# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_tcd248
_database_code_depnum_ccdc_archive 'CCDC 1415369'
_audit_update_record             
;
2015-07-27 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H44 N3, F6 P'
_chemical_formula_sum            'C36 H44 F6 N3 P'
_chemical_formula_weight         663.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.9164(3)
_cell_length_b                   16.2651(4)
_cell_length_c                   19.0039(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.2134(9)
_cell_angle_gamma                90
_cell_volume                     3368.96(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9805
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.38

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7183
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker, 2014)'

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.258
_diffrn_reflns_number            122896
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.649
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6919
_reflns_number_gt                6244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker-AXS, 2008-2014)'
_computing_publication_material  'SHELXTL (Bruker-AXS, 2008-2014)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+2.8317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6919
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.23107(14) 0.58765(10) 0.68575(8) 0.0219(3) Uani 1 1 d . . . . .
H1A H 0.2164 0.5377 0.6576 0.033 Uiso 1 1 calc R U . . .
H1B H 0.3196 0.5957 0.6946 0.033 Uiso 1 1 calc R U . . .
H1C H 0.1961 0.6351 0.6600 0.033 Uiso 1 1 calc R U . . .
C2 C 0.17051(14) 0.57894(9) 0.75593(8) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.03044(14) 0.56617(10) 0.74329(9) 0.0270(3) Uani 1 1 d . . . . .
H3A H -0.0061 0.5594 0.7894 0.032 Uiso 1 1 calc R U . . .
H3B H -0.0056 0.6162 0.7209 0.032 Uiso 1 1 calc R U . . .
C5 C -0.05260(16) 0.51957(11) 0.62825(9) 0.0297(4) Uani 1 1 d . . . . .
H5A H 0.0031 0.5606 0.6086 0.036 Uiso 1 1 calc R U . . .
H5B H -0.1336 0.5460 0.6325 0.036 Uiso 1 1 calc R U . . .
C6 C -0.06639(15) 0.44738(11) 0.57858(9) 0.0277(3) Uani 1 1 d . . . . .
C7 C 0.02683(17) 0.38943(12) 0.57445(10) 0.0324(4) Uani 1 1 d . . . . .
H7 H 0.1013 0.3966 0.6021 0.039 Uiso 1 1 calc R U . . .
C8 C 0.01263(18) 0.32150(12) 0.53067(10) 0.0364(4) Uani 1 1 d . . . . .
H8 H 0.0768 0.2823 0.5288 0.044 Uiso 1 1 calc R U . . .
C9 C -0.09548(18) 0.31074(12) 0.48949(10) 0.0357(4) Uani 1 1 d . . . . .
H9 H -0.1056 0.2642 0.4596 0.043 Uiso 1 1 calc R U . . .
C10 C -0.18784(17) 0.36820(13) 0.49240(9) 0.0348(4) Uani 1 1 d . . . . .
H10 H -0.2618 0.3613 0.4642 0.042 Uiso 1 1 calc R U . . .
C11 C -0.17338(16) 0.43612(12) 0.53624(9) 0.0304(4) Uani 1 1 d . . . . .
H11 H -0.2374 0.4755 0.5374 0.036 Uiso 1 1 calc R U . . .
C12 C -0.08800(16) 0.43769(11) 0.73291(10) 0.0304(4) Uani 1 1 d . . . . .
H12A H -0.1286 0.4013 0.6969 0.036 Uiso 1 1 calc R U . . .
H12B H -0.1523 0.4698 0.7552 0.036 Uiso 1 1 calc R U . . .
C13 C -0.01893(16) 0.38604(11) 0.78815(10) 0.0309(4) Uani 1 1 d . . . . .
C14 C 0.05810(17) 0.32354(11) 0.76730(10) 0.0334(4) Uani 1 1 d . . . . .
H14 H 0.0595 0.3098 0.7188 0.040 Uiso 1 1 calc R U . . .
C15 C 0.13307(19) 0.28087(12) 0.81619(11) 0.0406(4) Uani 1 1 d . . . . .
H15 H 0.1850 0.2382 0.8011 0.049 Uiso 1 1 calc R U . . .
C16 C 0.1319(2) 0.30068(14) 0.88710(12) 0.0453(5) Uani 1 1 d . . . . .
H16 H 0.1855 0.2732 0.9205 0.054 Uiso 1 1 calc R U . . .
C17 C 0.0529(2) 0.36030(14) 0.90916(11) 0.0430(5) Uani 1 1 d . . . . .
H17 H 0.0504 0.3726 0.9579 0.052 Uiso 1 1 calc R U . . .
C18 C -0.02353(18) 0.40279(12) 0.86014(10) 0.0364(4) Uani 1 1 d . . . . .
H18 H -0.0788 0.4431 0.8758 0.044 Uiso 1 1 calc R U . . .
C19 C 0.22013(14) 0.50217(10) 0.79526(8) 0.0234(3) Uani 1 1 d . . . . .
H19A H 0.1666 0.4901 0.8344 0.028 Uiso 1 1 calc R U . . .
H19B H 0.2147 0.4548 0.7625 0.028 Uiso 1 1 calc R U . . .
C21 C 0.43353(17) 0.44089(11) 0.80195(10) 0.0317(4) Uani 1 1 d . . . . .
H21A H 0.5160 0.4476 0.8256 0.038 Uiso 1 1 calc R U . . .
H21B H 0.4000 0.3877 0.8173 0.038 Uiso 1 1 calc R U . . .
C22 C 0.44580(15) 0.43847(10) 0.72386(9) 0.0281(4) Uani 1 1 d . . . . .
C23 C 0.37629(16) 0.38412(10) 0.68088(9) 0.0281(4) Uani 1 1 d . . . . .
H23 H 0.3197 0.3480 0.7013 0.034 Uiso 1 1 calc R U . . .
C24 C 0.38921(17) 0.38245(11) 0.60882(10) 0.0327(4) Uani 1 1 d . . . . .
H24 H 0.3417 0.3453 0.5799 0.039 Uiso 1 1 calc R U . . .
C25 C 0.4714(2) 0.43494(13) 0.57900(11) 0.0420(5) Uani 1 1 d . . . . .
H25 H 0.4804 0.4340 0.5296 0.050 Uiso 1 1 calc R U . . .
C26 C 0.5409(2) 0.48899(13) 0.62131(12) 0.0463(5) Uani 1 1 d . . . . .
H26 H 0.5967 0.5253 0.6006 0.056 Uiso 1 1 calc R U . . .
C27 C 0.52928(17) 0.49027(12) 0.69345(11) 0.0368(4) Uani 1 1 d . . . . .
H27 H 0.5784 0.5266 0.7222 0.044 Uiso 1 1 calc R U . . .
C28 C 0.18680(14) 0.65938(10) 0.79887(9) 0.0248(3) Uani 1 1 d . . . . .
H28A H 0.1634 0.7064 0.7679 0.030 Uiso 1 1 calc R U . . .
H28B H 0.1300 0.6585 0.8377 0.030 Uiso 1 1 calc R U . . .
C30 C 0.36527(16) 0.75295(10) 0.80880(9) 0.0289(4) Uani 1 1 d . . . . .
H30A H 0.4397 0.7645 0.8394 0.035 Uiso 1 1 calc R U . . .
H30B H 0.3047 0.7967 0.8170 0.035 Uiso 1 1 calc R U . . .
C31 C 0.39805(15) 0.75587(10) 0.73288(9) 0.0256(3) Uani 1 1 d . . . . .
C32 C 0.50362(15) 0.71651(10) 0.71189(9) 0.0267(3) Uani 1 1 d . . . . .
H32 H 0.5552 0.6883 0.7458 0.032 Uiso 1 1 calc R U . . .
C33 C 0.53385(18) 0.71818(12) 0.64195(10) 0.0345(4) Uani 1 1 d . . . . .
H33 H 0.6056 0.6909 0.6282 0.041 Uiso 1 1 calc R U . . .
C34 C 0.4593(2) 0.75982(13) 0.59181(10) 0.0430(5) Uani 1 1 d . . . . .
H34 H 0.4796 0.7607 0.5439 0.052 Uiso 1 1 calc R U . . .
C35 C 0.3557(2) 0.79967(12) 0.61242(11) 0.0435(5) Uani 1 1 d . . . . .
H35 H 0.3049 0.8284 0.5785 0.052 Uiso 1 1 calc R U . . .
C36 C 0.32534(17) 0.79813(11) 0.68211(11) 0.0347(4) Uani 1 1 d . . . . .
H36 H 0.2540 0.8262 0.6956 0.042 Uiso 1 1 calc R U . . .
C37 C 0.31945(18) 0.66645(12) 0.90727(9) 0.0326(4) Uani 1 1 d . . . . .
H37A H 0.2645 0.7083 0.9264 0.039 Uiso 1 1 calc R U . . .
H37B H 0.4041 0.6785 0.9257 0.039 Uiso 1 1 calc R U . . .
C38 C 0.28223(19) 0.58170(13) 0.93283(9) 0.0377(4) Uani 1 1 d . . . . .
H38A H 0.2900 0.5809 0.9850 0.045 Uiso 1 1 calc R U . . .
H38B H 0.1948 0.5723 0.9183 0.045 Uiso 1 1 calc R U . . .
C39 C 0.35773(19) 0.51202(12) 0.90503(9) 0.0347(4) Uani 1 1 d . . . . .
H39A H 0.3275 0.4592 0.9233 0.042 Uiso 1 1 calc R U . . .
H39B H 0.4443 0.5186 0.9226 0.042 Uiso 1 1 calc R U . . .
F1 F 0.58393(11) 0.62040(10) 0.86118(7) 0.0594(4) Uani 1 1 d . . . . .
F2 F 0.86868(12) 0.60497(9) 0.91029(8) 0.0563(4) Uani 1 1 d . . . . .
F3A F 0.7145(2) 0.51173(16) 0.88665(19) 0.0480(7) Uani 0.5 1 d . . P A 1
F4A F 0.6869(4) 0.6132(3) 0.96387(16) 0.0661(11) Uani 0.5 1 d . . P B 1
F5A F 0.7339(5) 0.7078(3) 0.8797(4) 0.0644(19) Uani 0.5 1 d . . P B 1
F6A F 0.7580(3) 0.6039(2) 0.80333(18) 0.0388(8) Uani 0.5 1 d . . P B 1
F3B F 0.6995(5) 0.5296(4) 0.9195(3) 0.0737(11) Uani 0.42 1 d . . P B 2
F4B F 0.7030(6) 0.6544(4) 0.9641(3) 0.0737(11) Uani 0.42 1 d . . P B 2
F5B F 0.7559(10) 0.7073(7) 0.8649(6) 0.0737(11) Uani 0.42 1 d . . P B 2
F6B F 0.7543(8) 0.5831(5) 0.8157(4) 0.0737(11) Uani 0.42 1 d . . P B 2
F3C F 0.6870(12) 0.5523(11) 0.9471(8) 0.0278(15) Uiso 0.08 1 d . . P B 3
F4C F 0.7250(12) 0.6901(9) 0.9549(7) 0.0278(15) Uiso 0.08 1 d . . P C 3
F5C F 0.7666(13) 0.6936(9) 0.8367(8) 0.0278(15) Uiso 0.08 1 d . . P B 3
F6C F 0.7402(12) 0.5513(9) 0.8323(8) 0.0278(15) Uiso 0.08 1 d . . P B 3
N4 N -0.00333(12) 0.49446(9) 0.69858(7) 0.0260(3) Uani 1 1 d . . . . .
N20 N 0.35156(13) 0.50937(9) 0.82525(7) 0.0245(3) Uani 1 1 d . . . . .
N29 N 0.31364(12) 0.67271(8) 0.82926(7) 0.0242(3) Uani 1 1 d . . . . .
P1 P 0.72693(4) 0.61443(3) 0.88690(3) 0.03412(13) Uani 1 1 d . . . . .
H20 H 0.3778(19) 0.5593(14) 0.8124(11) 0.031(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.528(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C19 1.538(2) . ?
C2 C28 1.547(2) . ?
C2 C3 1.548(2) . ?
C3 N4 1.478(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 N4 1.470(2) . ?
C5 C6 1.509(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.392(3) . ?
C6 C11 1.393(2) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 N4 1.483(2) . ?
C12 C13 1.512(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.391(3) . ?
C13 C18 1.399(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N20 1.518(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C22 1.498(3) . ?
C21 N20 1.511(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.390(3) . ?
C22 C23 1.398(2) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 N29 1.486(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C30 N29 1.482(2) . ?
C30 C31 1.506(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C36 1.396(2) . ?
C31 C32 1.396(2) . ?
C32 C33 1.388(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.394(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 N29 1.484(2) . ?
C37 C38 1.524(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.514(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 N20 1.514(2) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
F1 P1 1.6123(13) . ?
F2 P1 1.5933(13) . ?
F3A P1 1.676(3) . ?
F4A P1 1.550(3) . ?
F5A P1 1.527(6) . ?
F6A P1 1.652(4) . ?
F3B P1 1.549(5) . ?
F4B P1 1.639(6) . ?
F5B P1 1.604(11) . ?
F6B P1 1.492(9) . ?
F3C P1 1.605(14) . ?
F4C P1 1.786(14) . ?
F5C P1 1.675(15) . ?
F6C P1 1.473(14) . ?
N20 H20 0.90(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C19 109.97(12) . . ?
C1 C2 C28 109.84(13) . . ?
C19 C2 C28 113.79(13) . . ?
C1 C2 C3 110.42(13) . . ?
C19 C2 C3 106.51(13) . . ?
C28 C2 C3 106.17(12) . . ?
N4 C3 C2 114.05(13) . . ?
N4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
N4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N4 C5 C6 111.78(14) . . ?
N4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C11 118.06(16) . . ?
C7 C6 C5 120.96(15) . . ?
C11 C6 C5 120.98(16) . . ?
C8 C7 C6 121.04(17) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.06(18) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.47(17) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.34(17) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 121.01(17) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
N4 C12 C13 110.63(14) . . ?
N4 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C18 118.44(18) . . ?
C14 C13 C12 119.61(16) . . ?
C18 C13 C12 121.80(17) . . ?
C15 C14 C13 121.17(18) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.35(19) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.18(19) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
N20 C19 C2 114.79(12) . . ?
N20 C19 H19A 108.6 . . ?
C2 C19 H19A 108.6 . . ?
N20 C19 H19B 108.6 . . ?
C2 C19 H19B 108.6 . . ?
H19A C19 H19B 107.5 . . ?
C22 C21 N20 113.39(13) . . ?
C22 C21 H21A 108.9 . . ?
N20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
N20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C27 C22 C23 119.16(17) . . ?
C27 C22 C21 119.53(16) . . ?
C23 C22 C21 121.31(16) . . ?
C24 C23 C22 120.54(17) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.83(18) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.98(19) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 120.41(19) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C22 120.07(18) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
N29 C28 C2 113.92(13) . . ?
N29 C28 H28A 108.8 . . ?
C2 C28 H28A 108.8 . . ?
N29 C28 H28B 108.8 . . ?
C2 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
N29 C30 C31 113.16(13) . . ?
N29 C30 H30A 108.9 . . ?
C31 C30 H30A 108.9 . . ?
N29 C30 H30B 108.9 . . ?
C31 C30 H30B 108.9 . . ?
H30A C30 H30B 107.8 . . ?
C36 C31 C32 118.35(17) . . ?
C36 C31 C30 121.41(16) . . ?
C32 C31 C30 120.23(15) . . ?
C33 C32 C31 120.62(16) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 120.21(19) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C35 C34 C33 119.41(19) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C34 C35 C36 120.52(18) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C31 120.88(19) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
N29 C37 C38 112.53(14) . . ?
N29 C37 H37A 109.1 . . ?
C38 C37 H37A 109.1 . . ?
N29 C37 H37B 109.1 . . ?
C38 C37 H37B 109.1 . . ?
H37A C37 H37B 107.8 . . ?
C39 C38 C37 113.94(16) . . ?
C39 C38 H38A 108.8 . . ?
C37 C38 H38A 108.8 . . ?
C39 C38 H38B 108.8 . . ?
C37 C38 H38B 108.8 . . ?
H38A C38 H38B 107.7 . . ?
C38 C39 N20 112.09(15) . . ?
C38 C39 H39A 109.2 . . ?
N20 C39 H39A 109.2 . . ?
C38 C39 H39B 109.2 . . ?
N20 C39 H39B 109.2 . . ?
H39A C39 H39B 107.9 . . ?
C5 N4 C3 111.72(14) . . ?
C5 N4 C12 111.57(13) . . ?
C3 N4 C12 112.33(13) . . ?
C21 N20 C39 108.69(13) . . ?
C21 N20 C19 113.32(13) . . ?
C39 N20 C19 111.47(13) . . ?
C21 N20 H20 112.5(13) . . ?
C39 N20 H20 104.4(13) . . ?
C19 N20 H20 106.1(13) . . ?
C30 N29 C37 109.09(13) . . ?
C30 N29 C28 112.72(13) . . ?
C37 N29 C28 111.41(13) . . ?
F6B P1 F3B 96.4(4) . . ?
F5A P1 F4A 96.7(3) . . ?
F6C P1 F2 89.8(5) . . ?
F6B P1 F2 88.8(3) . . ?
F5A P1 F2 93.9(2) . . ?
F3B P1 F2 90.5(2) . . ?
F4A P1 F2 93.21(16) . . ?
F6B P1 F5B 91.9(5) . . ?
F3B P1 F5B 171.5(4) . . ?
F2 P1 F5B 87.8(4) . . ?
F6C P1 F3C 96.0(9) . . ?
F2 P1 F3C 92.2(5) . . ?
F6C P1 F1 87.7(5) . . ?
F6B P1 F1 89.1(3) . . ?
F5A P1 F1 88.0(2) . . ?
F3B P1 F1 88.3(2) . . ?
F4A P1 F1 88.15(16) . . ?
F2 P1 F1 177.49(9) . . ?
F5B P1 F1 93.8(4) . . ?
F3C P1 F1 87.5(5) . . ?
F6B P1 F4B 176.0(4) . . ?
F3B P1 F4B 87.2(3) . . ?
F2 P1 F4B 89.4(2) . . ?
F5B P1 F4B 84.4(4) . . ?
F1 P1 F4B 92.7(2) . . ?
F5A P1 F6A 90.2(3) . . ?
F4A P1 F6A 172.0(2) . . ?
F2 P1 F6A 90.55(13) . . ?
F1 P1 F6A 87.84(13) . . ?
F6C P1 F5C 95.5(7) . . ?
F2 P1 F5C 87.4(5) . . ?
F3C P1 F5C 168.5(8) . . ?
F1 P1 F5C 93.3(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
C1 C2 C3 N4 57.12(18) . . . . ?
C19 C2 C3 N4 -62.26(17) . . . . ?
C28 C2 C3 N4 176.14(14) . . . . ?
N4 C5 C6 C7 -45.4(2) . . . . ?
N4 C5 C6 C11 133.68(17) . . . . ?
C11 C6 C7 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 177.70(17) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C6 -0.6(3) . . . . ?
C7 C6 C11 C10 1.4(3) . . . . ?
C5 C6 C11 C10 -177.69(17) . . . . ?
N4 C12 C13 C14 -72.41(19) . . . . ?
N4 C12 C13 C18 103.15(18) . . . . ?
C18 C13 C14 C15 -2.8(3) . . . . ?
C12 C13 C14 C15 172.88(16) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 2.6(3) . . . . ?
C15 C16 C17 C18 -2.0(3) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C14 C13 C18 C17 3.4(3) . . . . ?
C12 C13 C18 C17 -172.18(16) . . . . ?
C1 C2 C19 N20 71.64(16) . . . . ?
C28 C2 C19 N20 -52.07(18) . . . . ?
C3 C2 C19 N20 -168.69(12) . . . . ?
N20 C21 C22 C27 82.2(2) . . . . ?
N20 C21 C22 C23 -98.81(18) . . . . ?
C27 C22 C23 C24 -0.7(2) . . . . ?
C21 C22 C23 C24 -179.70(15) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C27 0.6(3) . . . . ?
C25 C26 C27 C22 -1.4(3) . . . . ?
C23 C22 C27 C26 1.5(3) . . . . ?
C21 C22 C27 C26 -179.58(17) . . . . ?
C1 C2 C28 N29 -73.01(17) . . . . ?
C19 C2 C28 N29 50.76(18) . . . . ?
C3 C2 C28 N29 167.59(13) . . . . ?
N29 C30 C31 C36 104.79(18) . . . . ?
N29 C30 C31 C32 -75.81(19) . . . . ?
C36 C31 C32 C33 -1.2(2) . . . . ?
C30 C31 C32 C33 179.35(15) . . . . ?
C31 C32 C33 C34 0.4(3) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
C34 C35 C36 C31 -0.4(3) . . . . ?
C32 C31 C36 C35 1.2(2) . . . . ?
C30 C31 C36 C35 -179.34(16) . . . . ?
N29 C37 C38 C39 57.1(2) . . . . ?
C37 C38 C39 N20 -58.0(2) . . . . ?
C6 C5 N4 C3 170.05(13) . . . . ?
C6 C5 N4 C12 -63.27(18) . . . . ?
C2 C3 N4 C5 -107.89(16) . . . . ?
C2 C3 N4 C12 125.84(15) . . . . ?
C13 C12 N4 C5 156.55(14) . . . . ?
C13 C12 N4 C3 -77.11(18) . . . . ?
C22 C21 N20 C39 -173.51(15) . . . . ?
C22 C21 N20 C19 61.98(19) . . . . ?
C38 C39 N20 C21 177.45(15) . . . . ?
C38 C39 N20 C19 -56.94(19) . . . . ?
C2 C19 N20 C21 -125.87(15) . . . . ?
C2 C19 N20 C39 111.13(15) . . . . ?
C31 C30 N29 C37 163.07(14) . . . . ?
C31 C30 N29 C28 -72.62(17) . . . . ?
C38 C37 N29 C30 -173.19(15) . . . . ?
C38 C37 N29 C28 61.73(19) . . . . ?
C2 C28 N29 C30 125.02(15) . . . . ?
C2 C28 N29 C37 -111.96(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B F6B 0.99 2.43 3.367(9) 159 1_455
C12 H12B F6C 0.99 2.34 3.301(14) 164 1_455
C37 H37B F1 0.99 2.55 3.154(2) 119 .
C38 H38A F3B 0.99 2.55 3.336(5) 136 3_667
C38 H38A F3C 0.99 2.53 3.160(15) 122 3_667
C39 H39A F4A 0.99 2.46 3.275(4) 139 3_667
C39 H39A F3C 0.99 2.48 3.063(15) 117 3_667
N20 H20 N29 0.90(2) 2.01(2) 2.691(2) 131.9(17) .

_refine_diff_density_max         0.609
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_tcd217
_database_code_depnum_ccdc_archive 'CCDC 1415370'
_audit_update_record             
;
2015-07-27 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H45 N3, 2(C F3 O3 S)'
_chemical_formula_sum            'C38 H45 F6 N3 O6 S2'
_chemical_formula_weight         817.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.1337(5)
_cell_length_b                   24.2066(10)
_cell_length_c                   15.0351(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.5700(10)
_cell_angle_gamma                90
_cell_volume                     3863.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      30.53

_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker, 2014)'

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.258
_diffrn_reflns_number            185743
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.651
_diffrn_reflns_theta_max         30.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11856
_reflns_number_gt                9748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker-AXS, 2008-2014)'
_computing_publication_material  'SHELXTL (Bruker-AXS, 2008-2014)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+2.1248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11856
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.62153(11) 0.30949(5) 0.39502(8) 0.0168(2) Uani 1 1 d . . . . .
H1A H 0.5736 0.2843 0.4225 0.025 Uiso 1 1 calc R U . . .
H1B H 0.5702 0.3421 0.3700 0.025 Uiso 1 1 calc R U . . .
H1C H 0.6985 0.3210 0.4430 0.025 Uiso 1 1 calc R U . . .
C2 C 0.65652(10) 0.27983(5) 0.31596(8) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.73925(10) 0.22873(5) 0.35487(8) 0.0155(2) Uani 1 1 d . . . . .
H42A H 0.6936 0.2041 0.3862 0.019 Uiso 1 1 calc R U . . .
H42B H 0.7543 0.2080 0.3025 0.019 Uiso 1 1 calc R U . . .
C5 C 0.96979(11) 0.22976(5) 0.38934(9) 0.0203(2) Uani 1 1 d . . . . .
H5A H 0.9693 0.1895 0.3777 0.024 Uiso 1 1 calc R U . . .
H5B H 1.0489 0.2389 0.4387 0.024 Uiso 1 1 calc R U . . .
C6 C 0.96627(11) 0.26061(5) 0.30032(9) 0.0198(2) Uani 1 1 d . . . . .
H6A H 1.0425 0.2508 0.2829 0.024 Uiso 1 1 calc R U . . .
H6B H 0.8922 0.2478 0.2495 0.024 Uiso 1 1 calc R U . . .
C7 C 0.95978(11) 0.32312(5) 0.30722(9) 0.0187(2) Uani 1 1 d . . . . .
H7A H 1.0349 0.3360 0.3571 0.022 Uiso 1 1 calc R U . . .
H7B H 0.9638 0.3394 0.2478 0.022 Uiso 1 1 calc R U . . .
C9 C 0.72158(10) 0.32055(5) 0.26561(8) 0.0148(2) Uani 1 1 d . . . . .
H9A H 0.7396 0.3010 0.2132 0.018 Uiso 1 1 calc R U . . .
H9B H 0.6623 0.3510 0.2388 0.018 Uiso 1 1 calc R U . . .
C10 C 0.53664(10) 0.26403(5) 0.23612(8) 0.0158(2) Uani 1 1 d . . . . .
H10A H 0.4906 0.2984 0.2112 0.019 Uiso 1 1 calc R U . . .
H10B H 0.5633 0.2471 0.1852 0.019 Uiso 1 1 calc R U . . .
C12 C 0.31240(11) 0.24891(5) 0.23841(9) 0.0204(2) Uani 1 1 d . . . . .
H12A H 0.2787 0.2542 0.1701 0.025 Uiso 1 1 calc R U . . .
H12B H 0.2578 0.2217 0.2567 0.025 Uiso 1 1 calc R U . . .
C13 C 0.30412(10) 0.30302(5) 0.28550(9) 0.0186(2) Uani 1 1 d . . . . .
C14 C 0.30319(11) 0.30497(6) 0.37825(9) 0.0218(2) Uani 1 1 d . . . . .
H14 H 0.3104 0.2718 0.4133 0.026 Uiso 1 1 calc R U . . .
C15 C 0.29167(12) 0.35546(6) 0.41916(10) 0.0248(3) Uani 1 1 d . . . . .
H15 H 0.2924 0.3567 0.4825 0.030 Uiso 1 1 calc R U . . .
C16 C 0.27903(13) 0.40402(6) 0.36787(10) 0.0274(3) Uani 1 1 d . . . . .
H16 H 0.2709 0.4384 0.3960 0.033 Uiso 1 1 calc R U . . .
C17 C 0.27830(13) 0.40228(6) 0.27553(10) 0.0268(3) Uani 1 1 d . . . . .
H17 H 0.2692 0.4354 0.2403 0.032 Uiso 1 1 calc R U . . .
C18 C 0.29086(12) 0.35201(6) 0.23440(9) 0.0225(2) Uani 1 1 d . . . . .
H18 H 0.2904 0.3510 0.1711 0.027 Uiso 1 1 calc R U . . .
C19 C 0.43111(11) 0.16927(5) 0.20999(9) 0.0202(2) Uani 1 1 d . . . . .
H19A H 0.3785 0.1447 0.2355 0.024 Uiso 1 1 calc R U . . .
H19B H 0.3854 0.1755 0.1433 0.024 Uiso 1 1 calc R U . . .
C20 C 0.55287(11) 0.14030(5) 0.21695(9) 0.0186(2) Uani 1 1 d . . . . .
C21 C 0.61377(12) 0.10865(5) 0.29512(9) 0.0199(2) Uani 1 1 d . . . . .
H21 H 0.5761 0.1039 0.3435 0.024 Uiso 1 1 calc R U . . .
C22 C 0.72932(12) 0.08409(5) 0.30256(10) 0.0236(2) Uani 1 1 d . . . . .
H22 H 0.7704 0.0627 0.3561 0.028 Uiso 1 1 calc R U . . .
C23 C 0.78488(13) 0.09072(6) 0.23183(10) 0.0273(3) Uani 1 1 d . . . . .
H23 H 0.8650 0.0748 0.2379 0.033 Uiso 1 1 calc R U . . .
C24 C 0.72312(13) 0.12064(6) 0.15229(10) 0.0270(3) Uani 1 1 d . . . . .
H24 H 0.7601 0.1245 0.1033 0.032 Uiso 1 1 calc R U . . .
C25 C 0.60706(12) 0.14494(6) 0.14443(9) 0.0225(2) Uani 1 1 d . . . . .
H25 H 0.5643 0.1648 0.0895 0.027 Uiso 1 1 calc R U . . .
C26 C 0.87843(12) 0.22546(5) 0.51830(9) 0.0198(2) Uani 1 1 d . . . . .
H26A H 0.8084 0.2406 0.5387 0.024 Uiso 1 1 calc R U . . .
H26B H 0.9575 0.2417 0.5591 0.024 Uiso 1 1 calc R U . . .
C27 C 0.88352(11) 0.16337(5) 0.53423(9) 0.0192(2) Uani 1 1 d . . . . .
C28 C 0.77660(12) 0.13425(5) 0.53739(9) 0.0214(2) Uani 1 1 d . . . . .
H28 H 0.6998 0.1535 0.5296 0.026 Uiso 1 1 calc R U . . .
C29 C 0.78099(13) 0.07740(6) 0.55173(10) 0.0256(3) Uani 1 1 d . . . . .
H29 H 0.7070 0.0581 0.5526 0.031 Uiso 1 1 calc R U . . .
C30 C 0.89284(15) 0.04877(6) 0.56476(10) 0.0285(3) Uani 1 1 d . . . . .
H30 H 0.8960 0.0100 0.5752 0.034 Uiso 1 1 calc R U . . .
C31 C 1.00038(14) 0.07723(6) 0.56246(11) 0.0297(3) Uani 1 1 d . . . . .
H31 H 1.0773 0.0579 0.5713 0.036 Uiso 1 1 calc R U . . .
C32 C 0.99559(12) 0.13405(6) 0.54725(10) 0.0257(3) Uani 1 1 d . . . . .
H32 H 1.0695 0.1531 0.5457 0.031 Uiso 1 1 calc R U . . .
C33 C 0.84668(11) 0.40788(5) 0.32066(9) 0.0172(2) Uani 1 1 d . . . . .
H33A H 0.9230 0.4215 0.3686 0.021 Uiso 1 1 calc R U . . .
H33B H 0.8548 0.4178 0.2589 0.021 Uiso 1 1 calc R U . . .
C34 C 0.73340(11) 0.43734(5) 0.33310(9) 0.0167(2) Uani 1 1 d . . . . .
C35 C 0.63851(12) 0.45521(5) 0.25425(9) 0.0200(2) Uani 1 1 d . . . . .
H35 H 0.6447 0.4475 0.1938 0.024 Uiso 1 1 calc R U . . .
C36 C 0.53522(12) 0.48421(5) 0.26352(10) 0.0225(2) Uani 1 1 d . . . . .
H36 H 0.4711 0.4962 0.2095 0.027 Uiso 1 1 calc R U . . .
C37 C 0.52568(12) 0.49568(5) 0.35152(10) 0.0227(2) Uani 1 1 d . . . . .
H37 H 0.4554 0.5157 0.3579 0.027 Uiso 1 1 calc R U . . .
C38 C 0.61921(12) 0.47781(5) 0.43026(9) 0.0218(2) Uani 1 1 d . . . . .
H38 H 0.6121 0.4853 0.4905 0.026 Uiso 1 1 calc R U . . .
C39 C 0.72336(12) 0.44900(5) 0.42140(9) 0.0189(2) Uani 1 1 d . . . . .
H39 H 0.7876 0.4373 0.4755 0.023 Uiso 1 1 calc R U . . .
C40 C 0.10563(12) 0.42527(5) 0.60512(9) 0.0211(2) Uani 1 1 d . . . . .
C41 C 0.32518(18) 0.09597(9) 0.44802(13) 0.0457(5) Uani 1 1 d . . . . .
N4 N 0.86158(9) 0.24418(4) 0.42190(7) 0.01638(18) Uani 1 1 d . . . . .
N8 N 0.84285(9) 0.34506(4) 0.32748(7) 0.01432(18) Uani 1 1 d . . . . .
H8 H 0.8517(16) 0.3372(7) 0.3865(12) 0.023(4) Uiso 1 1 d . . . . .
N11 N 0.44570(9) 0.22481(4) 0.26121(7) 0.01590(18) Uani 1 1 d . . . . .
H11 H 0.4703(15) 0.2167(7) 0.3240(12) 0.023(4) Uiso 1 1 d . . . . .
S1 S 0.04769(3) 0.35422(2) 0.59509(2) 0.01533(6) Uani 1 1 d . . . . .
S2 S 0.41116(3) 0.15691(2) 0.50297(2) 0.01895(7) Uani 1 1 d . . . . .
F1 F 0.22200(8) 0.42874(3) 0.66402(7) 0.0332(2) Uani 1 1 d . . . . .
F2 F 0.10826(9) 0.44423(4) 0.52193(6) 0.0333(2) Uani 1 1 d . . . . .
F3 F 0.03220(9) 0.45920(3) 0.63570(7) 0.0359(2) Uani 1 1 d . . . . .
F4 F 0.27262(13) 0.07082(6) 0.50583(10) 0.0692(4) Uani 1 1 d . . . . .
F5 F 0.40166(15) 0.05975(5) 0.42612(11) 0.0718(4) Uani 1 1 d . . . . .
F6 F 0.23493(14) 0.10929(9) 0.37056(10) 0.0953(6) Uani 1 1 d . . . . .
O1 O -0.07534(8) 0.35957(4) 0.52606(6) 0.01902(17) Uani 1 1 d . . . . .
O2 O 0.13854(8) 0.32447(4) 0.56270(7) 0.02331(19) Uani 1 1 d . . . . .
O3 O 0.04568(10) 0.34077(4) 0.68760(7) 0.0262(2) Uani 1 1 d . . . . .
O4 O 0.50250(9) 0.13546(4) 0.58424(7) 0.0273(2) Uani 1 1 d . . . . .
O5 O 0.46483(10) 0.17755(4) 0.43251(7) 0.0292(2) Uani 1 1 d . . . . .
O6 O 0.31593(11) 0.19171(5) 0.52042(8) 0.0350(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5361(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5476(16) . ?
C2 C9 1.5494(15) . ?
C2 C10 1.5496(16) . ?
C3 N4 1.4770(14) . ?
C3 H42A 0.9900 . ?
C3 H42B 0.9900 . ?
C5 N4 1.4728(15) . ?
C5 C6 1.5227(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5199(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N8 1.5196(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 N8 1.5106(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N11 1.5165(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C13 1.5049(17) . ?
C12 N11 1.5340(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.3965(18) . ?
C13 C14 1.3984(18) . ?
C14 C15 1.3914(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3910(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.5016(17) . ?
C19 N11 1.5333(15) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.3955(18) . ?
C20 C25 1.4009(17) . ?
C21 C22 1.3906(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.3917(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3920(19) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 N4 1.4755(16) . ?
C26 C27 1.5205(17) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.3965(17) . ?
C27 C32 1.3968(18) . ?
C28 C29 1.3917(19) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.391(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.3927(19) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.5088(16) . ?
C33 N8 1.5258(15) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C39 1.3942(17) . ?
C34 C35 1.3974(17) . ?
C35 C36 1.3896(17) . ?
C35 H35 0.9500 . ?
C36 C37 1.3871(19) . ?
C36 H36 0.9500 . ?
C37 C38 1.3888(19) . ?
C37 H37 0.9500 . ?
C38 C39 1.3936(17) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 F1 1.3332(14) . ?
C40 F3 1.3347(15) . ?
C40 F2 1.3410(16) . ?
C40 S1 1.8271(12) . ?
C41 F6 1.328(3) . ?
C41 F5 1.331(2) . ?
C41 F4 1.332(2) . ?
C41 S2 1.8160(17) . ?
N8 H8 0.883(17) . ?
N11 H11 0.921(17) . ?
S1 O3 1.4352(10) . ?
S1 O2 1.4409(9) . ?
S1 O1 1.4532(9) . ?
S2 O4 1.4306(10) . ?
S2 O6 1.4390(10) . ?
S2 O5 1.4530(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 110.00(9) . . ?
C1 C2 C9 110.24(9) . . ?
C3 C2 C9 112.36(9) . . ?
C1 C2 C10 110.76(9) . . ?
C3 C2 C10 111.77(9) . . ?
C9 C2 C10 101.47(9) . . ?
N4 C3 C2 112.12(9) . . ?
N4 C3 H42A 109.2 . . ?
C2 C3 H42A 109.2 . . ?
N4 C3 H42B 109.2 . . ?
C2 C3 H42B 109.2 . . ?
H42A C3 H42B 107.9 . . ?
N4 C5 C6 111.68(10) . . ?
N4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 114.66(10) . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
N8 C7 C6 115.01(9) . . ?
N8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
N8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N8 C9 C2 114.31(9) . . ?
N8 C9 H9A 108.7 . . ?
C2 C9 H9A 108.7 . . ?
N8 C9 H9B 108.7 . . ?
C2 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N11 C10 C2 116.45(9) . . ?
N11 C10 H10A 108.2 . . ?
C2 C10 H10A 108.2 . . ?
N11 C10 H10B 108.2 . . ?
C2 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C13 C12 N11 114.73(9) . . ?
C13 C12 H12A 108.6 . . ?
N11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
N11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C18 C13 C14 119.24(12) . . ?
C18 C13 C12 119.45(11) . . ?
C14 C13 C12 121.24(12) . . ?
C15 C14 C13 120.00(12) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.33(12) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.95(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.03(13) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.44(12) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C20 C19 N11 114.71(9) . . ?
C20 C19 H19A 108.6 . . ?
N11 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
N11 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C21 C20 C25 119.05(12) . . ?
C21 C20 C19 120.93(11) . . ?
C25 C20 C19 120.02(12) . . ?
C22 C21 C20 120.33(12) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.20(13) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 119.94(13) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 119.92(12) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.46(13) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
N4 C26 C27 116.49(10) . . ?
N4 C26 H26A 108.2 . . ?
C27 C26 H26A 108.2 . . ?
N4 C26 H26B 108.2 . . ?
C27 C26 H26B 108.2 . . ?
H26A C26 H26B 107.3 . . ?
C28 C27 C32 118.25(12) . . ?
C28 C27 C26 120.84(11) . . ?
C32 C27 C26 120.90(11) . . ?
C29 C28 C27 120.92(12) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C28 120.29(12) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 119.48(13) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C30 C31 C32 120.18(13) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C27 120.87(12) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?
C34 C33 N8 114.92(9) . . ?
C34 C33 H33A 108.5 . . ?
N8 C33 H33A 108.5 . . ?
C34 C33 H33B 108.5 . . ?
N8 C33 H33B 108.5 . . ?
H33A C33 H33B 107.5 . . ?
C39 C34 C35 119.19(11) . . ?
C39 C34 C33 121.60(11) . . ?
C35 C34 C33 119.16(11) . . ?
C36 C35 C34 120.53(12) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C37 C36 C35 120.05(12) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 119.81(12) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C37 C38 C39 120.38(12) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C38 C39 C34 120.03(12) . . ?
C38 C39 H39 120.0 . . ?
C34 C39 H39 120.0 . . ?
F1 C40 F3 107.81(11) . . ?
F1 C40 F2 107.91(11) . . ?
F3 C40 F2 107.38(10) . . ?
F1 C40 S1 111.25(8) . . ?
F3 C40 S1 111.72(9) . . ?
F2 C40 S1 110.60(9) . . ?
F6 C41 F5 108.32(16) . . ?
F6 C41 F4 108.55(16) . . ?
F5 C41 F4 107.47(18) . . ?
F6 C41 S2 110.92(16) . . ?
F5 C41 S2 111.03(12) . . ?
F4 C41 S2 110.44(12) . . ?
C5 N4 C26 112.30(10) . . ?
C5 N4 C3 113.05(9) . . ?
C26 N4 C3 114.21(9) . . ?
C9 N8 C7 113.57(9) . . ?
C9 N8 C33 112.83(9) . . ?
C7 N8 C33 106.97(8) . . ?
C9 N8 H8 110.0(11) . . ?
C7 N8 H8 106.4(11) . . ?
C33 N8 H8 106.7(11) . . ?
C10 N11 C19 113.67(9) . . ?
C10 N11 C12 112.33(9) . . ?
C19 N11 C12 105.81(9) . . ?
C10 N11 H11 111.9(10) . . ?
C19 N11 H11 106.4(10) . . ?
C12 N11 H11 106.2(10) . . ?
O3 S1 O2 115.60(6) . . ?
O3 S1 O1 115.17(6) . . ?
O2 S1 O1 114.18(6) . . ?
O3 S1 C40 104.00(6) . . ?
O2 S1 C40 103.41(6) . . ?
O1 S1 C40 102.02(5) . . ?
O4 S2 O6 115.45(6) . . ?
O4 S2 O5 113.88(6) . . ?
O6 S2 O5 114.80(6) . . ?
O4 S2 C41 103.59(9) . . ?
O6 S2 C41 104.02(8) . . ?
O5 S2 C41 102.94(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
C1 C2 C3 N4 -64.26(12) . . . . ?
C9 C2 C3 N4 58.96(12) . . . . ?
C10 C2 C3 N4 172.27(9) . . . . ?
N4 C5 C6 C7 55.92(13) . . . . ?
C5 C6 C7 N8 -62.13(14) . . . . ?
C1 C2 C9 N8 61.03(12) . . . . ?
C3 C2 C9 N8 -62.06(12) . . . . ?
C10 C2 C9 N8 178.43(9) . . . . ?
C1 C2 C10 N11 -61.30(13) . . . . ?
C3 C2 C10 N11 61.74(12) . . . . ?
C9 C2 C10 N11 -178.32(9) . . . . ?
N11 C12 C13 C18 102.76(13) . . . . ?
N11 C12 C13 C14 -80.44(14) . . . . ?
C18 C13 C14 C15 -1.27(17) . . . . ?
C12 C13 C14 C15 -178.08(11) . . . . ?
C13 C14 C15 C16 1.02(18) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C13 0.1(2) . . . . ?
C14 C13 C18 C17 0.73(18) . . . . ?
C12 C13 C18 C17 177.59(11) . . . . ?
N11 C19 C20 C21 82.08(14) . . . . ?
N11 C19 C20 C25 -97.76(13) . . . . ?
C25 C20 C21 C22 2.77(18) . . . . ?
C19 C20 C21 C22 -177.08(11) . . . . ?
C20 C21 C22 C23 -0.26(19) . . . . ?
C21 C22 C23 C24 -1.9(2) . . . . ?
C22 C23 C24 C25 1.4(2) . . . . ?
C23 C24 C25 C20 1.1(2) . . . . ?
C21 C20 C25 C24 -3.21(18) . . . . ?
C19 C20 C25 C24 176.64(12) . . . . ?
N4 C26 C27 C28 -97.69(14) . . . . ?
N4 C26 C27 C32 83.12(15) . . . . ?
C32 C27 C28 C29 -0.95(19) . . . . ?
C26 C27 C28 C29 179.83(12) . . . . ?
C27 C28 C29 C30 1.1(2) . . . . ?
C28 C29 C30 C31 -0.6(2) . . . . ?
C29 C30 C31 C32 0.0(2) . . . . ?
C30 C31 C32 C27 0.1(2) . . . . ?
C28 C27 C32 C31 0.4(2) . . . . ?
C26 C27 C32 C31 179.57(13) . . . . ?
N8 C33 C34 C39 82.94(14) . . . . ?
N8 C33 C34 C35 -99.53(13) . . . . ?
C39 C34 C35 C36 -0.08(18) . . . . ?
C33 C34 C35 C36 -177.67(11) . . . . ?
C34 C35 C36 C37 0.05(19) . . . . ?
C35 C36 C37 C38 -0.40(19) . . . . ?
C36 C37 C38 C39 0.78(19) . . . . ?
C37 C38 C39 C34 -0.81(18) . . . . ?
C35 C34 C39 C38 0.45(17) . . . . ?
C33 C34 C39 C38 177.98(11) . . . . ?
C6 C5 N4 C26 -166.42(10) . . . . ?
C6 C5 N4 C3 62.57(13) . . . . ?
C27 C26 N4 C5 -65.26(13) . . . . ?
C27 C26 N4 C3 65.16(13) . . . . ?
C2 C3 N4 C5 -115.69(11) . . . . ?
C2 C3 N4 C26 114.25(11) . . . . ?
C2 C9 N8 C7 108.58(11) . . . . ?
C2 C9 N8 C33 -129.48(10) . . . . ?
C6 C7 N8 C9 -48.53(14) . . . . ?
C6 C7 N8 C33 -173.67(10) . . . . ?
C34 C33 N8 C9 50.95(13) . . . . ?
C34 C33 N8 C7 176.54(10) . . . . ?
C2 C10 N11 C19 -116.23(11) . . . . ?
C2 C10 N11 C12 123.65(11) . . . . ?
C20 C19 N11 C10 51.80(14) . . . . ?
C20 C19 N11 C12 175.53(10) . . . . ?
C13 C12 N11 C10 -57.90(14) . . . . ?
C13 C12 N11 C19 177.53(10) . . . . ?
F1 C40 S1 O3 62.27(11) . . . . ?
F3 C40 S1 O3 -58.27(10) . . . . ?
F2 C40 S1 O3 -177.82(9) . . . . ?
F1 C40 S1 O2 -58.87(11) . . . . ?
F3 C40 S1 O2 -179.42(9) . . . . ?
F2 C40 S1 O2 61.03(10) . . . . ?
F1 C40 S1 O1 -177.65(9) . . . . ?
F3 C40 S1 O1 61.81(10) . . . . ?
F2 C40 S1 O1 -57.74(10) . . . . ?
F6 C41 S2 O4 179.61(13) . . . . ?
F5 C41 S2 O4 -59.90(15) . . . . ?
F4 C41 S2 O4 59.22(16) . . . . ?
F6 C41 S2 O6 58.54(14) . . . . ?
F5 C41 S2 O6 179.03(14) . . . . ?
F4 C41 S2 O6 -61.85(17) . . . . ?
F6 C41 S2 O5 -61.52(14) . . . . ?
F5 C41 S2 O5 58.97(16) . . . . ?
F4 C41 S2 O5 178.09(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9B O4 0.99 2.49 3.2410(15) 133 4_565
C10 H10A O4 0.99 2.53 3.2794(16) 133 4_565
C19 H19A F1 0.99 2.49 3.2490(15) 133 4_565
N8 H8 N4 0.883(17) 2.308(17) 2.8003(14) 115.2(13) .
N8 H8 O1 0.883(17) 2.081(17) 2.8679(14) 148.0(15) 1_655
N11 H11 O5 0.921(17) 1.904(17) 2.7671(14) 155.1(15) .

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_tcd209
_database_code_depnum_ccdc_archive 'CCDC 1415371'
_audit_update_record             
;
2015-07-27 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H29 Br0.68 Cl0.32 N2 O4 S2'
_chemical_formula_sum            'C22 H29 Br0.68 Cl0.32 N2 O4 S2'
_chemical_formula_weight         515.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.9261(5)
_cell_length_b                   12.7024(5)
_cell_length_c                   17.0382(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.0531(13)
_cell_angle_gamma                90
_cell_volume                     2351.51(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      68.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             1073
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.996
_shelx_estimated_absorpt_T_min   0.473
_shelx_estimated_absorpt_T_max   0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker, 2014)'

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus source'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8.258
_diffrn_reflns_number            31099
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.069
_diffrn_reflns_theta_max         68.370
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4316
_reflns_number_gt                4110
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker-AXS, 2008-2014)'
_computing_publication_material  'SHELXTL (Bruker-AXS, 2008-2014)'

_refine_special_details          
;
Halide positions were modelled as half occupied with contraints (EADP)
and restraints (DFIX) used to allow the model to converge. Each halide 
position was modelled as split between Br and Cl with refined occupancies
of 0.35/0.15 Br1a/Cl1a and 0.33/0.17 Br1b/Cl1b.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+5.1258P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4316
_refine_ls_number_parameters     303
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.7989(3) 0.4824(3) 0.8214(2) 0.0418(8) Uani 1 1 d . . . . .
H1A H 0.8627 0.4285 0.8195 0.063 Uiso 1 1 calc R U . . .
H1B H 0.7834 0.4942 0.8763 0.063 Uiso 1 1 calc R U . . .
H1C H 0.8266 0.5483 0.7990 0.063 Uiso 1 1 calc R U . . .
C2 C 0.6821(3) 0.4460(3) 0.77423(17) 0.0322(7) Uani 1 1 d . . . . .
C3 C 0.5751(3) 0.5062(2) 0.77281(18) 0.0325(7) Uani 1 1 d . . . . .
H3 H 0.5768 0.5705 0.8014 0.039 Uiso 1 1 calc R U . . .
C4 C 0.4664(3) 0.4738(2) 0.73052(17) 0.0288(6) Uani 1 1 d . . . . .
H4 H 0.3942 0.5156 0.7298 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4641(3) 0.3793(2) 0.68897(16) 0.0251(6) Uani 1 1 d . . . . .
C6 C 0.5700(3) 0.3179(2) 0.68933(17) 0.0293(6) Uani 1 1 d . . . . .
H6 H 0.5683 0.2536 0.6608 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6777(3) 0.3522(3) 0.73192(17) 0.0327(7) Uani 1 1 d . . . . .
H7 H 0.7501 0.3107 0.7322 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2782(3) 0.4939(2) 0.53971(17) 0.0297(6) Uani 1 1 d . . . . .
H9A H 0.3463 0.5384 0.5640 0.036 Uiso 1 1 calc R U . . .
H9B H 0.2060 0.5059 0.5691 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2460(3) 0.5280(2) 0.45435(17) 0.0318(7) Uani 1 1 d . . . . .
H10A H 0.2297 0.6047 0.4535 0.038 Uiso 1 1 calc R U . . .
H10B H 0.3185 0.5157 0.4253 0.038 Uiso 1 1 calc R U . . .
C11 C 0.1357(3) 0.4725(2) 0.41069(18) 0.0324(7) Uani 1 1 d . . . . .
H11A H 0.0618 0.4878 0.4377 0.039 Uiso 1 1 calc R U . . .
H11B H 0.1215 0.5011 0.3564 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2626(3) 0.3217(2) 0.37041(17) 0.0300(6) Uani 1 1 d . . . . .
H13A H 0.2964 0.3825 0.3434 0.036 Uiso 1 1 calc R U . . .
H13B H 0.2370 0.2683 0.3297 0.036 Uiso 1 1 calc R U . . .
C14 C 0.3661(3) 0.2746(2) 0.42832(17) 0.0307(6) Uani 1 1 d . . . . .
C15 C 0.4103(3) 0.3460(2) 0.49877(16) 0.0282(6) Uani 1 1 d . . . . .
H15A H 0.4740 0.3076 0.5332 0.034 Uiso 1 1 calc R U . . .
H15B H 0.4502 0.4088 0.4783 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3272(3) 0.1665(2) 0.45718(19) 0.0361(7) Uani 1 1 d D . . . .
H16D H 0.2841 0.1277 0.4120 0.043 Uiso 0.5 1 calc R U P A 2
H16E H 0.2679 0.1769 0.4966 0.043 Uiso 0.5 1 calc R U P A 2
H16A H 0.3076 0.1198 0.4118 0.054 Uiso 0.5 1 calc R U P B 1
H16B H 0.2544 0.1745 0.4857 0.054 Uiso 0.5 1 calc R U P B 1
H16C H 0.3946 0.1360 0.4925 0.054 Uiso 0.5 1 calc R U P B 1
C17 C 0.4754(3) 0.2626(3) 0.37864(18) 0.0388(8) Uani 1 1 d D . . . .
H17C H 0.4529 0.2140 0.3348 0.058 Uiso 0.5 1 calc R U P C 2
H17D H 0.5468 0.2346 0.4119 0.058 Uiso 0.5 1 calc R U P C 2
H17E H 0.4962 0.3314 0.3577 0.058 Uiso 0.5 1 calc R U P C 2
H17A H 0.4931 0.3319 0.3559 0.047 Uiso 0.5 1 calc R U P D 1
H17B H 0.4512 0.2140 0.3342 0.047 Uiso 0.5 1 calc R U P D 1
C18 C -0.0288(3) 0.3189(2) 0.28569(17) 0.0283(6) Uani 1 1 d . . . . .
C19 C 0.0060(3) 0.2554(3) 0.22516(18) 0.0306(6) Uani 1 1 d . . . . .
H19 H 0.0537 0.1938 0.2369 0.037 Uiso 1 1 calc R U . . .
C20 C -0.0301(3) 0.2835(3) 0.14755(18) 0.0345(7) Uani 1 1 d . . . . .
H20 H -0.0069 0.2405 0.1060 0.041 Uiso 1 1 calc R U . . .
C21 C -0.1000(3) 0.3738(3) 0.12943(19) 0.0382(7) Uani 1 1 d . . . . .
C22 C -0.1346(3) 0.4354(3) 0.19087(19) 0.0382(7) Uani 1 1 d . . . . .
H22 H -0.1827 0.4969 0.1793 0.046 Uiso 1 1 calc R U . . .
C23 C -0.0997(3) 0.4081(3) 0.26896(18) 0.0332(7) Uani 1 1 d . . . . .
H23 H -0.1241 0.4504 0.3106 0.040 Uiso 1 1 calc R U . . .
C24 C -0.1359(4) 0.4072(4) 0.0451(2) 0.0555(11) Uani 1 1 d . . . . .
H24A H -0.2258 0.4079 0.0345 0.083 Uiso 1 1 calc R U . . .
H24B H -0.1015 0.3575 0.0093 0.083 Uiso 1 1 calc R U . . .
H24C H -0.1037 0.4779 0.0368 0.083 Uiso 1 1 calc R U . . .
N8 N 0.3150(2) 0.38214(19) 0.54776(13) 0.0251(5) Uani 1 1 d . . . . .
N12 N 0.1520(2) 0.3571(2) 0.40646(14) 0.0283(5) Uani 1 1 d . . . . .
O1 O 0.22604(18) 0.38270(17) 0.67495(12) 0.0300(5) Uani 1 1 d . . . . .
O2 O 0.3324(2) 0.22318(16) 0.63233(12) 0.0334(5) Uani 1 1 d . . . . .
O3 O -0.06256(19) 0.33053(18) 0.43428(12) 0.0350(5) Uani 1 1 d . . . . .
O4 O 0.0575(2) 0.18068(16) 0.38873(13) 0.0340(5) Uani 1 1 d . . . . .
S1 S 0.32440(6) 0.33534(5) 0.63785(4) 0.02522(17) Uani 1 1 d . . . . .
S2 S 0.02478(7) 0.28959(6) 0.38477(4) 0.02877(18) Uani 1 1 d . . . . .
Br1A Br 0.62261(13) 0.21056(13) 0.43640(10) 0.0328(3) Uani 0.353(3) 1 d D . P E
1
Cl1A Cl 0.6229(6) 0.2311(7) 0.4271(5) 0.0286(14) Uani 0.147(3) 1 d D . P E 3
Br1B Br 0.46439(15) 0.07945(17) 0.50472(9) 0.0328(3) Uani 0.329(3) 1 d D . P F
2
Cl1B Cl 0.4394(6) 0.0879(5) 0.5108(4) 0.0286(14) Uani 0.172(3) 1 d D . P F 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.508(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.391(5) . ?
C2 C3 1.395(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(4) . ?
C5 S1 1.766(3) . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 N8 1.478(4) . ?
C9 C10 1.523(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.479(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 N12 1.482(4) . ?
C13 C14 1.542(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.534(4) . ?
C14 C15 1.542(4) . ?
C14 C17 1.542(4) . ?
C15 N8 1.475(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 Cl1B 1.759(5) . ?
C16 Br1B 1.967(3) . ?
C16 H16D 0.9900 . ?
C16 H16E 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 Cl1A 1.777(5) . ?
C17 Br1A 1.912(3) . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C23 1.386(4) . ?
C18 C19 1.393(4) . ?
C18 S2 1.767(3) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(4) . ?
C21 C24 1.510(5) . ?
C22 C23 1.389(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N8 S1 1.639(2) . ?
N12 S2 1.642(2) . ?
O1 S1 1.435(2) . ?
O2 S1 1.431(2) . ?
O3 S2 1.436(2) . ?
O4 S2 1.429(2) . ?
Br1B Br1B 2.175(4) 3_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.5(3) . . ?
C7 C2 C1 121.3(3) . . ?
C3 C2 C1 120.1(3) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 S1 119.4(2) . . ?
C6 C5 S1 119.9(2) . . ?
C7 C6 C5 119.0(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
N8 C9 C10 113.3(2) . . ?
N8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 115.2(3) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N12 C11 C10 112.9(3) . . ?
N12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
N12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N12 C13 C14 115.3(2) . . ?
N12 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
N12 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C16 C14 C15 110.6(2) . . ?
C16 C14 C13 110.1(2) . . ?
C15 C14 C13 114.7(3) . . ?
C16 C14 C17 110.1(3) . . ?
C15 C14 C17 106.8(2) . . ?
C13 C14 C17 104.2(2) . . ?
N8 C15 C14 116.2(2) . . ?
N8 C15 H15A 108.2 . . ?
C14 C15 H15A 108.2 . . ?
N8 C15 H15B 108.2 . . ?
C14 C15 H15B 108.2 . . ?
H15A C15 H15B 107.4 . . ?
C14 C16 Cl1B 118.2(3) . . ?
C14 C16 Br1B 114.2(2) . . ?
C14 C16 H16D 108.7 . . ?
Br1B C16 H16D 108.7 . . ?
C14 C16 H16E 108.7 . . ?
Br1B C16 H16E 108.7 . . ?
H16D C16 H16E 107.6 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 Cl1A 119.0(4) . . ?
C14 C17 Br1A 114.2(2) . . ?
C14 C17 H17C 109.5 . . ?
C14 C17 H17D 109.5 . . ?
H17C C17 H17D 109.5 . . ?
C14 C17 H17E 109.5 . . ?
H17C C17 H17E 109.5 . . ?
H17D C17 H17E 109.5 . . ?
C14 C17 H17A 108.7 . . ?
Br1A C17 H17A 108.7 . . ?
C14 C17 H17B 108.7 . . ?
Br1A C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C23 C18 C19 120.8(3) . . ?
C23 C18 S2 119.4(2) . . ?
C19 C18 S2 119.8(2) . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 C24 119.6(3) . . ?
C20 C21 C24 121.5(3) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C18 C23 C22 119.5(3) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 N8 C9 116.6(2) . . ?
C15 N8 S1 116.03(19) . . ?
C9 N8 S1 115.14(18) . . ?
C11 N12 C13 115.4(2) . . ?
C11 N12 S2 115.2(2) . . ?
C13 N12 S2 117.1(2) . . ?
O2 S1 O1 120.02(13) . . ?
O2 S1 N8 107.32(12) . . ?
O1 S1 N8 106.53(12) . . ?
O2 S1 C5 106.92(14) . . ?
O1 S1 C5 107.38(13) . . ?
N8 S1 C5 108.23(12) . . ?
O4 S2 O3 120.10(13) . . ?
O4 S2 N12 107.06(13) . . ?
O3 S2 N12 106.12(13) . . ?
O4 S2 C18 107.76(14) . . ?
O3 S2 C18 108.13(13) . . ?
N12 S2 C18 107.00(13) . . ?
C16 Br1B Br1B 138.94(16) . 3_656 ?

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 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C4 -179.4(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 S1 177.7(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
S1 C5 C6 C7 -177.9(2) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C3 C2 C7 C6 -0.3(5) . . . . ?
C1 C2 C7 C6 179.2(3) . . . . ?
N8 C9 C10 C11 63.2(4) . . . . ?
C9 C10 C11 N12 -59.9(4) . . . . ?
N12 C13 C14 C16 71.2(3) . . . . ?
N12 C13 C14 C15 -54.4(3) . . . . ?
N12 C13 C14 C17 -170.7(3) . . . . ?
C16 C14 C15 N8 -69.4(3) . . . . ?
C13 C14 C15 N8 55.8(3) . . . . ?
C17 C14 C15 N8 170.7(2) . . . . ?
C15 C14 C16 Cl1B -62.5(4) . . . . ?
C13 C14 C16 Cl1B 169.6(3) . . . . ?
C17 C14 C16 Cl1B 55.3(4) . . . . ?
C15 C14 C16 Br1B -69.7(3) . . . . ?
C13 C14 C16 Br1B 162.5(2) . . . . ?
C17 C14 C16 Br1B 48.1(3) . . . . ?
C16 C14 C17 Cl1A -72.4(4) . . . . ?
C15 C14 C17 Cl1A 47.8(5) . . . . ?
C13 C14 C17 Cl1A 169.5(4) . . . . ?
C16 C14 C17 Br1A -64.5(3) . . . . ?
C15 C14 C17 Br1A 55.7(3) . . . . ?
C13 C14 C17 Br1A 177.4(2) . . . . ?
C23 C18 C19 C20 0.8(4) . . . . ?
S2 C18 C19 C20 -175.7(2) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C22 -0.7(5) . . . . ?
C19 C20 C21 C24 177.8(3) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C24 C21 C22 C23 -178.1(3) . . . . ?
C19 C18 C23 C22 -1.1(5) . . . . ?
S2 C18 C23 C22 175.5(3) . . . . ?
C21 C22 C23 C18 0.4(5) . . . . ?
C14 C15 N8 C9 -107.1(3) . . . . ?
C14 C15 N8 S1 112.2(2) . . . . ?
C10 C9 N8 C15 50.4(3) . . . . ?
C10 C9 N8 S1 -168.6(2) . . . . ?
C10 C11 N12 C13 -56.2(3) . . . . ?
C10 C11 N12 S2 162.4(2) . . . . ?
C14 C13 N12 C11 108.2(3) . . . . ?
C14 C13 N12 S2 -111.3(3) . . . . ?
C15 N8 S1 O2 -51.9(2) . . . . ?
C9 N8 S1 O2 166.9(2) . . . . ?
C15 N8 S1 O1 178.36(19) . . . . ?
C9 N8 S1 O1 37.1(2) . . . . ?
C15 N8 S1 C5 63.2(2) . . . . ?
C9 N8 S1 C5 -78.0(2) . . . . ?
C4 C5 S1 O2 -154.3(2) . . . . ?
C6 C5 S1 O2 23.9(3) . . . . ?
C4 C5 S1 O1 -24.3(3) . . . . ?
C6 C5 S1 O1 153.9(2) . . . . ?
C4 C5 S1 N8 90.4(2) . . . . ?
C6 C5 S1 N8 -91.4(2) . . . . ?
C11 N12 S2 O4 -176.1(2) . . . . ?
C13 N12 S2 O4 43.3(2) . . . . ?
C11 N12 S2 O3 -46.7(2) . . . . ?
C13 N12 S2 O3 172.7(2) . . . . ?
C11 N12 S2 C18 68.6(2) . . . . ?
C13 N12 S2 C18 -72.0(2) . . . . ?
C23 C18 S2 O4 160.9(2) . . . . ?
C19 C18 S2 O4 -22.5(3) . . . . ?
C23 C18 S2 O3 29.7(3) . . . . ?
C19 C18 S2 O3 -153.8(2) . . . . ?
C23 C18 S2 N12 -84.3(3) . . . . ?
C19 C18 S2 N12 92.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9B O3 0.99 2.60 3.307(4) 129 3_566
C16 H16D O4 0.99 2.56 3.058(4) 111 .
C16 H16E O2 0.99 2.42 3.065(4) 122 .
C17 H17D Br1B 0.98 2.74 3.177(4) 108 .
C19 H19 O1 0.95 2.45 3.166(4) 132 4_565
C23 H23 O1 0.95 2.42 3.187(4) 138 3_566

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.066

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

data_tcd32_a
_database_code_depnum_ccdc_archive 'CCDC 1415372'
_audit_update_record             
;
2015-07-27 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Br12 N6'
_chemical_formula_weight         1351.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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                   19.6192(13)
_cell_length_b                   19.6192(13)
_cell_length_c                   22.6973(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7566.0(11)
_cell_formula_units_Z            9
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.669
_exptl_crystal_F_000             5634
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    14.323
_shelx_estimated_absorpt_T_min   0.223
_shelx_estimated_absorpt_T_max   0.328
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26536
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.497
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4199
_reflns_number_gt                3528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+166.1049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4199
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Br01 Br 0.6667 0.3333 0.8333 0.0147(2) Uani 1 6 d S T P . .
Br02 Br 0.6667 0.3333 0.65159(4) 0.01714(18) Uani 1 3 d S T P . .
Br03 Br 0.17764(3) 0.20636(3) 0.54983(2) 0.01930(14) Uani 1 1 d . . . . .
Br04 Br 0.25331(4) 0.40852(5) 0.70308(3) 0.03787(19) Uani 1 1 d . . . . .
Br05 Br 0.46551(4) 0.18017(4) 0.56394(3) 0.0406(2) Uani 1 1 d . . . . .
N006 N 0.5261(3) 0.3051(3) 0.74901(19) 0.0208(9) Uani 1 1 d . . . . .
H00P H 0.5314 0.2648 0.7636 0.031 Uiso 1 1 calc R U . . .
H00R H 0.5698 0.3382 0.7281 0.031 Uiso 1 1 calc R U . . .
H00S H 0.5199 0.3319 0.7793 0.031 Uiso 1 1 calc R U . . .
N007 N 0.5297(3) 0.3707(3) 0.5904(2) 0.0243(9) Uani 1 1 d . . . . .
H00A H 0.5050 0.3172 0.5909 0.029 Uiso 1 1 calc R U . . .
H00B H 0.5823 0.3891 0.5880 0.029 Uiso 1 1 calc R U . . .
N008 N 0.3309(3) 0.3305(3) 0.6178(2) 0.0240(9) Uani 1 1 d . . . . .
H00C H 0.3226 0.3578 0.6466 0.029 Uiso 1 1 calc R U . . .
H00D H 0.2827 0.2938 0.6040 0.029 Uiso 1 1 calc R U . . .
C009 C 0.5133(3) 0.3980(3) 0.6475(2) 0.0195(10) Uani 1 1 d . . . . .
H00E H 0.5058 0.4434 0.6392 0.023 Uiso 1 1 calc R U . . .
H00F H 0.5604 0.4172 0.6728 0.023 Uiso 1 1 calc R U . . .
C00A C 0.4560(3) 0.2731(3) 0.7099(2) 0.0198(10) Uani 1 1 d . . . . .
H00G H 0.4089 0.2361 0.7329 0.024 Uiso 1 1 calc R U . . .
H00H H 0.4627 0.2429 0.6777 0.024 Uiso 1 1 calc R U . . .
C00B C 0.4414(3) 0.3367(3) 0.6828(2) 0.0169(9) Uani 1 1 d . . . . .
C00C C 0.3671(3) 0.2876(3) 0.6458(2) 0.0208(10) Uani 1 1 d . . . . .
H00I H 0.3802 0.2611 0.6144 0.025 Uiso 1 1 calc R U . . .
H00J H 0.3271 0.2460 0.6714 0.025 Uiso 1 1 calc R U . . .
C00D C 0.4244(3) 0.3804(3) 0.7319(2) 0.0236(11) Uani 1 1 d . . . . .
C00E C 0.3734(3) 0.3870(3) 0.5682(3) 0.0288(12) Uani 1 1 d . . . . .
H00K H 0.4123 0.4385 0.5852 0.035 Uiso 1 1 calc R U . . .
H00L H 0.3350 0.3949 0.5454 0.035 Uiso 1 1 calc R U . . .
C00F C 0.4156(4) 0.3600(4) 0.5267(3) 0.0327(14) Uani 1 1 d . . . . .
H00M H 0.4067 0.3718 0.4859 0.039 Uiso 1 1 calc R U . . .
H00N H 0.3908 0.3022 0.5301 0.039 Uiso 1 1 calc R U . . .
C00G C 0.5041(4) 0.3959(4) 0.5358(3) 0.0340(14) Uani 1 1 d . . . . .
H00O H 0.5259 0.3828 0.5011 0.041 Uiso 1 1 calc R U . . .
H00Q H 0.5281 0.4539 0.5368 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N006 C00A 1.486(6) . ?
N006 H00P 0.9100 . ?
N006 H00R 0.9100 . ?
N006 H00S 0.9100 . ?
N007 C009 1.496(7) . ?
N007 C00G 1.511(7) . ?
N007 H00A 0.9100 . ?
N007 H00B 0.9100 . ?
N008 C00C 1.490(7) . ?
N008 C00E 1.505(8) . ?
N008 H00C 0.9100 . ?
N008 H00D 0.9100 . ?
C009 C00B 1.542(7) . ?
C009 H00E 0.9900 . ?
C009 H00F 0.9900 . ?
C00A C00B 1.541(7) . ?
C00A H00G 0.9900 . ?
C00A H00H 0.9900 . ?
C00B C00C 1.533(7) . ?
C00B C00D 1.541(7) . ?
C00C H00I 0.9900 . ?
C00C H00J 0.9900 . ?
C00E C00F 1.513(10) . ?
C00E H00K 0.9900 . ?
C00E H00L 0.9900 . ?
C00F C00G 1.527(9) . ?
C00F H00M 0.9900 . ?
C00F H00N 0.9900 . ?
C00G H00O 0.9900 . ?
C00G H00Q 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
C00A N006 H00P 109.5 . . ?
C00A N006 H00R 109.5 . . ?
H00P N006 H00R 109.5 . . ?
C00A N006 H00S 109.5 . . ?
H00P N006 H00S 109.5 . . ?
H00R N006 H00S 109.5 . . ?
C009 N007 C00G 115.3(5) . . ?
C009 N007 H00A 108.4 . . ?
C00G N007 H00A 108.4 . . ?
C009 N007 H00B 108.4 . . ?
C00G N007 H00B 108.4 . . ?
H00A N007 H00B 107.5 . . ?
C00C N008 C00E 119.3(4) . . ?
C00C N008 H00C 107.5 . . ?
C00E N008 H00C 107.5 . . ?
C00C N008 H00D 107.5 . . ?
C00E N008 H00D 107.5 . . ?
H00C N008 H00D 107.0 . . ?
N007 C009 C00B 116.5(4) . . ?
N007 C009 H00E 108.2 . . ?
C00B C009 H00E 108.2 . . ?
N007 C009 H00F 108.2 . . ?
C00B C009 H00F 108.2 . . ?
H00E C009 H00F 107.3 . . ?
N006 C00A C00B 113.8(4) . . ?
N006 C00A H00G 108.8 . . ?
C00B C00A H00G 108.8 . . ?
N006 C00A H00H 108.8 . . ?
C00B C00A H00H 108.8 . . ?
H00G C00A H00H 107.7 . . ?
C00C C00B C00A 102.3(4) . . ?
C00C C00B C00D 110.1(4) . . ?
C00A C00B C00D 109.9(4) . . ?
C00C C00B C009 114.7(4) . . ?
C00A C00B C009 111.8(4) . . ?
C00D C00B C009 108.0(4) . . ?
N008 C00C C00B 116.9(4) . . ?
N008 C00C H00I 108.1 . . ?
C00B C00C H00I 108.1 . . ?
N008 C00C H00J 108.1 . . ?
C00B C00C H00J 108.1 . . ?
H00I C00C H00J 107.3 . . ?
N008 C00E C00F 114.0(5) . . ?
N008 C00E H00K 108.7 . . ?
C00F C00E H00K 108.7 . . ?
N008 C00E H00L 108.7 . . ?
C00F C00E H00L 108.7 . . ?
H00K C00E H00L 107.6 . . ?
C00E C00F C00G 116.6(5) . . ?
C00E C00F H00M 108.1 . . ?
C00G C00F H00M 108.1 . . ?
C00E C00F H00N 108.1 . . ?
C00G C00F H00N 108.1 . . ?
H00M C00F H00N 107.3 . . ?
N007 C00G C00F 116.6(5) . . ?
N007 C00G H00O 108.1 . . ?
C00F C00G H00O 108.1 . . ?
N007 C00G H00Q 108.1 . . ?
C00F C00G H00Q 108.1 . . ?
H00O C00G H00Q 107.3 . . ?

_refine_diff_density_max         3.244
_refine_diff_density_min         -3.160
_refine_diff_density_rms         0.198

