6A C 0.3467(7) 0.0808(3) -0.1459(6) 0.0353(11) Uani 1 1 d . . . . .
C7 C 0.2675(7) 0.0321(4) -0.2585(6) 0.0407(13) Uani 1 1 d . . . . .
H7 H 0.2510 -0.0247 -0.2411 0.049 Uiso 1 1 calc R U . . .
C8 C 0.2131(8) 0.0692(4) -0.3972(7) 0.0465(14) Uani 1 1 d . . . . .
H8 H 0.1552 0.0375 -0.4742 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2415(8) 0.1515(4) -0.4258(7) 0.0497(15) Uani 1 1 d . . . . .
H9 H 0.2049 0.1752 -0.5225 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3244(7) 0.2005(4) -0.3120(6) 0.0440(13) Uani 1 1 d . . . . .
H10 H 0.3452 0.2568 -0.3313 0.053 Uiso 1 1 calc R U . . .
C10A C 0.3747(7) 0.1642(3) -0.1711(6) 0.0345(11) Uani 1 1 d . . . . .
C10B C 0.4814(6) 0.1954(3) -0.0336(6) 0.0328(11) Uani 1 1 d . . . . .
C11 C 0.4131(6) 0.2656(3) 0.0686(6) 0.0307(11) Uani 1 1 d . . . . .
C12 C 0.7410(7) 0.0048(3) 0.2923(6) 0.0355(11) Uani 1 1 d . . . . .
C13 C 0.7771(7) -0.0638(4) 0.3814(7) 0.0450(14) Uani 1 1 d . . . . .
H13 H 0.6987 -0.0836 0.4530 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9274(8) -0.1046(4) 0.3679(8) 0.0502(15) Uani 1 1 d . . . . .
H14 H 0.9509 -0.1516 0.4302 0.060 Uiso 1 1 calc R U . . .
C15 C 1.0413(8) -0.0765(4) 0.2640(7) 0.0483(15) Uani 1 1 d . . . . .
H15 H 1.1421 -0.1051 0.2522 0.058 Uiso 1 1 calc R U . . .
C16 C 1.0093(9) -0.0070(4) 0.1773(8) 0.0565(17) Uani 1 1 d . . . . .
H16 H 1.0894 0.0140 0.1087 0.068 Uiso 1 1 calc R U . . .
C17 C 0.8572(8) 0.0327(4) 0.1913(8) 0.0525(16) Uani 1 1 d . . . . .
H17 H 0.8341 0.0800 0.1295 0.063 Uiso 1 1 calc R U . . .
C18 C 0.6571(7) 0.2121(3) -0.0924(6) 0.0385(12) Uani 1 1 d . . . . .
H18A H 0.6531 0.2602 -0.1631 0.046 Uiso 1 1 calc R U . . .
H18B H 0.7298 0.2261 -0.0011 0.046 Uiso 1 1 calc R U . . .
C19 C 0.7318(8) 0.1414(4) -0.1785(7) 0.0471(14) Uani 1 1 d . . . . .
H19 H 0.6580 0.1083 -0.2393 0.057 Uiso 1 1 calc R U . . .
C20 C 0.8836(9) 0.1212(6) -0.1785(9) 0.071(2) Uani 1 1 d . . . . .
H20A H 0.9626 0.1522 -0.1197 0.085 Uiso 1 1 calc R U . . .
H20B H 0.9175 0.0751 -0.2375 0.085 Uiso 1 1 calc R U . . .
C21 C 0.2309(7) 0.2454(4) 0.1073(7) 0.0413(13) Uani 1 1 d . . . . .
H21A H 0.1644 0.2458 0.0081 0.050 Uiso 1 1 calc R U . . .
H21B H 0.2269 0.1891 0.1502 0.050 Uiso 1 1 calc R U . . .
C22 C 0.1519(8) 0.3019(4) 0.2213(7) 0.0455(14) Uani 1 1 d . . . . .
H22 H 0.2024 0.3072 0.3228 0.055 Uiso 1 1 calc R U . . .
C23 C 0.0183(9) 0.3448(5) 0.1913(9) 0.067(2) Uani 1 1 d . . . . .
H23A H -0.0357 0.3412 0.0911 0.080 Uiso 1 1 calc R U . . .
H23B H -0.0247 0.3795 0.2698 0.080 Uiso 1 1 calc R U . . .
C24 C 0.4097(7) 0.3486(3) -0.0182(7) 0.0403(13) Uani 1 1 d . . . . .
H24A H 0.3475 0.3420 -0.1191 0.048 Uiso 1 1 calc R U . . .
H24B H 0.3499 0.3888 0.0458 0.048 Uiso 1 1 calc R U . . .
H24O H 0.560(8) 0.4394(9) -0.032(8) 0.06(2) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b6 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b6'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b6'
_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
O24 C24 1.424(7) . ?
O24 H24O 0.980(7) . ?
N5 C5A 1.364(6) . ?
N5 C4A 1.428(7) . ?
N5 C5 1.470(6) . ?
N6 C5A 1.306(7) . ?
N6 C6A 1.431(7) . ?
C1 C1A 1.392(7) . ?
C1 C2 1.397(7) . ?
C1 H1 0.9500 . ?
C1A C4A 1.402(7) . ?
C1A C11 1.526(7) . ?
C2 C3 1.379(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(8) . ?
C3 H3 0.9500 . ?
C4 C4A 1.394(7) . ?
C4 H4 0.9500 . ?
C5 C12 1.511(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5A C10B 1.526(7) . ?
C6A C7 1.389(8) . ?
C6A C10A 1.400(8) . ?
C7 C8 1.389(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(8) . ?
C9 H9 0.9500 . ?
C10 C10A 1.389(7) . ?
C10 H10 0.9500 . ?
C10A C10B 1.525(7) . ?
C10B C18 1.549(7) . ?
C10B C11 1.551(7) . ?
C11 C24 1.544(7) . ?
C11 C21 1.561(7) . ?
C12 C17 1.372(8) . ?
C12 C13 1.381(8) . ?
C13 C14 1.397(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.504(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.276(9) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9500 . ?
C20 H20B 0.9500 . ?
C21 C22 1.497(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.310(9) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9500 . ?
C23 H23B 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
C24 O24 H24O 105(4) . . ?
C5A N5 C4A 118.9(4) . . ?
C5A N5 C5 120.4(4) . . ?
C4A N5 C5 120.4(4) . . ?
C5A N6 C6A 104.8(4) . . ?
C1A C1 C2 121.8(5) . . ?
C1A C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C1A C4A 117.0(5) . . ?
C1 C1A C11 122.0(5) . . ?
C4A C1A C11 120.9(5) . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C4A 120.1(5) . . ?
C3 C4 H4 119.9 . . ?
C4A C4 H4 119.9 . . ?
C4 C4A C1A 121.3(5) . . ?
C4 C4A N5 118.6(5) . . ?
C1A C4A N5 120.1(4) . . ?
N5 C5 C12 113.7(4) . . ?
N5 C5 H5A 108.8 . . ?
C12 C5 H5A 108.8 . . ?
N5 C5 H5B 108.8 . . ?
C12 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N6 C5A N5 124.3(5) . . ?
N6 C5A C10B 116.6(4) . . ?
N5 C5A C10B 119.1(5) . . ?
C7 C6A C10A 121.7(5) . . ?
C7 C6A N6 125.5(5) . . ?
C10A C6A N6 112.7(5) . . ?
C8 C7 C6A 117.8(6) . . ?
C8 C7 H7 121.1 . . ?
C6A C7 H7 121.1 . . ?
C9 C8 C7 121.5(6) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.5(6) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C10A C10 C9 118.3(6) . . ?
C10A C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C10A C6A 120.2(5) . . ?
C10 C10A C10B 131.9(5) . . ?
C6A C10A C10B 107.4(5) . . ?
C10A C10B C5A 98.1(4) . . ?
C10A C10B C18 108.6(4) . . ?
C5A C10B C18 109.0(4) . . ?
C10A C10B C11 118.3(4) . . ?
C5A C10B C11 108.1(4) . . ?
C18 C10B C11 113.5(4) . . ?
C1A C11 C24 112.2(4) . . ?
C1A C11 C10B 106.9(4) . . ?
C24 C11 C10B 112.5(4) . . ?
C1A C11 C21 110.2(4) . . ?
C24 C11 C21 106.4(4) . . ?
C10B C11 C21 108.5(4) . . ?
C17 C12 C13 118.4(5) . . ?
C17 C12 C5 122.8(5) . . ?
C13 C12 C5 118.8(5) . . ?
C12 C13 C14 120.9(5) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.0(6) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.3(6) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C12 C17 C16 121.5(6) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C10B 114.2(5) . . ?
C19 C18 H18A 108.7 . . ?
C10B C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C10B C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 127.0(7) . . ?
C20 C19 H19 116.5 . . ?
C18 C19 H19 116.5 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C22 C21 C11 115.6(5) . . ?
C22 C21 H21A 108.4 . . ?
C11 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C11 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C23 C22 C21 124.8(6) . . ?
C23 C22 H22 117.6 . . ?
C21 C22 H22 117.6 . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
O24 C24 C11 113.8(4) . . ?
O24 C24 H24A 108.8 . . ?
C11 C24 H24A 108.8 . . ?
O24 C24 H24B 108.8 . . ?
C11 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C1A C4A 2.4(8) . . . . ?
C2 C1 C1A C11 179.4(5) . . . . ?
C1A C1 C2 C3 0.9(8) . . . . ?
C1 C2 C3 C4 -1.8(8) . . . . ?
C2 C3 C4 C4A -0.5(8) . . . . ?
C3 C4 C4A C1A 3.9(8) . . . . ?
C3 C4 C4A N5 -174.3(5) . . . . ?
C1 C1A C4A C4 -4.8(7) . . . . ?
C11 C1A C4A C4 178.1(4) . . . . ?
C1 C1A C4A N5 173.5(5) . . . . ?
C11 C1A C4A N5 -3.6(7) . . . . ?
C5A N5 C4A C4 -166.5(5) . . . . ?
C5 N5 C4A C4 20.3(7) . . . . ?
C5A N5 C4A C1A 15.2(7) . . . . ?
C5 N5 C4A C1A -158.0(5) . . . . ?
C5A N5 C5 C12 95.2(6) . . . . ?
C4A N5 C5 C12 -91.6(6) . . . . ?
C6A N6 C5A N5 174.2(5) . . . . ?
C6A N6 C5A C10B -4.6(6) . . . . ?
C4A N5 C5A N6 -165.8(5) . . . . ?
C5 N5 C5A N6 7.5(8) . . . . ?
C4A N5 C5A C10B 13.0(7) . . . . ?
C5 N5 C5A C10B -173.8(5) . . . . ?
C5A N6 C6A C7 177.0(5) . . . . ?
C5A N6 C6A C10A 0.6(6) . . . . ?
C10A C6A C7 C8 -1.3(8) . . . . ?
N6 C6A C7 C8 -177.4(5) . . . . ?
C6A C7 C8 C9 2.2(9) . . . . ?
C7 C8 C9 C10 -1.3(10) . . . . ?
C8 C9 C10 C10A -0.7(9) . . . . ?
C9 C10 C10A C6A 1.6(8) . . . . ?
C9 C10 C10A C10B 172.1(5) . . . . ?
C7 C6A C10A C10 -0.6(8) . . . . ?
N6 C6A C10A C10 176.0(5) . . . . ?
C7 C6A C10A C10B -173.2(5) . . . . ?
N6 C6A C10A C10B 3.4(6) . . . . ?
C10 C10A C10B C5A -176.6(6) . . . . ?
C6A C10A C10B C5A -5.2(5) . . . . ?
C10 C10A C10B C18 -63.4(7) . . . . ?
C6A C10A C10B C18 108.0(5) . . . . ?
C10 C10A C10B C11 67.8(8) . . . . ?
C6A C10A C10B C11 -120.8(5) . . . . ?
N6 C5A C10B C10A 6.3(6) . . . . ?
N5 C5A C10B C10A -172.6(4) . . . . ?
N6 C5A C10B C18 -106.7(5) . . . . ?
N5 C5A C10B C18 74.5(6) . . . . ?
N6 C5A C10B C11 129.6(5) . . . . ?
N5 C5A C10B C11 -49.3(6) . . . . ?
C1 C1A C11 C24 27.0(7) . . . . ?
C4A C1A C11 C24 -156.1(5) . . . . ?
C1 C1A C11 C10B 150.8(5) . . . . ?
C4A C1A C11 C10B -32.3(6) . . . . ?
C1 C1A C11 C21 -91.4(6) . . . . ?
C4A C1A C11 C21 85.5(6) . . . . ?
C10A C10B C11 C1A 164.9(4) . . . . ?
C5A C10B C11 C1A 54.7(5) . . . . ?
C18 C10B C11 C1A -66.2(5) . . . . ?
C10A C10B C11 C24 -71.5(6) . . . . ?
C5A C10B C11 C24 178.4(4) . . . . ?
C18 C10B C11 C24 57.4(5) . . . . ?
C10A C10B C11 C21 45.9(6) . . . . ?
C5A C10B C11 C21 -64.2(5) . . . . ?
C18 C10B C11 C21 174.9(4) . . . . ?
N5 C5 C12 C17 -7.0(8) . . . . ?
N5 C5 C12 C13 175.9(5) . . . . ?
C17 C12 C13 C14 -0.8(9) . . . . ?
C5 C12 C13 C14 176.4(6) . . . . ?
C12 C13 C14 C15 -0.3(10) . . . . ?
C13 C14 C15 C16 2.0(10) . . . . ?
C14 C15 C16 C17 -2.6(11) . . . . ?
C13 C12 C17 C16 0.2(10) . . . . ?
C5 C12 C17 C16 -176.9(6) . . . . ?
C15 C16 C17 C12 1.5(11) . . . . ?
C10A C10B C18 C19 -51.9(6) . . . . ?
C5A C10B C18 C19 54.0(6) . . . . ?
C11 C10B C18 C19 174.4(5) . . . . ?
C10B C18 C19 C20 -146.3(7) . . . . ?
C1A C11 C21 C22 56.2(6) . . . . ?
C24 C11 C21 C22 -65.7(6) . . . . ?
C10B C11 C21 C22 173.0(5) . . . . ?
C11 C21 C22 C23 121.2(7) . . . . ?
C1A C11 C24 O24 53.6(6) . . . . ?
C10B C11 C24 O24 -67.0(6) . . . . ?
C21 C11 C24 O24 174.2(4) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O24 H24O N6 . . 2_655 2.847(6) 0.980(19) 1.877(19) 170(6) no

#==============================================================================
# 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_S16
_database_code_depnum_ccdc_archive 'CCDC 1478153'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_audit_creation_date             2016-04-25
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C41 H38 N4 O2'
_chemical_formula_moiety         'C41 H38 N4 O2'
_chemical_formula_weight         618.78
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      trigonal
_space_group_name_H-M_alt        'R -3:H'
_space_group_name_Hall           '-R 3'
_space_group_IT_number           148
loop_
_space_group_symop_operation_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                   24.722(4)
_cell_length_b                   24.722(4)
_cell_length_c                   13.524(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_volume                     7158.1(19)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    8344
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.02
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2952.00
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_T_max  0.998

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.315
_diffrn_reflns_number            14358
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_theta_max         27.299
_diffrn_reflns_theta_min         2.854
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3186
_reflns_number_gt                2731
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0735
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1746
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3186
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0946P)²+31.2290P] 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         1.37
_refine_diff_density_min         -0.65
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 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 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
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
O11 O 0.12888(8) 0.91124(8) 0.56729(12) 0.0260(4) Uani 1 1 d . . . . .
N5 N 0.16724(9) 0.94784(9) 0.87443(13) 0.0169(4) Uani 1 1 d . . . . .
N6 N 0.10357(9) 0.83853(9) 0.89084(14) 0.0185(4) Uani 1 1 d . . . . .
C1A C 0.18479(10) 0.98685(10) 0.70453(17) 0.0173(5) Uani 1 1 d . . . . .
C1 C 0.21049(11) 1.03649(11) 0.63874(17) 0.0203(5) Uani 1 1 d . . . . .
H1 H 0.2023 1.0288 0.5700 0.024 Uiso 1 1 calc R U . . .
C2 C 0.24816(11) 1.09750(11) 0.67220(18) 0.0213(5) Uani 1 1 d . . . . .
H2 H 0.2652 1.1314 0.6268 0.026 Uiso 1 1 calc R U . . .
C3 C 0.26052(10) 1.10816(11) 0.77229(18) 0.0204(5) Uani 1 1 d . . . . .
H3 H 0.2871 1.1495 0.7953 0.025 Uiso 1 1 calc R U . . .
C4 C 0.23447(10) 1.05906(10) 0.83973(17) 0.0190(5) Uani 1 1 d . . . . .
H4 H 0.2433 1.0670 0.9083 0.023 Uiso 1 1 calc R U . . .
C4A C 0.19541(10) 0.99811(10) 0.80665(16) 0.0164(5) Uani 1 1 d . . . . .
C5 C 0.19299(11) 0.95435(11) 0.97397(17) 0.0204(5) Uani 1 1 d . . . . .
H5A H 0.2247 0.9981 0.9856 0.024 Uiso 1 1 calc R U . . .
H5B H 0.1594 0.9413 1.0228 0.024 Uiso 1 1 calc R U . . .
H5C H 0.2121 0.9281 0.9802 0.024 Uiso 1 1 calc R U . . .
C5A C 0.12218(10) 0.89041(10) 0.84297(16) 0.0160(5) Uani 1 1 d . . . . .
C6A C 0.06076(10) 0.79112(10) 0.82640(17) 0.0179(5) Uani 1 1 d . . . . .
C7 C 0.02727(11) 0.72744(11) 0.84693(18) 0.0213(5) Uani 1 1 d . . . . .
H7 H 0.0327 0.7113 0.9076 0.026 Uiso 1 1 calc R U . . .
C8 C -0.01454(11) 0.68808(11) 0.77539(19) 0.0239(5) Uani 1 1 d . . . . .
H8 H -0.0383 0.6445 0.7881 0.029 Uiso 1 1 calc R U . . .
C9 C -0.02229(11) 0.71106(11) 0.68611(19) 0.0238(5) Uani 1 1 d . . . . .
H9 H -0.0512 0.6831 0.6388 0.029 Uiso 1 1 calc R U . . .
C10 C 0.01213(11) 0.77513(11) 0.66508(17) 0.0215(5) Uani 1 1 d . . . . .
H10 H 0.0071 0.7912 0.6041 0.026 Uiso 1 1 calc R U . . .
C10A C 0.05371(10) 0.81433(10) 0.73596(17) 0.0193(5) Uani 1 1 d . . . . .
C10B C 0.09128(10) 0.88452(10) 0.74294(16) 0.0172(5) Uani 1 1 d . . . . .
C11 C 0.14407(10) 0.92072(10) 0.67041(16) 0.0186(5) Uani 1 1 d . . . . .
C12 C 0.04771(11) 0.91348(11) 0.74464(19) 0.0229(5) Uani 1 1 d . . . . .
H12A H 0.0725 0.9577 0.7655 0.028 Uiso 1 1 calc R U . . .
H12B H 0.0325 0.9129 0.6767 0.028 Uiso 1 1 calc R U . . .
C13 C -0.00679(12) 0.88081(12) 0.8112(2) 0.0305(6) Uani 1 1 d . . . . .
H13 H -0.0368 0.8388 0.7954 0.037 Uiso 1 1 calc R U . . .
C14 C -0.01691(14) 0.90494(14) 0.8894(2) 0.0372(7) Uani 1 1 d . . . . .
H14A H 0.0120 0.9468 0.9077 0.045 Uiso 1 1 calc R U . . .
H14B H -0.0532 0.8807 0.9283 0.045 Uiso 1 1 calc R U . . .
C15 C 0.16899(12) 0.88967(11) 0.60831(18) 0.0251(5) Uani 1 1 d . . . . .
H15A H 0.2139 0.9132 0.5913 0.030 Uiso 1 1 calc R U . . .
H15B H 0.1513 0.8441 0.6167 0.030 Uiso 1 1 calc R U . . .
C21 C 0.0221(5) 0.9546(4) 0.4750(6) 0.071(3) Uani 0.5 1 d . . P . .
H21A H 0.0366 0.9247 0.4903 0.085 Uiso 0.5 1 calc R U P . .
H21B H 0.0203 0.9583 0.4024 0.085 Uiso 0.5 1 calc R U P . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku, ????)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    SIR97
_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
O11 C11 1.433(3) . ?
O11 C15 1.451(3) . ?
N5 C5A 1.362(3) . ?
N5 C4A 1.416(3) . ?
N5 C5 1.463(3) . ?
N6 C5A 1.298(3) . ?
N6 C6A 1.419(3) . ?
C1A C1 1.386(3) . ?
C1A C4A 1.407(3) . ?
C1A C11 1.501(3) . ?
C1 C2 1.394(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.396(3) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5A C10B 1.524(3) . ?
C6A C7 1.392(3) . ?
C6A C10A 1.398(3) . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.402(3) . ?
C9 H9 0.9500 . ?
C10 C10A 1.385(3) . ?
C10 H10 0.9500 . ?
C10A C10B 1.507(3) . ?
C10B C11 1.516(3) . ?
C10B C12 1.563(3) . ?
C11 C15 1.465(3) . ?
C12 C13 1.479(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.299(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C21 C21 1.621(10) 12_666 ?
C21 C21 1.621(10) 11_456 ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
C11 O11 C15 61.07(15) . . ?
C5A N5 C4A 119.97(19) . . ?
C5A N5 C5 119.08(18) . . ?
C4A N5 C5 120.21(18) . . ?
C5A N6 C6A 105.04(19) . . ?
C1 C1A C4A 119.8(2) . . ?
C1 C1A C11 121.9(2) . . ?
C4A C1A C11 118.3(2) . . ?
C1A C1 C2 120.8(2) . . ?
C1A C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C4A 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C4A C4 H4 120.0 . . ?
C4 C4A C1A 119.2(2) . . ?
C4 C4A N5 120.7(2) . . ?
C1A C4A N5 120.04(19) . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C5A N5 125.1(2) . . ?
N6 C5A C10B 115.79(19) . . ?
N5 C5A C10B 119.10(19) . . ?
C7 C6A C10A 120.9(2) . . ?
C7 C6A N6 126.0(2) . . ?
C10A C6A N6 113.12(19) . . ?
C6A C7 C8 117.7(2) . . ?
C6A C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C10A C10 C9 118.0(2) . . ?
C10A C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C10 C10A C6A 121.3(2) . . ?
C10 C10A C10B 131.6(2) . . ?
C6A C10A C10B 106.64(19) . . ?
C10A C10B C11 119.48(19) . . ?
C10A C10B C5A 99.00(17) . . ?
C11 C10B C5A 105.99(18) . . ?
C10A C10B C12 111.05(18) . . ?
C11 C10B C12 109.03(18) . . ?
C5A C10B C12 111.73(18) . . ?
O11 C11 C15 60.06(15) . . ?
O11 C11 C1A 117.09(19) . . ?
C15 C11 C1A 121.2(2) . . ?
O11 C11 C10B 117.08(18) . . ?
C15 C11 C10B 121.7(2) . . ?
C1A C11 C10B 110.77(18) . . ?
C13 C12 C10B 114.0(2) . . ?
C13 C12 H12A 108.8 . . ?
C10B C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C10B C12 H12B 108.8 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 125.2(3) . . ?
C14 C13 H13 117.4 . . ?
C12 C13 H13 117.4 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
O11 C15 C11 58.87(15) . . ?
O11 C15 H15A 117.9 . . ?
C11 C15 H15A 117.9 . . ?
O11 C15 H15B 117.9 . . ?
C11 C15 H15B 117.9 . . ?
H15A C15 H15B 115.0 . . ?
C21 C21 C21 103.9(6) 12_666 11_456 ?
C21 C21 H21A 111.0 12_666 . ?
C21 C21 H21A 111.0 11_456 . ?
C21 C21 H21B 111.0 12_666 . ?
C21 C21 H21B 111.0 11_456 . ?
H21A C21 H21B 109.0 . . ?

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
C4A C1A C1 C2 1.7(3) . . . . ?
C11 C1A C1 C2 180.0(2) . . . . ?
C1A C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C2 C3 C4 C4A 0.1(3) . . . . ?
C3 C4 C4A C1A 2.4(3) . . . . ?
C3 C4 C4A N5 -178.4(2) . . . . ?
C1 C1A C4A C4 -3.3(3) . . . . ?
C11 C1A C4A C4 178.3(2) . . . . ?
C1 C1A C4A N5 177.5(2) . . . . ?
C11 C1A C4A N5 -0.9(3) . . . . ?
C5A N5 C4A C4 170.2(2) . . . . ?
C5 N5 C4A C4 -19.8(3) . . . . ?
C5A N5 C4A C1A -10.6(3) . . . . ?
C5 N5 C4A C1A 159.5(2) . . . . ?
C6A N6 C5A N5 -175.0(2) . . . . ?
C6A N6 C5A C10B 3.4(2) . . . . ?
C4A N5 C5A N6 163.2(2) . . . . ?
C5 N5 C5A N6 -7.0(3) . . . . ?
C4A N5 C5A C10B -15.2(3) . . . . ?
C5 N5 C5A C10B 174.67(19) . . . . ?
C5A N6 C6A C7 -178.2(2) . . . . ?
C5A N6 C6A C10A 1.1(3) . . . . ?
C10A C6A C7 C8 -1.6(3) . . . . ?
N6 C6A C7 C8 177.7(2) . . . . ?
C6A C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C10A -0.1(3) . . . . ?
C9 C10 C10A C6A -0.8(3) . . . . ?
C9 C10 C10A C10B -171.4(2) . . . . ?
C7 C6A C10A C10 1.7(3) . . . . ?
N6 C6A C10A C10 -177.6(2) . . . . ?
C7 C6A C10A C10B 174.4(2) . . . . ?
N6 C6A C10A C10B -5.0(3) . . . . ?
C10 C10A C10B C11 -68.1(3) . . . . ?
C6A C10A C10B C11 120.2(2) . . . . ?
C10 C10A C10B C5A 177.7(2) . . . . ?
C6A C10A C10B C5A 6.1(2) . . . . ?
C10 C10A C10B C12 60.1(3) . . . . ?
C6A C10A C10B C12 -111.5(2) . . . . ?
N6 C5A C10B C10A -6.1(2) . . . . ?
N5 C5A C10B C10A 172.42(19) . . . . ?
N6 C5A C10B C11 -130.4(2) . . . . ?
N5 C5A C10B C11 48.1(3) . . . . ?
N6 C5A C10B C12 110.9(2) . . . . ?
N5 C5A C10B C12 -70.5(2) . . . . ?
C15 O11 C11 C1A 112.1(2) . . . . ?
C15 O11 C11 C10B -112.7(2) . . . . ?
C1 C1A C11 O11 -4.5(3) . . . . ?
C4A C1A C11 O11 173.82(19) . . . . ?
C1 C1A C11 C15 65.2(3) . . . . ?
C4A C1A C11 C15 -116.4(2) . . . . ?
C1 C1A C11 C10B -142.4(2) . . . . ?
C4A C1A C11 C10B 36.0(3) . . . . ?
C10A C10B C11 O11 56.0(3) . . . . ?
C5A C10B C11 O11 166.41(18) . . . . ?
C12 C10B C11 O11 -73.2(2) . . . . ?
C10A C10B C11 C15 -13.9(3) . . . . ?
C5A C10B C11 C15 96.5(2) . . . . ?
C12 C10B C11 C15 -143.1(2) . . . . ?
C10A C10B C11 C1A -166.19(19) . . . . ?
C5A C10B C11 C1A -55.8(2) . . . . ?
C12 C10B C11 C1A 64.6(2) . . . . ?
C10A C10B C12 C13 44.7(3) . . . . ?
C11 C10B C12 C13 178.4(2) . . . . ?
C5A C10B C12 C13 -64.8(3) . . . . ?
C10B C12 C13 C14 115.6(3) . . . . ?
C1A C11 C15 O11 -105.4(2) . . . . ?
C10B C11 C15 O11 105.2(2) . . . . ?

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

#==============================================================================
# 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 1478154'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_RFACR01_27                  
;
PROBLEM: The value of the weighted R factor is > 0.45
RESPONSE: Poor quality crystals.
;
_vrf_PLAT084_27                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.46 Report
RESPONSE:  Poor quality crystals.
;
# end Validation Reply Form
_audit_creation_date             2016-05-04
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C28 H27 B F4 N4'
_chemical_formula_moiety         'C28 H27 B F4 N4'
_chemical_formula_weight         506.35
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   6.691(5)
_cell_length_b                   29.96(2)
_cell_length_c                   12.952(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.20(2)
_cell_angle_gamma                90.0000
_cell_volume                     2517(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1514
_cell_measurement_theta_min      20.88
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056.00
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.334
_exptl_absorpt_correction_T_max  0.975

#==============================================================================
# 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            33985
_diffrn_reflns_av_R_equivalents  0.2363
_diffrn_reflns_theta_max         68.009
_diffrn_reflns_theta_min         2.950
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4504
_reflns_number_gt                2519
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.2607
_refine_ls_R_factor_gt           0.1742
_refine_ls_wR_factor_ref         0.4607
_refine_ls_wR_factor_gt          0.4114
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4504
_refine_ls_number_parameters     336
_refine_ls_goodness_of_fit_ref   1.382
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)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          0.001
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.55
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.026(4)

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)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 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)
;

#==============================================================================
# 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 0.6606(10) 0.2787(2) 0.1492(8) 0.211(4) Uani 1 1 d . . . . .
F2 F 0.9361(7) 0.23920(18) 0.2233(4) 0.1258(19) Uani 1 1 d . . . . .
F3 F 0.8736(15) 0.2695(3) 0.0606(6) 0.205(4) Uani 1 1 d . . . . .
F4 F 0.9596(15) 0.3111(3) 0.1976(7) 0.247(5) Uani 1 1 d . . . . .
N5 N 0.4042(10) 0.0392(2) 0.2902(5) 0.092(2) Uani 1 1 d . . . . .
N6 N 0.1226(11) 0.0453(3) 0.1401(6) 0.114(3) Uani 1 1 d . . . . .
N20 N 0.5360(8) 0.1943(2) 0.2254(5) 0.0922(19) Uani 1 1 d . . . . .
H20 H 0.5908 0.2211 0.2318 0.111 Uiso 1 1 calc R U . . .
N22 N 0.3519(8) 0.2096(2) 0.3550(5) 0.0865(18) Uani 1 1 d . . . . .
C1 C 0.6870(10) 0.1313(2) 0.4575(6) 0.079(2) Uani 1 1 d . . . . .
H1 H 0.6810 0.1627 0.4658 0.094 Uiso 1 1 calc R U . . .
C1A C 0.5370(10) 0.1106(3) 0.3779(5) 0.076(2) Uani 1 1 d . . . . .
C2 C 0.8435(11) 0.1078(3) 0.5246(6) 0.083(2) Uani 1 1 d . . . . .
H2 H 0.9424 0.1229 0.5784 0.099 Uiso 1 1 calc R U . . .
C3 C 0.8560(12) 0.0619(3) 0.5132(6) 0.094(2) Uani 1 1 d . . . . .
H3 H 0.9647 0.0456 0.5586 0.113 Uiso 1 1 calc R U . . .
C4 C 0.7112(14) 0.0400(3) 0.4363(6) 0.094(2) Uani 1 1 d . . . . .
H4 H 0.7191 0.0085 0.4303 0.112 Uiso 1 1 calc R U . . .
C4A C 0.5529(11) 0.0632(3) 0.3668(6) 0.086(2) Uani 1 1 d . . . . .
C5 C 0.3686(15) -0.0077(3) 0.2979(7) 0.114(3) Uani 1 1 d . . . . .
H5A H 0.2282 -0.0146 0.2548 0.137 Uiso 1 1 calc R U . . .
H5B H 0.3729 -0.0149 0.3729 0.137 Uiso 1 1 calc R U . . .
C5A C 0.2774(13) 0.0629(3) 0.2080(7) 0.095(3) Uani 1 1 d . . . . .
C6A C 0.0291(12) 0.0827(4) 0.0765(7) 0.111(3) Uani 1 1 d . . . . .
C7 C -0.1416(15) 0.0827(6) -0.0116(9) 0.162(6) Uani 1 1 d . . . . .
H7 H -0.2129 0.0557 -0.0348 0.195 Uiso 1 1 calc R U . . .
C8 C -0.2068(18) 0.1230(6) -0.0654(10) 0.163(7) Uani 1 1 d . . . . .
H8 H -0.3228 0.1229 -0.1249 0.196 Uiso 1 1 calc R U . . .
C9 C -0.1075(14) 0.1619(5) -0.0339(7) 0.144(5) Uani 1 1 d . . . . .
H9 H -0.1553 0.1886 -0.0714 0.172 Uiso 1 1 calc R U . . .
C10 C 0.0684(11) 0.1633(4) 0.0547(6) 0.113(3) Uani 1 1 d . . . . .
H10 H 0.1372 0.1907 0.0774 0.136 Uiso 1 1 calc R U . . .
C10A C 0.1340(11) 0.1243(4) 0.1056(6) 0.099(3) Uani 1 1 d . . . . .
C10B C 0.3249(10) 0.1122(3) 0.1936(5) 0.081(2) Uani 1 1 d . . . . .
C11 C 0.3606(9) 0.1363(2) 0.3008(5) 0.0695(18) Uani 1 1 d . . . . .
C12 C 0.5221(13) -0.0375(4) 0.2610(6) 0.102(3) Uani 1 1 d . . . . .
C13 C 0.5540(13) -0.0809(4) 0.3014(7) 0.103(3) Uani 1 1 d . . . . .
H13 H 0.4862 -0.0905 0.3539 0.123 Uiso 1 1 calc R U . . .
C14 C 0.6818(14) -0.1097(3) 0.2663(7) 0.101(3) Uani 1 1 d . . . . .
H14 H 0.6973 -0.1396 0.2912 0.121 Uiso 1 1 calc R U . . .
C15 C 0.7883(14) -0.0946(4) 0.1938(8) 0.116(3) Uani 1 1 d . . . . .
H15 H 0.8849 -0.1137 0.1731 0.140 Uiso 1 1 calc R U . . .
C16 C 0.7555(16) -0.0515(4) 0.1506(8) 0.118(3) Uani 1 1 d . . . . .
H16 H 0.8244 -0.0418 0.0985 0.142 Uiso 1 1 calc R U . . .
C17 C 0.6210(14) -0.0232(3) 0.1849(7) 0.117(3) Uani 1 1 d . . . . .
H17 H 0.5968 0.0061 0.1562 0.140 Uiso 1 1 calc R U . . .
C18 C 0.5196(10) 0.1175(3) 0.1525(6) 0.081(2) Uani 1 1 d . . . . .
H18A H 0.6360 0.1025 0.2024 0.098 Uiso 1 1 calc R U . . .
H18B H 0.4980 0.1025 0.0825 0.098 Uiso 1 1 calc R U . . .
C19 C 0.5747(10) 0.1654(3) 0.1410(6) 0.090(2) Uani 1 1 d . . . . .
H19A H 0.7225 0.1673 0.1413 0.108 Uiso 1 1 calc R U . . .
H19B H 0.4940 0.1766 0.0713 0.108 Uiso 1 1 calc R U . . .
C21 C 0.4219(11) 0.1825(3) 0.2941(6) 0.082(2) Uani 1 1 d . . . . .
C23 C 0.2259(11) 0.1850(3) 0.4156(5) 0.089(2) Uani 1 1 d . . . . .
H23A H 0.0982 0.2015 0.4166 0.107 Uiso 1 1 calc R U . . .
H23B H 0.3045 0.1793 0.4897 0.107 Uiso 1 1 calc R U . . .
C24 C 0.1775(11) 0.1411(3) 0.3517(5) 0.088(2) Uani 1 1 d . . . . .
H24A H 0.1701 0.1156 0.3991 0.105 Uiso 1 1 calc R U . . .
H24B H 0.0458 0.1434 0.2967 0.105 Uiso 1 1 calc R U . . .
C25 C 0.3890(14) 0.2575(3) 0.3679(6) 0.112(3) Uani 1 1 d . . . . .
H25A H 0.3620 0.2717 0.2976 0.135 Uiso 1 1 calc R U . . .
H25B H 0.5327 0.2627 0.4060 0.135 Uiso 1 1 calc R U . . .
H25C H 0.2971 0.2702 0.4086 0.135 Uiso 1 1 calc R U . . .
B1 B 0.8604(19) 0.2754(4) 0.1633(9) 0.107(4) Uani 1 1 d . . . . .


#==============================================================================
_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    SIR97
_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
F1 B1 1.307(12) . ?
F2 B1 1.356(11) . ?
F3 B1 1.366(13) . ?
F4 B1 1.281(12) . ?
N5 C5A 1.383(11) . ?
N5 C4A 1.416(9) . ?
N5 C5 1.432(10) . ?
N6 C5A 1.294(9) . ?
N6 C6A 1.438(12) . ?
N20 C21 1.354(9) . ?
N20 C19 1.465(9) . ?
N20 H20 0.8800 . ?
N22 C21 1.297(9) . ?
N22 C25 1.459(10) . ?
N22 C23 1.481(9) . ?
C1 C2 1.379(10) . ?
C1 C1A 1.396(9) . ?
C1 H1 0.9500 . ?
C1A C4A 1.433(11) . ?
C1A C11 1.551(9) . ?
C2 C3 1.386(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(11) . ?
C3 H3 0.9500 . ?
C4 C4A 1.395(11) . ?
C4 H4 0.9500 . ?
C5 C12 1.524(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5A C10B 1.533(11) . ?
C6A C7 1.403(14) . ?
C6A C10A 1.436(13) . ?
C7 C8 1.408(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.354(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.429(12) . ?
C9 H9 0.9500 . ?
C10 C10A 1.360(12) . ?
C10 H10 0.9500 . ?
C10A C10B 1.532(11) . ?
C10B C11 1.530(9) . ?
C10B C18 1.531(9) . ?
C11 C21 1.452(10) . ?
C11 C24 1.534(9) . ?
C12 C17 1.383(11) . ?
C12 C13 1.397(12) . ?
C13 C14 1.369(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(13) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.499(10) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C23 C24 1.544(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C5A N5 C4A 118.1(7) . . ?
C5A N5 C5 118.4(7) . . ?
C4A N5 C5 123.3(8) . . ?
C5A N6 C6A 103.7(8) . . ?
C21 N20 C19 124.6(7) . . ?
C21 N20 H20 117.7 . . ?
C19 N20 H20 117.7 . . ?
C21 N22 C25 127.5(7) . . ?
C21 N22 C23 110.4(7) . . ?
C25 N22 C23 122.1(7) . . ?
C2 C1 C1A 122.4(7) . . ?
C2 C1 H1 118.8 . . ?
C1A C1 H1 118.8 . . ?
C1 C1A C4A 117.2(7) . . ?
C1 C1A C11 123.4(7) . . ?
C4A C1A C11 119.4(6) . . ?
C1 C2 C3 119.7(7) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.0(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C4A 121.3(8) . . ?
C3 C4 H4 119.3 . . ?
C4A C4 H4 119.3 . . ?
C4 C4A N5 119.4(8) . . ?
C4 C4A C1A 119.4(7) . . ?
N5 C4A C1A 121.1(8) . . ?
N5 C5 C12 114.7(7) . . ?
N5 C5 H5A 108.6 . . ?
C12 C5 H5A 108.6 . . ?
N5 C5 H5B 108.6 . . ?
C12 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
N6 C5A N5 123.5(9) . . ?
N6 C5A C10B 117.7(9) . . ?
N5 C5A C10B 118.8(6) . . ?
C7 C6A C10A 117.4(12) . . ?
C7 C6A N6 128.3(11) . . ?
C10A C6A N6 114.2(8) . . ?
C6A C7 C8 119.7(14) . . ?
C6A C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 121.2(13) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.0(14) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C10A C10 C9 117.8(11) . . ?
C10A C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C10A C6A 122.7(9) . . ?
C10 C10A C10B 132.4(8) . . ?
C6A C10A C10B 104.7(9) . . ?
C11 C10B C18 108.1(5) . . ?
C11 C10B C10A 118.6(6) . . ?
C18 C10B C10A 110.0(6) . . ?
C11 C10B C5A 109.6(6) . . ?
C18 C10B C5A 111.2(6) . . ?
C10A C10B C5A 99.1(7) . . ?
C21 C11 C10B 112.2(6) . . ?
C21 C11 C24 101.7(6) . . ?
C10B C11 C24 118.1(5) . . ?
C21 C11 C1A 109.3(5) . . ?
C10B C11 C1A 106.0(5) . . ?
C24 C11 C1A 109.4(5) . . ?
C17 C12 C13 120.0(9) . . ?
C17 C12 C5 121.2(10) . . ?
C13 C12 C5 118.8(8) . . ?
C14 C13 C12 120.9(8) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.0(9) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C16 121.0(9) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.0(9) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C12 C17 C16 120.0(10) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C10B 112.6(6) . . ?
C19 C18 H18A 109.1 . . ?
C10B C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C10B C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
N20 C19 C18 113.5(6) . . ?
N20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
N20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
N22 C21 N20 125.6(8) . . ?
N22 C21 C11 114.3(7) . . ?
N20 C21 C11 120.1(7) . . ?
N22 C23 C24 102.2(6) . . ?
N22 C23 H23A 111.3 . . ?
C24 C23 H23A 111.3 . . ?
N22 C23 H23B 111.3 . . ?
C24 C23 H23B 111.3 . . ?
H23A C23 H23B 109.2 . . ?
C11 C24 C23 103.1(5) . . ?
C11 C24 H24A 111.1 . . ?
C23 C24 H24A 111.1 . . ?
C11 C24 H24B 111.1 . . ?
C23 C24 H24B 111.1 . . ?
H24A C24 H24B 109.1 . . ?
N22 C25 H25A 109.5 . . ?
N22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F4 B1 F1 114.2(13) . . ?
F4 B1 F2 112.3(9) . . ?
F1 B1 F2 111.5(8) . . ?
F4 B1 F3 107.0(9) . . ?
F1 B1 F3 100.5(10) . . ?
F2 B1 F3 110.5(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C1A C4A -0.9(9) . . . . ?
C2 C1 C1A C11 -179.4(6) . . . . ?
C1A C1 C2 C3 0.6(10) . . . . ?
C1 C2 C3 C4 -0.9(10) . . . . ?
C2 C3 C4 C4A 1.6(10) . . . . ?
C3 C4 C4A N5 -178.6(6) . . . . ?
C3 C4 C4A C1A -2.0(10) . . . . ?
C5A N5 C4A C4 -166.0(6) . . . . ?
C5 N5 C4A C4 18.7(10) . . . . ?
C5A N5 C4A C1A 17.5(9) . . . . ?
C5 N5 C4A C1A -157.9(7) . . . . ?
C1 C1A C4A C4 1.6(9) . . . . ?
C11 C1A C4A C4 -179.8(6) . . . . ?
C1 C1A C4A N5 178.1(6) . . . . ?
C11 C1A C4A N5 -3.3(9) . . . . ?
C5A N5 C5 C12 104.1(8) . . . . ?
C4A N5 C5 C12 -80.6(9) . . . . ?
C6A N6 C5A N5 175.5(6) . . . . ?
C6A N6 C5A C10B -6.3(8) . . . . ?
C4A N5 C5A N6 -172.5(6) . . . . ?
C5 N5 C5A N6 3.1(10) . . . . ?
C4A N5 C5A C10B 9.3(9) . . . . ?
C5 N5 C5A C10B -175.1(6) . . . . ?
C5A N6 C6A C7 177.8(7) . . . . ?
C5A N6 C6A C10A 1.3(8) . . . . ?
C10A C6A C7 C8 -1.9(12) . . . . ?
N6 C6A C7 C8 -178.3(9) . . . . ?
C6A C7 C8 C9 0.2(16) . . . . ?
C7 C8 C9 C10 0.4(15) . . . . ?
C8 C9 C10 C10A 0.8(12) . . . . ?
C9 C10 C10A C6A -2.6(11) . . . . ?
C9 C10 C10A C10B 172.5(7) . . . . ?
C7 C6A C10A C10 3.2(11) . . . . ?
N6 C6A C10A C10 -179.9(6) . . . . ?
C7 C6A C10A C10B -173.1(6) . . . . ?
N6 C6A C10A C10B 3.8(8) . . . . ?
C10 C10A C10B C11 59.5(11) . . . . ?
C6A C10A C10B C11 -124.7(7) . . . . ?
C10 C10A C10B C18 -65.6(10) . . . . ?
C6A C10A C10B C18 110.2(7) . . . . ?
C10 C10A C10B C5A 177.8(8) . . . . ?
C6A C10A C10B C5A -6.4(6) . . . . ?
N6 C5A C10B C11 133.3(6) . . . . ?
N5 C5A C10B C11 -48.4(8) . . . . ?
N6 C5A C10B C18 -107.3(7) . . . . ?
N5 C5A C10B C18 71.0(8) . . . . ?
N6 C5A C10B C10A 8.4(7) . . . . ?
N5 C5A C10B C10A -173.3(6) . . . . ?
C18 C10B C11 C21 54.3(7) . . . . ?
C10A C10B C11 C21 -71.7(8) . . . . ?
C5A C10B C11 C21 175.6(6) . . . . ?
C18 C10B C11 C24 172.1(6) . . . . ?
C10A C10B C11 C24 46.1(10) . . . . ?
C5A C10B C11 C24 -66.6(8) . . . . ?
C18 C10B C11 C1A -64.9(7) . . . . ?
C10A C10B C11 C1A 169.1(6) . . . . ?
C5A C10B C11 C1A 56.4(7) . . . . ?
C1 C1A C11 C21 23.2(8) . . . . ?
C4A C1A C11 C21 -155.2(6) . . . . ?
C1 C1A C11 C10B 144.4(6) . . . . ?
C4A C1A C11 C10B -34.1(7) . . . . ?
C1 C1A C11 C24 -87.3(7) . . . . ?
C4A C1A C11 C24 94.2(7) . . . . ?
N5 C5 C12 C17 -27.9(11) . . . . ?
N5 C5 C12 C13 155.4(8) . . . . ?
C17 C12 C13 C14 -0.3(12) . . . . ?
C5 C12 C13 C14 176.4(7) . . . . ?
C12 C13 C14 C15 3.3(12) . . . . ?
C13 C14 C15 C16 -4.6(12) . . . . ?
C14 C15 C16 C17 2.8(13) . . . . ?
C13 C12 C17 C16 -1.5(12) . . . . ?
C5 C12 C17 C16 -178.1(8) . . . . ?
C15 C16 C17 C12 0.3(13) . . . . ?
C11 C10B C18 C19 -57.8(8) . . . . ?
C10A C10B C18 C19 73.2(8) . . . . ?
C5A C10B C18 C19 -178.1(6) . . . . ?
C21 N20 C19 C18 -13.8(9) . . . . ?
C10B C18 C19 N20 37.4(8) . . . . ?
C25 N22 C21 N20 -3.8(11) . . . . ?
C23 N22 C21 N20 177.5(6) . . . . ?
C25 N22 C21 C11 178.7(6) . . . . ?
C23 N22 C21 C11 0.0(8) . . . . ?
C19 N20 C21 N22 -165.7(6) . . . . ?
C19 N20 C21 C11 11.7(9) . . . . ?
C10B C11 C21 N22 145.1(6) . . . . ?
C24 C11 C21 N22 17.9(7) . . . . ?
C1A C11 C21 N22 -97.7(7) . . . . ?
C10B C11 C21 N20 -32.6(8) . . . . ?
C24 C11 C21 N20 -159.7(6) . . . . ?
C1A C11 C21 N20 84.7(7) . . . . ?
C21 N22 C23 C24 -17.8(7) . . . . ?
C25 N22 C23 C24 163.4(6) . . . . ?
C21 C11 C24 C23 -27.0(7) . . . . ?
C10B C11 C24 C23 -150.3(6) . . . . ?
C1A C11 C24 C23 88.5(7) . . . . ?
N22 C23 C24 C11 27.2(7) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N20 H20 F1 . . . 2.909(11) 0.880 2.140 145.7 no
N20 H20 F2 . . . 3.003(8) 0.880 2.402 125.8 no

#==============================================================================
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1486344'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_audit_creation_date             2015-09-20
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C29 H31 N3 O S'
_chemical_formula_moiety         'C29 H31 N3 O S'
_chemical_formula_weight         469.64
_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                   13.438(3)
_cell_length_b                   14.165(2)
_cell_length_c                   13.5796(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.657(3)
_cell_angle_gamma                90.0000
_cell_volume                     2579.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3246
_cell_measurement_theta_min      24.20
_cell_measurement_theta_max      74.60
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000.00
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_T_max  0.937

#==============================================================================
# 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            28126
_diffrn_reflns_av_R_equivalents  0.1235
_diffrn_reflns_theta_max         68.342
_diffrn_reflns_theta_min         4.488
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_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             8712
_reflns_number_gt                8450
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1505
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         8712
_refine_ls_number_parameters     627
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0727P)²+0.2584P] 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         0.28
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 3168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(11)

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)
;
S S 0.3331 0.5567
;
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
S11 S 0.56625(6) 0.72246(7) 0.71872(6) 0.0297(2) Uani 1 1 d . . . . .
S41 S 0.69638(6) 0.95396(6) 0.43040(6) 0.0300(2) Uani 1 1 d . . . . .
O11 O 0.47963(19) 0.6720(2) 0.6682(2) 0.0352(6) Uani 1 1 d . . . . .
O41 O 0.64672(19) 0.9286(2) 0.5223(2) 0.0355(6) Uani 1 1 d . . . . .
N5 N 0.8314(2) 0.6043(2) 0.4428(2) 0.0319(7) Uani 1 1 d . . . . .
N6 N 0.9194(2) 0.5499(2) 0.5881(2) 0.0320(7) Uani 1 1 d . . . . .
N11 N 0.6482(2) 0.7548(2) 0.6383(2) 0.0293(7) Uani 1 1 d D . . . .
N35 N 0.4059(2) 0.8171(2) 0.1671(2) 0.0320(7) Uani 1 1 d . . . . .
N36 N 0.5437(2) 0.7858(2) 0.0737(2) 0.0336(7) Uani 1 1 d . . . . .
N41 N 0.6141(2) 0.9887(2) 0.3415(2) 0.0283(7) Uani 1 1 d D . . . .
C1 C 0.5688(3) 0.6891(3) 0.4457(3) 0.0319(8) Uani 1 1 d . . . . .
H1 H 0.5231 0.7113 0.4910 0.038 Uiso 1 1 calc R U . . .
C1A C 0.6667(3) 0.6695(3) 0.4797(3) 0.0303(8) Uani 1 1 d . . . . .
C2 C 0.5365(3) 0.6770(3) 0.3479(3) 0.0323(8) Uani 1 1 d . . . . .
H2 H 0.4688 0.6888 0.3269 0.039 Uiso 1 1 calc R U . . .
C3 C 0.6035(3) 0.6475(3) 0.2802(3) 0.0350(9) Uani 1 1 d . . . . .
H3 H 0.5822 0.6415 0.2124 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7012(3) 0.6269(3) 0.3113(3) 0.0334(8) Uani 1 1 d . . . . .
H4 H 0.7466 0.6067 0.2647 0.040 Uiso 1 1 calc R U . . .
C4A C 0.7337(3) 0.6356(3) 0.4113(3) 0.0288(8) Uani 1 1 d . . . . .
C5 C 0.8851(3) 0.5396(3) 0.3813(3) 0.0348(9) Uani 1 1 d . . . . .
H5A H 0.8369 0.4940 0.3502 0.042 Uiso 1 1 calc R U . . .
H5B H 0.9336 0.5033 0.4242 0.042 Uiso 1 1 calc R U . . .
C5A C 0.8579(3) 0.6069(3) 0.5417(3) 0.0292(8) Uani 1 1 d . . . . .
C6A C 0.9148(3) 0.5732(3) 0.6906(3) 0.0324(8) Uani 1 1 d . . . . .
C7 C 0.9607(3) 0.5250(3) 0.7689(3) 0.0399(10) Uani 1 1 d . . . . .
H7 H 1.0039 0.4734 0.7586 0.048 Uiso 1 1 calc R U . . .
C8 C 0.9418(3) 0.5546(4) 0.8640(3) 0.0433(10) Uani 1 1 d . . . . .
H8 H 0.9716 0.5215 0.9191 0.052 Uiso 1 1 calc R U . . .
C9 C 0.8805(3) 0.6312(4) 0.8797(3) 0.0427(10) Uani 1 1 d . . . . .
H9 H 0.8694 0.6504 0.9452 0.051 Uiso 1 1 calc R U . . .
C10 C 0.8346(3) 0.6804(3) 0.7995(3) 0.0357(9) Uani 1 1 d . . . . .
H10 H 0.7931 0.7334 0.8094 0.043 Uiso 1 1 calc R U . . .
C10A C 0.8516(3) 0.6496(3) 0.7056(3) 0.0302(8) Uani 1 1 d . . . . .
C10B C 0.8118(3) 0.6827(3) 0.6050(3) 0.0293(8) Uani 1 1 d . . . . .
C11 C 0.6972(3) 0.6766(3) 0.5895(3) 0.0292(8) Uani 1 1 d . . . . .
H11 H 0.6760 0.6167 0.6211 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5158(3) 0.8392(3) 0.7488(3) 0.0344(9) Uani 1 1 d . . . . .
C13 C 0.6007(3) 0.9054(3) 0.7836(3) 0.0425(10) Uani 1 1 d . . . . .
H13A H 0.5729 0.9644 0.8076 0.051 Uiso 1 1 calc R U . . .
H13B H 0.6421 0.9190 0.7285 0.051 Uiso 1 1 calc R U . . .
H13C H 0.6415 0.8752 0.8371 0.051 Uiso 1 1 calc R U . . .
C14 C 0.4477(3) 0.8174(4) 0.8327(3) 0.0421(10) Uani 1 1 d . . . . .
H14A H 0.3927 0.7768 0.8077 0.051 Uiso 1 1 calc R U . . .
H14B H 0.4209 0.8764 0.8576 0.051 Uiso 1 1 calc R U . . .
H14C H 0.4863 0.7849 0.8862 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4553(3) 0.8778(3) 0.6597(3) 0.0384(9) Uani 1 1 d . . . . .
H15A H 0.5000 0.8940 0.6080 0.046 Uiso 1 1 calc R U . . .
H15B H 0.4193 0.9345 0.6788 0.046 Uiso 1 1 calc R U . . .
H15C H 0.4074 0.8300 0.6348 0.046 Uiso 1 1 calc R U . . .
C16 C 0.9406(3) 0.5868(4) 0.3007(3) 0.0387(10) Uani 1 1 d . . . . .
C17 C 0.9414(4) 0.6823(4) 0.2851(4) 0.0496(11) Uani 1 1 d . . . . .
H17 H 0.9059 0.7225 0.3266 0.059 Uiso 1 1 calc R U . . .
C18 C 0.9933(4) 0.7217(5) 0.2094(4) 0.0645(14) Uani 1 1 d . . . . .
H18 H 0.9921 0.7881 0.1994 0.077 Uiso 1 1 calc R U . . .
C19 C 1.0465(4) 0.6649(5) 0.1487(4) 0.0635(15) Uani 1 1 d . . . . .
H19 H 1.0828 0.6915 0.0977 0.076 Uiso 1 1 calc R U . . .
C20 C 1.0455(4) 0.5687(5) 0.1640(4) 0.0648(17) Uani 1 1 d . . . . .
H20 H 1.0807 0.5287 0.1222 0.078 Uiso 1 1 calc R U . . .
C21 C 0.9940(4) 0.5293(4) 0.2394(3) 0.0501(12) Uani 1 1 d . . . . .
H21 H 0.9951 0.4629 0.2492 0.060 Uiso 1 1 calc R U . . .
C22 C 0.8520(3) 0.7811(3) 0.5784(3) 0.0329(8) Uani 1 1 d . . . . .
H22A H 0.8288 0.7965 0.5096 0.039 Uiso 1 1 calc R U . . .
H22B H 0.8240 0.8289 0.6221 0.039 Uiso 1 1 calc R U . . .
C23 C 0.9642(3) 0.7869(3) 0.5883(3) 0.0387(9) Uani 1 1 d . . . . .
H23 H 0.9963 0.7691 0.6499 0.046 Uiso 1 1 calc R U . . .
C24 C 1.0216(3) 0.8147(3) 0.5187(4) 0.0468(11) Uani 1 1 d . . . . .
H24A H 0.9926 0.8332 0.4560 0.056 Uiso 1 1 calc R U . . .
H24B H 1.0919 0.8163 0.5311 0.056 Uiso 1 1 calc R U . . .
C31 C 0.4185(3) 0.9406(3) 0.4088(3) 0.0305(8) Uani 1 1 d . . . . .
H31 H 0.4653 0.9726 0.4523 0.037 Uiso 1 1 calc R U . . .
C31A C 0.4488(3) 0.9053(3) 0.3200(3) 0.0297(8) Uani 1 1 d . . . . .
C32 C 0.3199(3) 0.9298(3) 0.4353(3) 0.0344(8) Uani 1 1 d . . . . .
H32 H 0.3008 0.9526 0.4971 0.041 Uiso 1 1 calc R U . . .
C33 C 0.2511(3) 0.8861(3) 0.3715(3) 0.0362(9) Uani 1 1 d . . . . .
H33 H 0.1840 0.8804 0.3887 0.043 Uiso 1 1 calc R U . . .
C34 C 0.2787(3) 0.8502(3) 0.2822(3) 0.0356(9) Uani 1 1 d . . . . .
H34 H 0.2306 0.8198 0.2387 0.043 Uiso 1 1 calc R U . . .
C34A C 0.3773(3) 0.8587(3) 0.2563(3) 0.0309(8) Uani 1 1 d . . . . .
C35A C 0.4987(3) 0.8375(3) 0.1359(3) 0.0299(8) Uani 1 1 d . . . . .
C35 C 0.3528(3) 0.7360(3) 0.1232(3) 0.0360(9) Uani 1 1 d . . . . .
H35A H 0.3179 0.7033 0.1755 0.043 Uiso 1 1 calc R U . . .
H35B H 0.4023 0.6914 0.0988 0.043 Uiso 1 1 calc R U . . .
C36A C 0.6407(3) 0.8255(3) 0.0705(3) 0.0325(8) Uani 1 1 d . . . . .
C37 C 0.7162(3) 0.7930(3) 0.0144(3) 0.0395(9) Uani 1 1 d . . . . .
H37 H 0.7069 0.7392 -0.0270 0.047 Uiso 1 1 calc R U . . .
C38 C 0.8064(3) 0.8424(4) 0.0210(3) 0.0467(11) Uani 1 1 d . . . . .
H38 H 0.8598 0.8217 -0.0161 0.056 Uiso 1 1 calc R U . . .
C39 C 0.8189(3) 0.9209(4) 0.0809(4) 0.0489(12) Uani 1 1 d . . . . .
H39 H 0.8808 0.9535 0.0839 0.059 Uiso 1 1 calc R U . . .
C40 C 0.7425(3) 0.9532(3) 0.1371(3) 0.0414(10) Uani 1 1 d . . . . .
H40 H 0.7516 1.0073 0.1779 0.050 Uiso 1 1 calc R U . . .
C40A C 0.6530(3) 0.9043(3) 0.1318(3) 0.0333(8) Uani 1 1 d . . . . .
C40B C 0.5551(3) 0.9225(3) 0.1780(3) 0.0312(8) Uani 1 1 d . . . . .
C41 C 0.5565(3) 0.9132(3) 0.2912(3) 0.0289(8) Uani 1 1 d . . . . .
H41 H 0.5904 0.8522 0.3094 0.035 Uiso 1 1 calc R U . . .
C42 C 0.7588(3) 1.0676(3) 0.4601(3) 0.0321(8) Uani 1 1 d . . . . .
C43 C 0.7972(3) 1.1098(3) 0.3668(3) 0.0434(10) Uani 1 1 d . . . . .
H43A H 0.7407 1.1295 0.3225 0.052 Uiso 1 1 calc R U . . .
H43B H 0.8365 1.0625 0.3338 0.052 Uiso 1 1 calc R U . . .
H43C H 0.8392 1.1647 0.3841 0.052 Uiso 1 1 calc R U . . .
C44 C 0.8462(3) 1.0400(3) 0.5325(4) 0.0432(10) Uani 1 1 d . . . . .
H44A H 0.8207 1.0078 0.5895 0.052 Uiso 1 1 calc R U . . .
H44B H 0.8826 1.0969 0.5547 0.052 Uiso 1 1 calc R U . . .
H44C H 0.8913 0.9977 0.4996 0.052 Uiso 1 1 calc R U . . .
C45 C 0.6888(3) 1.1339(3) 0.5102(3) 0.0401(9) Uani 1 1 d . . . . .
H45A H 0.7258 1.1897 0.5346 0.048 Uiso 1 1 calc R U . . .
H45B H 0.6606 1.1013 0.5657 0.048 Uiso 1 1 calc R U . . .
H45C H 0.6348 1.1535 0.4627 0.048 Uiso 1 1 calc R U . . .
C46 C 0.2774(3) 0.7592(3) 0.0391(3) 0.0364(9) Uani 1 1 d . . . . .
C47 C 0.2359(3) 0.8482(4) 0.0270(4) 0.0458(11) Uani 1 1 d . . . . .
H47 H 0.2565 0.8978 0.0708 0.055 Uiso 1 1 calc R U . . .
C48 C 0.1635(4) 0.8652(4) -0.0498(4) 0.0559(13) Uani 1 1 d . . . . .
H48 H 0.1361 0.9267 -0.0589 0.067 Uiso 1 1 calc R U . . .
C49 C 0.1322(4) 0.7936(4) -0.1118(4) 0.0577(13) Uani 1 1 d . . . . .
H49 H 0.0822 0.8052 -0.1631 0.069 Uiso 1 1 calc R U . . .
C50 C 0.1727(3) 0.7047(4) -0.1004(4) 0.0515(12) Uani 1 1 d . . . . .
H50 H 0.1508 0.6551 -0.1436 0.062 Uiso 1 1 calc R U . . .
C51 C 0.2453(3) 0.6877(3) -0.0257(3) 0.0417(10) Uani 1 1 d . . . . .
H51 H 0.2736 0.6265 -0.0185 0.050 Uiso 1 1 calc R U . . .
C52 C 0.5077(3) 1.0168(3) 0.1423(3) 0.0366(9) Uani 1 1 d . . . . .
H52A H 0.4465 1.0276 0.1777 0.044 Uiso 1 1 calc R U . . .
H52B H 0.5548 1.0687 0.1605 0.044 Uiso 1 1 calc R U . . .
C53 C 0.4817(4) 1.0216(3) 0.0346(3) 0.0426(10) Uani 1 1 d . . . . .
H53 H 0.5324 1.0077 -0.0088 0.051 Uiso 1 1 calc R U . . .
C54 C 0.3925(4) 1.0439(4) -0.0044(4) 0.0563(13) Uani 1 1 d . . . . .
H54A H 0.3402 1.0582 0.0370 0.068 Uiso 1 1 calc R U . . .
H54B H 0.3805 1.0458 -0.0741 0.068 Uiso 1 1 calc R U . . .
H11N H 0.634(4) 0.807(2) 0.593(3) 0.047(13) Uiso 1 1 d D . . . .
H41N H 0.578(3) 1.0476(19) 0.350(4) 0.047(14) 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
S11 O11 1.495(3) . ?
S11 N11 1.664(3) . ?
S11 C12 1.843(4) . ?
S41 O41 1.496(3) . ?
S41 N41 1.658(3) . ?
S41 C42 1.848(4) . ?
N5 C5A 1.367(5) . ?
N5 C4A 1.426(5) . ?
N5 C5 1.462(5) . ?
N6 C5A 1.290(5) . ?
N6 C6A 1.435(5) . ?
N11 C11 1.467(5) . ?
N11 H11N 0.977(7) . ?
N35 C35A 1.373(5) . ?
N35 C34A 1.422(5) . ?
N35 C35 1.460(5) . ?
N36 C35A 1.295(5) . ?
N36 C36A 1.422(5) . ?
N41 C41 1.463(5) . ?
N41 H41N 0.979(7) . ?
C1 C2 1.382(6) . ?
C1 C1A 1.394(5) . ?
C1 H1 0.9500 . ?
C1A C4A 1.417(5) . ?
C1A C11 1.525(5) . ?
C2 C3 1.392(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(6) . ?
C3 H3 0.9500 . ?
C4 C4A 1.406(6) . ?
C4 H4 0.9500 . ?
C5 C16 1.518(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5A C10B 1.531(5) . ?
C6A C7 1.377(6) . ?
C6A C10A 1.399(6) . ?
C7 C8 1.395(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(6) . ?
C9 H9 0.9500 . ?
C10 C10A 1.380(5) . ?
C10 H10 0.9500 . ?
C10A C10B 1.511(5) . ?
C10B C11 1.543(5) . ?
C10B C22 1.546(6) . ?
C11 H11 1.0000 . ?
C12 C15 1.516(6) . ?
C12 C13 1.528(6) . ?
C12 C14 1.537(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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 C17 1.370(8) . ?
C16 C21 1.395(6) . ?
C17 C18 1.396(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(8) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.508(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.318(6) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9500 . ?
C24 H24B 0.9500 . ?
C31 C31A 1.391(5) . ?
C31 C32 1.403(5) . ?
C31 H31 0.9500 . ?
C31A C34A 1.415(6) . ?
C31A C41 1.527(5) . ?
C32 C33 1.373(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(6) . ?
C33 H33 0.9500 . ?
C34 C34A 1.397(5) . ?
C34 H34 0.9500 . ?
C35A C40B 1.515(5) . ?
C35 C46 1.513(6) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36A C37 1.386(6) . ?
C36A C40A 1.396(6) . ?
C37 C38 1.398(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.381(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.395(6) . ?
C39 H39 0.9500 . ?
C40 C40A 1.385(6) . ?
C40 H40 0.9500 . ?
C40A C40B 1.516(5) . ?
C40B C41 1.541(5) . ?
C40B C52 1.545(6) . ?
C41 H41 1.0000 . ?
C42 C43 1.520(6) . ?
C42 C45 1.520(6) . ?
C42 C44 1.534(6) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 C47 1.384(7) . ?
C46 C51 1.392(6) . ?
C47 C48 1.401(7) . ?
C47 H47 0.9500 . ?
C48 C49 1.368(8) . ?
C48 H48 0.9500 . ?
C49 C50 1.376(8) . ?
C49 H49 0.9500 . ?
C50 C51 1.383(7) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 C53 1.484(6) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.317(8) . ?
C53 H53 0.9500 . ?
C54 H54A 0.9500 . ?
C54 H54B 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
O11 S11 N11 111.01(16) . . ?
O11 S11 C12 104.13(17) . . ?
N11 S11 C12 99.60(17) . . ?
O41 S41 N41 111.48(15) . . ?
O41 S41 C42 104.33(17) . . ?
N41 S41 C42 99.93(17) . . ?
C5A N5 C4A 117.6(3) . . ?
C5A N5 C5 118.2(3) . . ?
C4A N5 C5 120.2(3) . . ?
C5A N6 C6A 105.3(3) . . ?
C11 N11 S11 115.0(3) . . ?
C11 N11 H11N 111(3) . . ?
S11 N11 H11N 121(3) . . ?
C35A N35 C34A 118.5(3) . . ?
C35A N35 C35 118.0(3) . . ?
C34A N35 C35 121.4(3) . . ?
C35A N36 C36A 105.3(3) . . ?
C41 N41 S41 115.5(3) . . ?
C41 N41 H41N 115(3) . . ?
S41 N41 H41N 119(3) . . ?
C2 C1 C1A 121.7(4) . . ?
C2 C1 H1 119.1 . . ?
C1A C1 H1 119.1 . . ?
C1 C1A C4A 118.4(4) . . ?
C1 C1A C11 120.0(3) . . ?
C4A C1A C11 121.4(3) . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C4A 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C4A C4 H4 119.8 . . ?
C4 C4A C1A 119.5(3) . . ?
C4 C4A N5 119.1(3) . . ?
C1A C4A N5 121.4(3) . . ?
N5 C5 C16 114.8(4) . . ?
N5 C5 H5A 108.6 . . ?
C16 C5 H5A 108.6 . . ?
N5 C5 H5B 108.6 . . ?
C16 C5 H5B 108.6 . . ?
H5A C5 H5B 107.5 . . ?
N6 C5A N5 125.5(3) . . ?
N6 C5A C10B 115.7(3) . . ?
N5 C5A C10B 118.7(3) . . ?
C7 C6A C10A 121.1(4) . . ?
C7 C6A N6 126.2(4) . . ?
C10A C6A N6 112.6(3) . . ?
C6A C7 C8 117.9(4) . . ?
C6A C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C10A C10 C9 118.0(4) . . ?
C10A C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C10 C10A C6A 121.2(4) . . ?
C10 C10A C10B 131.9(4) . . ?
C6A C10A C10B 106.9(3) . . ?
C10A C10B C5A 99.1(3) . . ?
C10A C10B C11 113.5(3) . . ?
C5A C10B C11 108.8(3) . . ?
C10A C10B C22 112.4(3) . . ?
C5A C10B C22 109.9(3) . . ?
C11 C10B C22 112.3(3) . . ?
N11 C11 C1A 113.0(3) . . ?
N11 C11 C10B 111.6(3) . . ?
C1A C11 C10B 109.8(3) . . ?
N11 C11 H11 107.4 . . ?
C1A C11 H11 107.4 . . ?
C10B C11 H11 107.4 . . ?
C15 C12 C13 112.2(4) . . ?
C15 C12 C14 110.5(3) . . ?
C13 C12 C14 111.2(3) . . ?
C15 C12 S11 109.5(3) . . ?
C13 C12 S11 109.9(3) . . ?
C14 C12 S11 103.2(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.4(4) . . ?
C17 C16 C5 123.7(4) . . ?
C21 C16 C5 117.9(4) . . ?
C16 C17 C18 121.1(5) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 120.5(6) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 118.4(5) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C21 121.2(5) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 120.3(5) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C23 C22 C10B 113.0(3) . . ?
C23 C22 H22A 109.0 . . ?
C10B C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C10B C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 125.4(4) . . ?
C24 C23 H23 117.3 . . ?
C22 C23 H23 117.3 . . ?
C23 C24 H24A 120.0 . . ?
C23 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
C31A C31 C32 121.1(4) . . ?
C31A C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C31 C31A C34A 118.2(3) . . ?
C31 C31A C41 122.0(3) . . ?
C34A C31A C41 119.7(3) . . ?
C33 C32 C31 119.8(4) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 120.7(3) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C34A 119.9(4) . . ?
C33 C34 H34 120.0 . . ?
C34A C34 H34 120.0 . . ?
C34 C34A C31A 120.3(3) . . ?
C34 C34A N35 119.4(4) . . ?
C31A C34A N35 120.2(3) . . ?
N36 C35A N35 123.6(4) . . ?
N36 C35A C40B 116.9(3) . . ?
N35 C35A C40B 119.4(3) . . ?
N35 C35 C46 115.0(3) . . ?
N35 C35 H35A 108.5 . . ?
C46 C35 H35A 108.5 . . ?
N35 C35 H35B 108.5 . . ?
C46 C35 H35B 108.5 . . ?
H35A C35 H35B 107.5 . . ?
C37 C36A C40A 122.0(4) . . ?
C37 C36A N36 126.1(4) . . ?
C40A C36A N36 111.8(3) . . ?
C36A C37 C38 117.4(4) . . ?
C36A C37 H37 121.3 . . ?
C38 C37 H37 121.3 . . ?
C39 C38 C37 120.9(4) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C38 C39 C40 121.3(4) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C40A C40 C39 118.4(4) . . ?
C40A C40 H40 120.8 . . ?
C39 C40 H40 120.8 . . ?
C40 C40A C36A 120.0(4) . . ?
C40 C40A C40B 131.9(4) . . ?
C36A C40A C40B 108.0(3) . . ?
C35A C40B C40A 97.7(3) . . ?
C35A C40B C41 106.5(3) . . ?
C40A C40B C41 116.2(3) . . ?
C35A C40B C52 112.5(3) . . ?
C40A C40B C52 111.6(3) . . ?
C41 C40B C52 111.4(3) . . ?
N41 C41 C31A 114.5(3) . . ?
N41 C41 C40B 112.1(3) . . ?
C31A C41 C40B 108.0(3) . . ?
N41 C41 H41 107.3 . . ?
C31A C41 H41 107.3 . . ?
C40B C41 H41 107.3 . . ?
C43 C42 C45 112.5(4) . . ?
C43 C42 C44 110.3(3) . . ?
C45 C42 C44 109.9(3) . . ?
C43 C42 S41 109.5(3) . . ?
C45 C42 S41 110.5(3) . . ?
C44 C42 S41 103.6(3) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 C51 118.8(4) . . ?
C47 C46 C35 122.2(4) . . ?
C51 C46 C35 119.0(4) . . ?
C46 C47 C48 120.0(5) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C49 C48 C47 120.2(5) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C48 C49 C50 120.3(5) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C49 C50 C51 119.8(5) . . ?
C49 C50 H50 120.1 . . ?
C51 C50 H50 120.1 . . ?
C50 C51 C46 120.9(5) . . ?
C50 C51 H51 119.6 . . ?
C46 C51 H51 119.6 . . ?
C53 C52 C40B 114.5(3) . . ?
C53 C52 H52A 108.6 . . ?
C40B C52 H52A 108.6 . . ?
C53 C52 H52B 108.6 . . ?
C40B C52 H52B 108.6 . . ?
H52A C52 H52B 107.6 . . ?
C54 C53 C52 124.0(5) . . ?
C54 C53 H53 118.0 . . ?
C52 C53 H53 118.0 . . ?
C53 C54 H54A 120.0 . . ?
C53 C54 H54B 120.0 . . ?
H54A C54 H54B 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
O11 S11 N11 C11 -64.7(3) . . . . ?
C12 S11 N11 C11 -174.0(3) . . . . ?
O41 S41 N41 C41 -76.6(3) . . . . ?
C42 S41 N41 C41 173.6(3) . . . . ?
C2 C1 C1A C4A -0.6(6) . . . . ?
C2 C1 C1A C11 -175.3(4) . . . . ?
C1A C1 C2 C3 -2.1(6) . . . . ?
C1 C2 C3 C4 2.4(6) . . . . ?
C2 C3 C4 C4A -0.1(6) . . . . ?
C3 C4 C4A C1A -2.6(6) . . . . ?
C3 C4 C4A N5 173.3(4) . . . . ?
C1 C1A C4A C4 3.0(6) . . . . ?
C11 C1A C4A C4 177.6(4) . . . . ?
C1 C1A C4A N5 -172.9(4) . . . . ?
C11 C1A C4A N5 1.7(6) . . . . ?
C5A N5 C4A C4 -175.0(4) . . . . ?
C5 N5 C4A C4 -18.2(5) . . . . ?
C5A N5 C4A C1A 0.8(5) . . . . ?
C5 N5 C4A C1A 157.7(4) . . . . ?
C5A N5 C5 C16 -119.1(4) . . . . ?
C4A N5 C5 C16 84.2(4) . . . . ?
C6A N6 C5A N5 -173.6(3) . . . . ?
C6A N6 C5A C10B 6.0(4) . . . . ?
C4A N5 C5A N6 149.4(4) . . . . ?
C5 N5 C5A N6 -7.9(6) . . . . ?
C4A N5 C5A C10B -30.2(5) . . . . ?
C5 N5 C5A C10B 172.5(3) . . . . ?
C5A N6 C6A C7 173.5(4) . . . . ?
C5A N6 C6A C10A -2.7(4) . . . . ?
C10A C6A C7 C8 0.3(6) . . . . ?
N6 C6A C7 C8 -175.6(4) . . . . ?
C6A C7 C8 C9 -1.3(7) . . . . ?
C7 C8 C9 C10 0.8(7) . . . . ?
C8 C9 C10 C10A 0.8(6) . . . . ?
C9 C10 C10A C6A -1.8(6) . . . . ?
C9 C10 C10A C10B 177.1(4) . . . . ?
C7 C6A C10A C10 1.3(6) . . . . ?
N6 C6A C10A C10 177.7(3) . . . . ?
C7 C6A C10A C10B -177.9(4) . . . . ?
N6 C6A C10A C10B -1.5(4) . . . . ?
C10 C10A C10B C5A -174.7(4) . . . . ?
C6A C10A C10B C5A 4.3(4) . . . . ?
C10 C10A C10B C11 -59.6(5) . . . . ?
C6A C10A C10B C11 119.4(3) . . . . ?
C10 C10A C10B C22 69.2(5) . . . . ?
C6A C10A C10B C22 -111.7(3) . . . . ?
N6 C5A C10B C10A -6.7(4) . . . . ?
N5 C5A C10B C10A 173.0(3) . . . . ?
N6 C5A C10B C11 -125.4(4) . . . . ?
N5 C5A C10B C11 54.3(4) . . . . ?
N6 C5A C10B C22 111.3(4) . . . . ?
N5 C5A C10B C22 -69.0(4) . . . . ?
S11 N11 C11 C1A 111.9(3) . . . . ?
S11 N11 C11 C10B -123.7(3) . . . . ?
C1 C1A C11 N11 -37.0(5) . . . . ?
C4A C1A C11 N11 148.4(4) . . . . ?
C1 C1A C11 C10B -162.4(4) . . . . ?
C4A C1A C11 C10B 23.0(5) . . . . ?
C10A C10B C11 N11 77.9(4) . . . . ?
C5A C10B C11 N11 -172.8(3) . . . . ?
C22 C10B C11 N11 -51.0(4) . . . . ?
C10A C10B C11 C1A -155.9(3) . . . . ?
C5A C10B C11 C1A -46.7(4) . . . . ?
C22 C10B C11 C1A 75.2(4) . . . . ?
O11 S11 C12 C15 -45.8(3) . . . . ?
N11 S11 C12 C15 68.9(3) . . . . ?
O11 S11 C12 C13 -169.5(3) . . . . ?
N11 S11 C12 C13 -54.8(3) . . . . ?
O11 S11 C12 C14 71.9(3) . . . . ?
N11 S11 C12 C14 -173.5(3) . . . . ?
N5 C5 C16 C17 -0.1(6) . . . . ?
N5 C5 C16 C21 179.7(4) . . . . ?
C21 C16 C17 C18 0.6(8) . . . . ?
C5 C16 C17 C18 -179.6(4) . . . . ?
C16 C17 C18 C19 -0.8(8) . . . . ?
C17 C18 C19 C20 1.0(9) . . . . ?
C18 C19 C20 C21 -1.1(9) . . . . ?
C19 C20 C21 C16 0.9(8) . . . . ?
C17 C16 C21 C20 -0.7(7) . . . . ?
C5 C16 C21 C20 179.5(4) . . . . ?
C10A C10B C22 C23 53.3(4) . . . . ?
C5A C10B C22 C23 -56.0(4) . . . . ?
C11 C10B C22 C23 -177.2(3) . . . . ?
C10B C22 C23 C24 125.9(5) . . . . ?
C32 C31 C31A C34A 0.5(6) . . . . ?
C32 C31 C31A C41 -177.8(4) . . . . ?
C31A C31 C32 C33 -1.9(6) . . . . ?
C31 C32 C33 C34 1.8(6) . . . . ?
C32 C33 C34 C34A -0.3(6) . . . . ?
C33 C34 C34A C31A -1.2(6) . . . . ?
C33 C34 C34A N35 176.6(4) . . . . ?
C31 C31A C34A C34 1.0(6) . . . . ?
C41 C31A C34A C34 179.4(4) . . . . ?
C31 C31A C34A N35 -176.8(3) . . . . ?
C41 C31A C34A N35 1.6(5) . . . . ?
C35A N35 C34A C34 170.8(4) . . . . ?
C35 N35 C34A C34 -26.0(5) . . . . ?
C35A N35 C34A C31A -11.4(5) . . . . ?
C35 N35 C34A C31A 151.8(4) . . . . ?
C36A N36 C35A N35 -173.7(4) . . . . ?
C36A N36 C35A C40B 4.0(4) . . . . ?
C34A N35 C35A N36 160.0(4) . . . . ?
C35 N35 C35A N36 -3.8(6) . . . . ?
C34A N35 C35A C40B -17.6(5) . . . . ?
C35 N35 C35A C40B 178.6(3) . . . . ?
C35A N35 C35 C46 -97.2(4) . . . . ?
C34A N35 C35 C46 99.5(4) . . . . ?
C35A N36 C36A C37 179.3(4) . . . . ?
C35A N36 C36A C40A -0.9(4) . . . . ?
C40A C36A C37 C38 -0.2(6) . . . . ?
N36 C36A C37 C38 179.6(4) . . . . ?
C36A C37 C38 C39 -0.4(7) . . . . ?
C37 C38 C39 C40 0.4(8) . . . . ?
C38 C39 C40 C40A 0.2(8) . . . . ?
C39 C40 C40A C36A -0.8(7) . . . . ?
C39 C40 C40A C40B -176.6(5) . . . . ?
C37 C36A C40A C40 0.8(6) . . . . ?
N36 C36A C40A C40 -179.1(4) . . . . ?
C37 C36A C40A C40B 177.5(4) . . . . ?
N36 C36A C40A C40B -2.4(4) . . . . ?
N36 C35A C40B C40A -5.1(4) . . . . ?
N35 C35A C40B C40A 172.6(3) . . . . ?
N36 C35A C40B C41 -125.5(4) . . . . ?
N35 C35A C40B C41 52.3(4) . . . . ?
N36 C35A C40B C52 112.2(4) . . . . ?
N35 C35A C40B C52 -70.1(4) . . . . ?
C40 C40A C40B C35A -179.8(5) . . . . ?
C36A C40A C40B C35A 4.0(4) . . . . ?
C40 C40A C40B C41 -67.1(6) . . . . ?
C36A C40A C40B C41 116.7(4) . . . . ?
C40 C40A C40B C52 62.2(6) . . . . ?
C36A C40A C40B C52 -114.0(4) . . . . ?
S41 N41 C41 C31A 104.9(3) . . . . ?
S41 N41 C41 C40B -131.5(3) . . . . ?
C31 C31A C41 N41 -22.4(5) . . . . ?
C34A C31A C41 N41 159.3(3) . . . . ?
C31 C31A C41 C40B -148.1(4) . . . . ?
C34A C31A C41 C40B 33.6(5) . . . . ?
C35A C40B C41 N41 176.7(3) . . . . ?
C40A C40B C41 N41 69.1(4) . . . . ?
C52 C40B C41 N41 -60.2(4) . . . . ?
C35A C40B C41 C31A -56.2(4) . . . . ?
C40A C40B C41 C31A -163.7(3) . . . . ?
C52 C40B C41 C31A 66.9(4) . . . . ?
O41 S41 C42 C43 -170.2(3) . . . . ?
N41 S41 C42 C43 -54.8(3) . . . . ?
O41 S41 C42 C45 -45.7(3) . . . . ?
N41 S41 C42 C45 69.7(3) . . . . ?
O41 S41 C42 C44 72.1(3) . . . . ?
N41 S41 C42 C44 -172.6(3) . . . . ?
N35 C35 C46 C47 -21.9(5) . . . . ?
N35 C35 C46 C51 161.0(4) . . . . ?
C51 C46 C47 C48 -0.4(7) . . . . ?
C35 C46 C47 C48 -177.5(4) . . . . ?
C46 C47 C48 C49 1.3(8) . . . . ?
C47 C48 C49 C50 -1.1(8) . . . . ?
C48 C49 C50 C51 0.1(8) . . . . ?
C49 C50 C51 C46 0.7(7) . . . . ?
C47 C46 C51 C50 -0.6(6) . . . . ?
C35 C46 C51 C50 176.6(4) . . . . ?
C35A C40B C52 C53 -46.7(5) . . . . ?
C40A C40B C52 C53 62.0(5) . . . . ?
C41 C40B C52 C53 -166.2(4) . . . . ?
C40B C52 C53 C54 126.4(5) . . . . ?

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


