# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_compound_6
_database_code_depnum_ccdc_archive 'CCDC 1409978'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H54 F3 I3 N6 O2 S2'
_chemical_formula_weight         1272.81

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.3644(3)
_cell_length_b                   13.44670(10)
_cell_length_c                   28.0955(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.0420(10)
_cell_angle_gamma                90
_cell_volume                     10312.33(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23736
_cell_measurement_theta_min      3.1910
_cell_measurement_theta_max      73.7180

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             5040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3489
_exptl_crystal_size_mid          0.2700
_exptl_crystal_size_min          0.1328
_exptl_absorpt_coefficient_mu    15.493
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_T_max  0.565
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 5.2977
_diffrn_reflns_number            37841
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.154
_diffrn_reflns_theta_max         73.824
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10289
_reflns_number_gt                9118
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0579P)²+24.7825P] 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         10289
_refine_ls_number_parameters     597
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.65941(14) 0.0682(3) 0.22105(12) 0.0430(8) Uani 1 1 d . . . . .
C2 C 0.69095(14) 0.1213(3) 0.19422(12) 0.0441(8) Uani 1 1 d . . . . .
C3 C 0.69131(13) 0.2243(3) 0.19254(13) 0.0444(8) Uani 1 1 d . . . . .
C4 C 0.65781(13) 0.2730(3) 0.21872(12) 0.0428(8) Uani 1 1 d . . . . .
C5 C 0.62539(13) 0.2247(3) 0.24641(12) 0.0406(7) Uani 1 1 d . . . . .
C6 C 0.62726(13) 0.1219(3) 0.24678(12) 0.0431(8) Uani 1 1 d . . . . .
C7 C 0.47112(18) 0.4973(4) 0.31828(18) 0.0656(12) Uani 1 1 d . . . . .
H7 H 0.4514 0.4738 0.2924 0.079 Uiso 1 1 calc R U . . .
C8 C 0.45646(16) 0.5823(3) 0.34109(15) 0.0552(10) Uani 1 1 d . . . . .
H8 H 0.4277 0.6148 0.3305 0.066 Uiso 1 1 calc R U . . .
C9 C 0.48485(13) 0.6183(3) 0.37970(12) 0.0425(7) Uani 1 1 d . . . . .
C10 C 0.52743(16) 0.5670(4) 0.39300(15) 0.0584(10) Uani 1 1 d . . . . .
H10 H 0.5481 0.5891 0.4185 0.070 Uiso 1 1 calc R U . . .
C11 C 0.53885(18) 0.4830(4) 0.36823(17) 0.0636(11) Uani 1 1 d . . . . .
H11 H 0.5674 0.4492 0.3781 0.076 Uiso 1 1 calc R U . . .
C12 C 0.47212(14) 0.7065(3) 0.40669(13) 0.0439(8) Uani 1 1 d . . . . .
C13 C 0.44027(13) 0.8540(3) 0.44030(13) 0.0443(8) Uani 1 1 d . . . . .
C14 C 0.41418(13) 0.9437(3) 0.45344(13) 0.0425(7) Uani 1 1 d . . . . .
C15 C 0.37519(14) 0.9830(3) 0.42469(13) 0.0489(9) Uani 1 1 d . . . . .
H15 H 0.3648 0.9507 0.3965 0.059 Uiso 1 1 calc R U . . .
C16 C 0.35199(15) 1.0680(3) 0.43719(14) 0.0539(9) Uani 1 1 d . . . . .
H16 H 0.3262 1.0932 0.4174 0.065 Uiso 1 1 calc R U . . .
C17 C 0.36663(14) 1.1173(3) 0.47933(14) 0.0475(8) Uani 1 1 d . . . . .
C18 C 0.40562(15) 1.0797(3) 0.50843(14) 0.0524(9) Uani 1 1 d . . . . .
H18 H 0.4159 1.1124 0.5365 0.063 Uiso 1 1 calc R U . . .
C19 C 0.42886(15) 0.9942(3) 0.49551(14) 0.0504(9) Uani 1 1 d . . . . .
H19 H 0.4549 0.9696 0.5151 0.060 Uiso 1 1 calc R U . . .
C20 C 0.35424(17) 1.2559(3) 0.53087(16) 0.0569(10) Uani 1 1 d . . . . .
H20A H 0.3878 1.2790 0.5304 0.068 Uiso 1 1 calc R U . . .
H20B H 0.3514 1.2155 0.5592 0.068 Uiso 1 1 calc R U . . .
C21 C 0.31962(17) 1.3426(3) 0.53084(16) 0.0570(10) Uani 1 1 d . . . . .
H21A H 0.2864 1.3176 0.5306 0.068 Uiso 1 1 calc R U . . .
H21B H 0.3223 1.3805 0.5018 0.068 Uiso 1 1 calc R U . . .
C23 C 0.32889(17) 1.4111(3) 0.57297(17) 0.0578(10) Uani 1 1 d . . . . .
H23A H 0.3620 1.4367 0.5731 0.069 Uiso 1 1 calc R U . . .
H23B H 0.3263 1.3734 0.6021 0.069 Uiso 1 1 calc R U . . .
C24 C 0.29358(15) 1.4977(3) 0.57259(16) 0.0556(10) Uani 1 1 d . . . . .
H24A H 0.2605 1.4714 0.5722 0.067 Uiso 1 1 calc R U . . .
H24B H 0.2961 1.5345 0.5432 0.067 Uiso 1 1 calc R U . . .
C25 C 0.30097(15) 1.5695(3) 0.61395(16) 0.0531(9) Uani 1 1 d . . . . .
H25A H 0.3334 1.5985 0.6137 0.064 Uiso 1 1 calc R U . . .
H25B H 0.2994 1.5330 0.6436 0.064 Uiso 1 1 calc R U . . .
C26 C 0.26333(15) 1.6523(3) 0.61240(15) 0.0536(9) Uani 1 1 d . . . . .
H26A H 0.2662 1.6901 0.5833 0.064 Uiso 1 1 calc R U . . .
H26B H 0.2310 1.6226 0.6106 0.064 Uiso 1 1 calc R U . . .
C27 C 0.26726(15) 1.7232(3) 0.65398(15) 0.0533(9) Uani 1 1 d . . . . .
H27A H 0.2996 1.7530 0.6561 0.064 Uiso 1 1 calc R U . . .
H27B H 0.2637 1.6862 0.6832 0.064 Uiso 1 1 calc R U . . .
C28 C 0.22913(18) 1.8054(4) 0.65015(18) 0.0619(11) Uani 1 1 d . . . . .
H28A H 0.2344 1.8453 0.6222 0.074 Uiso 1 1 calc R U . . .
H28B H 0.1969 1.7754 0.6454 0.074 Uiso 1 1 calc R U . . .
C29 C 0.2299(3) 1.8726(5) 0.6931(2) 0.0907(18) Uani 1 1 d . . . . .
H29A H 0.2255 1.8336 0.7211 0.136 Uiso 1 1 calc R U . . .
H29B H 0.2039 1.9204 0.6889 0.136 Uiso 1 1 calc R U . . .
H29C H 0.2608 1.9067 0.6967 0.136 Uiso 1 1 calc R U . . .
C30 C 0.67084(16) 0.0003(4) 0.37772(16) 0.0594(11) Uani 1 1 d . . . . .
H30 H 0.6607 -0.0226 0.3474 0.071 Uiso 1 1 calc R U . . .
C31 C 0.64931(15) 0.0856(3) 0.39351(14) 0.0518(9) Uani 1 1 d . . . . .
H31 H 0.6254 0.1187 0.3744 0.062 Uiso 1 1 calc R U . . .
C32 C 0.66430(13) 0.1211(3) 0.43878(13) 0.0434(8) Uani 1 1 d . . . . .
C33 C 0.70081(16) 0.0687(3) 0.46483(15) 0.0552(10) Uani 1 1 d . . . . .
H33 H 0.7125 0.0908 0.4949 0.066 Uiso 1 1 calc R U . . .
C34 C 0.71955(17) -0.0160(4) 0.44582(17) 0.0625(11) Uani 1 1 d . . . . .
H34 H 0.7437 -0.0507 0.4639 0.075 Uiso 1 1 calc R U . . .
C35 C 0.64143(13) 0.2111(3) 0.45702(13) 0.0434(8) Uani 1 1 d . . . . .
C36 C 0.61505(13) 0.3558(3) 0.49728(12) 0.0419(7) Uani 1 1 d . . . . .
C37 C 0.60631(13) 0.4412(3) 0.52739(12) 0.0411(7) Uani 1 1 d . . . . .
C38 C 0.56696(14) 0.5035(3) 0.51547(13) 0.0484(9) Uani 1 1 d . . . . .
H38 H 0.5461 0.4885 0.4889 0.058 Uiso 1 1 calc R U . . .
C39 C 0.55792(14) 0.5869(3) 0.54182(14) 0.0496(9) Uani 1 1 d . . . . .
H39 H 0.5320 0.6288 0.5324 0.060 Uiso 1 1 calc R U . . .
C40 C 0.58777(14) 0.6081(3) 0.58264(13) 0.0444(8) Uani 1 1 d . . . . .
C41 C 0.62694(15) 0.5450(3) 0.59540(14) 0.0519(9) Uani 1 1 d . . . . .
H41 H 0.6470 0.5582 0.6228 0.062 Uiso 1 1 calc R U . . .
C42 C 0.63617(14) 0.4640(3) 0.56807(14) 0.0488(9) Uani 1 1 d . . . . .
H42 H 0.6628 0.4234 0.5768 0.059 Uiso 1 1 calc R U . . .
C43 C 0.54194(15) 0.7536(3) 0.59973(14) 0.0493(9) Uani 1 1 d . . . . .
H43A H 0.5110 0.7180 0.5981 0.059 Uiso 1 1 calc R U . . .
H43B H 0.5459 0.7839 0.5689 0.059 Uiso 1 1 calc R U . . .
C44 C 0.54265(15) 0.8320(3) 0.63808(14) 0.0499(9) Uani 1 1 d . . . . .
H44A H 0.5747 0.8630 0.6412 0.060 Uiso 1 1 calc R U . . .
H44B H 0.5369 0.8010 0.6683 0.060 Uiso 1 1 calc R U . . .
C45 C 0.50401(14) 0.9113(3) 0.62680(14) 0.0473(8) Uani 1 1 d . . . . .
H45A H 0.5095 0.9408 0.5961 0.057 Uiso 1 1 calc R U . . .
H45B H 0.4720 0.8799 0.6240 0.057 Uiso 1 1 calc R U . . .
C46 C 0.50366(15) 0.9933(3) 0.66388(14) 0.0494(9) Uani 1 1 d . . . . .
H46A H 0.4981 0.9639 0.6946 0.059 Uiso 1 1 calc R U . . .
H46B H 0.5356 1.0248 0.6666 0.059 Uiso 1 1 calc R U . . .
C47 C 0.46504(14) 1.0722(3) 0.65244(14) 0.0482(8) Uani 1 1 d . . . . .
H47A H 0.4333 1.0401 0.6478 0.058 Uiso 1 1 calc R U . . .
H47B H 0.4717 1.1040 0.6226 0.058 Uiso 1 1 calc R U . . .
C48 C 0.46235(15) 1.1517(3) 0.69060(14) 0.0508(9) Uani 1 1 d . . . . .
H48A H 0.4933 1.1872 0.6935 0.061 Uiso 1 1 calc R U . . .
H48B H 0.4583 1.1194 0.7209 0.061 Uiso 1 1 calc R U . . .
C49 C 0.42113(16) 1.2266(3) 0.68114(15) 0.0526(9) Uani 1 1 d . . . . .
H49A H 0.4251 1.2594 0.6509 0.063 Uiso 1 1 calc R U . . .
H49B H 0.3901 1.1916 0.6785 0.063 Uiso 1 1 calc R U . . .
C50 C 0.4197(2) 1.3048(3) 0.72005(18) 0.0632(12) Uani 1 1 d . . . . .
H50A H 0.4183 1.2715 0.7505 0.076 Uiso 1 1 calc R U . . .
H50B H 0.4499 1.3427 0.7211 0.076 Uiso 1 1 calc R U . . .
C51 C 0.3773(2) 1.3754(5) 0.7134(2) 0.0841(16) Uani 1 1 d . . . . .
H51A H 0.3785 1.4091 0.6834 0.126 Uiso 1 1 calc R U . . .
H51B H 0.3790 1.4233 0.7388 0.126 Uiso 1 1 calc R U . . .
H51C H 0.3471 1.3390 0.7137 0.126 Uiso 1 1 calc R U . . .
F1 F 0.59623(10) 0.07200(18) 0.27303(9) 0.0600(6) Uani 1 1 d . . . . .
F2 F 0.72291(10) 0.0708(2) 0.16932(9) 0.0646(7) Uani 1 1 d . . . . .
F3 F 0.65712(9) 0.37271(18) 0.21789(9) 0.0599(6) Uani 1 1 d . . . . .
I1 I 0.66102(2) -0.08566(2) 0.22378(2) 0.07021(11) Uani 1 1 d . . . . .
I2 I 0.73912(2) 0.30323(2) 0.15127(2) 0.05514(9) Uani 1 1 d . . . . .
I3 I 0.57456(2) 0.30361(2) 0.28392(2) 0.05042(8) Uani 1 1 d . . . . .
N4 N 0.70494(14) -0.0515(3) 0.40259(14) 0.0595(9) Uani 1 1 d . . . . .
N5 N 0.60326(14) 0.2523(3) 0.43541(13) 0.0596(9) Uani 1 1 d . . . . .
N6 N 0.58820(14) 0.3348(3) 0.45829(13) 0.0604(9) Uani 1 1 d . . . . .
N1 N 0.51196(15) 0.4472(3) 0.33132(14) 0.0607(9) Uani 1 1 d . . . . .
N2 N 0.49730(14) 0.7356(3) 0.44515(13) 0.0587(9) Uani 1 1 d . . . . .
N3 N 0.47901(14) 0.8197(3) 0.46457(13) 0.0598(9) Uani 1 1 d . . . . .
O1 O 0.34066(12) 1.1994(2) 0.48873(12) 0.0632(8) Uani 1 1 d . . . . .
O2 O 0.58190(11) 0.6865(2) 0.61204(10) 0.0535(7) Uani 1 1 d . . . . .
S1 S 0.42302(3) 0.78228(7) 0.39079(3) 0.0463(2) Uani 1 1 d . . . . .
S2 S 0.66226(3) 0.27141(7) 0.50870(3) 0.0468(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 C6 1.382(5) . ?
C1 C2 1.384(5) . ?
C1 I1 2.070(4) . ?
C2 F2 1.342(4) . ?
C2 C3 1.386(6) . ?
C3 C4 1.380(5) . ?
C3 I2 2.097(4) . ?
C4 F3 1.341(5) . ?
C4 C5 1.382(5) . ?
C5 C6 1.383(5) . ?
C5 I3 2.092(4) . ?
C6 F1 1.343(4) . ?
C7 N1 1.334(6) . ?
C7 C8 1.384(6) . ?
C8 C9 1.377(5) . ?
C9 C10 1.382(6) . ?
C9 C12 1.464(5) . ?
C10 C11 1.374(7) . ?
C11 N1 1.320(6) . ?
C12 N2 1.300(5) . ?
C12 S1 1.720(4) . ?
C13 N3 1.304(5) . ?
C13 C14 1.462(6) . ?
C13 S1 1.731(4) . ?
C14 C15 1.396(5) . ?
C14 C19 1.398(5) . ?
C15 C16 1.365(6) . ?
C16 C17 1.391(5) . ?
C17 O1 1.350(5) . ?
C17 C18 1.392(6) . ?
C18 C19 1.375(6) . ?
C20 O1 1.433(5) . ?
C20 C21 1.502(6) . ?
C21 C23 1.507(6) . ?
C23 C24 1.512(6) . ?
C24 C25 1.513(6) . ?
C25 C26 1.515(6) . ?
C26 C27 1.506(6) . ?
C27 C28 1.518(6) . ?
C28 C29 1.507(7) . ?
C30 N4 1.323(6) . ?
C30 C31 1.377(6) . ?
C31 C32 1.393(5) . ?
C32 C33 1.388(6) . ?
C32 C35 1.472(5) . ?
C33 C34 1.373(6) . ?
C34 N4 1.339(6) . ?
C35 N5 1.295(5) . ?
C35 S2 1.725(4) . ?
C36 N6 1.306(5) . ?
C36 C37 1.456(5) . ?
C36 S2 1.732(4) . ?
C37 C38 1.386(5) . ?
C37 C42 1.391(5) . ?
C38 C39 1.375(6) . ?
C39 C40 1.390(5) . ?
C40 O2 1.355(5) . ?
C40 C41 1.394(5) . ?
C41 C42 1.367(6) . ?
C43 O2 1.441(5) . ?
C43 C44 1.507(6) . ?
C44 C45 1.519(6) . ?
C45 C46 1.517(5) . ?
C46 C47 1.516(6) . ?
C47 C48 1.519(5) . ?
C48 C49 1.522(6) . ?
C49 C50 1.519(6) . ?
C50 C51 1.502(7) . ?
N5 N6 1.361(5) . ?
N2 N3 1.366(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.3(4) . . ?
C6 C1 I1 121.1(3) . . ?
C2 C1 I1 121.6(3) . . ?
F2 C2 C1 118.5(3) . . ?
F2 C2 C3 118.8(3) . . ?
C1 C2 C3 122.7(3) . . ?
C4 C3 C2 116.7(3) . . ?
C4 C3 I2 121.2(3) . . ?
C2 C3 I2 122.1(3) . . ?
F3 C4 C3 118.3(3) . . ?
F3 C4 C5 118.1(3) . . ?
C3 C4 C5 123.6(4) . . ?
C4 C5 C6 116.7(3) . . ?
C4 C5 I3 121.4(3) . . ?
C6 C5 I3 121.9(3) . . ?
F1 C6 C1 118.4(3) . . ?
F1 C6 C5 118.6(3) . . ?
C1 C6 C5 122.9(3) . . ?
N1 C7 C8 123.7(4) . . ?
C9 C8 C7 119.3(4) . . ?
C8 C9 C10 117.1(4) . . ?
C8 C9 C12 123.4(4) . . ?
C10 C9 C12 119.4(3) . . ?
C11 C10 C9 119.4(4) . . ?
N1 C11 C10 124.3(4) . . ?
N2 C12 C9 122.9(4) . . ?
N2 C12 S1 113.4(3) . . ?
C9 C12 S1 123.8(3) . . ?
N3 C13 C14 123.6(3) . . ?
N3 C13 S1 112.9(3) . . ?
C14 C13 S1 123.5(3) . . ?
C15 C14 C19 117.9(4) . . ?
C15 C14 C13 122.2(3) . . ?
C19 C14 C13 119.9(3) . . ?
C16 C15 C14 121.2(4) . . ?
C15 C16 C17 120.4(4) . . ?
O1 C17 C16 115.6(4) . . ?
O1 C17 C18 125.0(4) . . ?
C16 C17 C18 119.3(4) . . ?
C19 C18 C17 119.9(4) . . ?
C18 C19 C14 121.3(4) . . ?
O1 C20 C21 106.5(3) . . ?
C20 C21 C23 113.7(4) . . ?
C21 C23 C24 113.1(4) . . ?
C23 C24 C25 115.8(4) . . ?
C24 C25 C26 113.1(4) . . ?
C27 C26 C25 115.6(4) . . ?
C26 C27 C28 113.3(4) . . ?
C29 C28 C27 114.1(4) . . ?
N4 C30 C31 124.7(4) . . ?
C30 C31 C32 118.3(4) . . ?
C33 C32 C31 117.6(4) . . ?
C33 C32 C35 122.8(3) . . ?
C31 C32 C35 119.6(4) . . ?
C34 C33 C32 119.4(4) . . ?
N4 C34 C33 123.5(4) . . ?
N5 C35 C32 122.5(3) . . ?
N5 C35 S2 113.7(3) . . ?
C32 C35 S2 123.8(3) . . ?
N6 C36 C37 123.5(3) . . ?
N6 C36 S2 112.4(3) . . ?
C37 C36 S2 124.1(3) . . ?
C38 C37 C42 117.8(3) . . ?
C38 C37 C36 119.5(3) . . ?
C42 C37 C36 122.6(3) . . ?
C39 C38 C37 121.9(3) . . ?
C38 C39 C40 119.6(4) . . ?
O2 C40 C39 125.1(4) . . ?
O2 C40 C41 116.0(3) . . ?
C39 C40 C41 118.9(4) . . ?
C42 C41 C40 120.7(3) . . ?
C41 C42 C37 121.0(4) . . ?
O2 C43 C44 107.2(3) . . ?
C43 C44 C45 111.6(3) . . ?
C46 C45 C44 113.9(3) . . ?
C47 C46 C45 113.6(3) . . ?
C46 C47 C48 114.2(3) . . ?
C47 C48 C49 114.5(3) . . ?
C50 C49 C48 112.9(4) . . ?
C51 C50 C49 114.0(4) . . ?
C30 N4 C34 116.5(4) . . ?
C35 N5 N6 112.9(3) . . ?
C36 N6 N5 113.7(3) . . ?
C11 N1 C7 116.2(4) . . ?
C12 N2 N3 113.1(3) . . ?
C13 N3 N2 113.0(3) . . ?
C17 O1 C20 119.1(3) . . ?
C40 O2 C43 117.5(3) . . ?
C12 S1 C13 87.56(19) . . ?
C35 S2 C36 87.37(18) . . ?

_refine_diff_density_max         1.229
_refine_diff_density_min         -1.842
_refine_diff_density_rms         0.112




####################################################################### 
# 
# 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_compound_5
_database_code_depnum_ccdc_archive 'CCDC 1409979'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 F3 I3 N3 O2'
_chemical_formula_weight         889.25

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.4878(10)
_cell_length_b                   12.3896(11)
_cell_length_c                   12.7932(12)
_cell_angle_alpha                78.982(8)
_cell_angle_beta                 82.201(8)
_cell_angle_gamma                81.597(8)
_cell_volume                     1604.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5384
_cell_measurement_theta_min      3.5320
_cell_measurement_theta_max      73.0490

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5606
_exptl_crystal_size_mid          0.5116
_exptl_crystal_size_min          0.3621
_exptl_absorpt_coefficient_mu    23.357
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.018
_exptl_absorpt_correction_T_max  0.294
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            14866
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_av_R_equivalents  0.1237
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.542
_diffrn_reflns_theta_max         73.722
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6265
_reflns_number_gt                4890
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6265
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.1410
_refine_ls_wR_factor_ref         0.3535
_refine_ls_wR_factor_gt          0.3318
_refine_ls_goodness_of_fit_ref   1.277
_refine_ls_restrained_S_all      1.277
_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 0.0310(13) 0.2159(10) 0.1347(10) 0.072(3) Uani 1 1 d . . . . .
C2 C 0.0856(14) 0.2599(9) 0.2089(10) 0.073(3) Uani 1 1 d . . . . .
C3 C 0.1878(14) 0.2057(11) 0.2646(9) 0.072(3) Uani 1 1 d . . . . .
C4 C 0.2273(12) 0.0961(10) 0.2509(9) 0.070(3) Uani 1 1 d . . . . .
C5 C 0.1718(13) 0.0514(9) 0.1795(9) 0.069(2) Uani 1 1 d . . . . .
C6 C 0.0756(16) 0.1115(11) 0.1258(12) 0.081(3) Uani 1 1 d . . . . .
C7 C 0.4552(18) 0.2981(15) 0.5863(14) 0.093(4) Uani 1 1 d . . . . .
H7 H 0.4753 0.2294 0.5649 0.112 Uiso 1 1 calc R U . . .
C8 C 0.5187(16) 0.3179(12) 0.6687(13) 0.084(3) Uani 1 1 d . . . . .
H8 H 0.5790 0.2634 0.7011 0.100 Uiso 1 1 calc R U . . .
C9 C 0.4909(12) 0.4188(9) 0.7013(9) 0.066(2) Uani 1 1 d . . . . .
C10 C 0.3969(16) 0.4946(13) 0.6512(15) 0.091(4) Uani 1 1 d . . . . .
H10 H 0.3718 0.5629 0.6728 0.109 Uiso 1 1 calc R U . . .
C11 C 0.342(2) 0.4682(19) 0.5701(16) 0.108(6) Uani 1 1 d . . . . .
H11 H 0.2817 0.5217 0.5361 0.130 Uiso 1 1 calc R U . . .
C12 C 0.5570(13) 0.4409(8) 0.7859(9) 0.067(2) Uani 1 1 d . . . . .
C13 C 0.6135(12) 0.5327(10) 0.8925(9) 0.067(2) Uani 1 1 d . . . . .
C14 C 0.6166(11) 0.6270(10) 0.9442(9) 0.065(2) Uani 1 1 d . . . . .
C15 C 0.7050(14) 0.6196(10) 1.0173(12) 0.076(3) Uani 1 1 d . . . . .
H15 H 0.7616 0.5548 1.0321 0.091 Uiso 1 1 calc R U . . .
C16 C 0.7101(14) 0.7057(11) 1.0679(12) 0.079(3) Uani 1 1 d . . . . .
H16 H 0.7667 0.6982 1.1195 0.095 Uiso 1 1 calc R U . . .
C17 C 0.6313(14) 0.8043(10) 1.0425(10) 0.073(3) Uani 1 1 d . . . . .
C18 C 0.5459(14) 0.8135(10) 0.9674(10) 0.074(3) Uani 1 1 d . . . . .
H18 H 0.4933 0.8800 0.9498 0.089 Uiso 1 1 calc R U . . .
C19 C 0.5375(13) 0.7269(9) 0.9186(10) 0.071(3) Uani 1 1 d . . . . .
H19 H 0.4792 0.7342 0.8683 0.085 Uiso 1 1 calc R U . . .
C20 C 0.7177(18) 0.8893(12) 1.1664(12) 0.086(3) Uani 1 1 d . . . . .
H20A H 0.8078 0.8775 1.1368 0.103 Uiso 1 1 calc R U . . .
H20B H 0.7010 0.8281 1.2241 0.103 Uiso 1 1 calc R U . . .
C21 C 0.6909(19) 0.9963(13) 1.2076(14) 0.091(4) Uani 1 1 d . . . . .
H21A H 0.5999 1.0093 1.2342 0.110 Uiso 1 1 calc R U . . .
H21B H 0.7106 1.0569 1.1502 0.110 Uiso 1 1 calc R U . . .
C22 C 0.775(2) 0.9910(14) 1.2981(13) 0.093(4) Uani 1 1 d . . . . .
H22A H 0.8652 0.9752 1.2717 0.111 Uiso 1 1 calc R U . . .
H22B H 0.7530 0.9312 1.3559 0.111 Uiso 1 1 calc R U . . .
C24 C 0.753(2) 1.1023(15) 1.3419(15) 0.099(5) Uani 1 1 d . . . . .
H24A H 0.7688 1.1631 1.2834 0.119 Uiso 1 1 calc R U . . .
H24B H 0.6641 1.1155 1.3735 0.119 Uiso 1 1 calc R U . . .
C25 C 0.8437(19) 1.0979(13) 1.4249(13) 0.090(4) Uani 1 1 d . . . . .
H25A H 0.9322 1.0797 1.3940 0.108 Uiso 1 1 calc R U . . .
H25B H 0.8246 1.0392 1.4846 0.108 Uiso 1 1 calc R U . . .
C26 C 0.8334(17) 1.2065(14) 1.4667(14) 0.089(4) Uani 1 1 d . . . . .
H26A H 0.7457 1.2237 1.4998 0.107 Uiso 1 1 calc R U . . .
H26B H 0.8501 1.2657 1.4069 0.107 Uiso 1 1 calc R U . . .
C27 C 0.9296(17) 1.2016(12) 1.5491(14) 0.088(4) Uani 1 1 d . . . . .
H27A H 0.9106 1.1439 1.6098 0.105 Uiso 1 1 calc R U . . .
H27B H 1.0167 1.1814 1.5166 0.105 Uiso 1 1 calc R U . . .
C28 C 0.9253(17) 1.3088(14) 1.5890(15) 0.090(4) Uani 1 1 d . . . . .
H28A H 0.9414 1.3669 1.5280 0.108 Uiso 1 1 calc R U . . .
H28B H 0.8388 1.3277 1.6233 0.108 Uiso 1 1 calc R U . . .
C29 C 1.0155(17) 1.3066(14) 1.6622(16) 0.095(4) Uani 1 1 d . . . . .
H29A H 1.1021 1.2916 1.6262 0.114 Uiso 1 1 calc R U . . .
H29B H 1.0028 1.2453 1.7207 0.114 Uiso 1 1 calc R U . . .
C30 C 1.009(3) 1.4103(14) 1.7090(19) 0.115(6) Uani 1 1 d . . . . .
H30A H 1.0733 1.3999 1.7581 0.172 Uiso 1 1 calc R U . . .
H30B H 0.9246 1.4257 1.7462 0.172 Uiso 1 1 calc R U . . .
H30C H 1.0258 1.4714 1.6524 0.172 Uiso 1 1 calc R U . . .
F1 F 0.0448(12) 0.3674(7) 0.2212(10) 0.106(3) Uani 1 1 d . . . . .
F2 F 0.3233(9) 0.0388(8) 0.3042(8) 0.089(2) Uani 1 1 d . . . . .
F3 F 0.0267(10) 0.0669(7) 0.0555(8) 0.095(2) Uani 1 1 d . . . . .
I1 I -0.11270(10) 0.31030(7) 0.04600(8) 0.0898(4) Uani 1 1 d . . . . .
I2 I 0.26448(9) 0.27720(8) 0.37351(6) 0.0834(4) Uani 1 1 d . . . . .
I3 I 0.24318(11) -0.11139(7) 0.15326(8) 0.0877(4) Uani 1 1 d . . . . .
N1 N 0.3674(14) 0.3716(15) 0.5365(11) 0.098(4) Uani 1 1 d . . . . .
N2 N 0.6451(13) 0.3752(9) 0.8379(9) 0.078(3) Uani 1 1 d . . . . .
N3 N 0.6797(12) 0.4363(9) 0.9078(10) 0.079(3) Uani 1 1 d . . . . .
O1 O 0.5291(8) 0.5407(6) 0.8171(6) 0.0657(16) Uani 1 1 d . . . . .
O2 O 0.6355(12) 0.8953(8) 1.0860(9) 0.089(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.330(19) . ?
C1 C2 1.401(17) . ?
C1 I1 2.090(12) . ?
C2 F1 1.369(13) . ?
C2 C3 1.39(2) . ?
C3 C4 1.397(18) . ?
C3 I2 2.087(11) . ?
C4 F2 1.332(15) . ?
C4 C5 1.383(15) . ?
C5 C6 1.35(2) . ?
C5 I3 2.118(11) . ?
C6 F3 1.333(17) . ?
C7 N1 1.33(3) . ?
C7 C8 1.40(2) . ?
C8 C9 1.371(18) . ?
C9 C10 1.39(2) . ?
C9 C12 1.449(16) . ?
C10 C11 1.37(2) . ?
C11 N1 1.33(3) . ?
C12 N2 1.303(17) . ?
C12 O1 1.352(13) . ?
C13 N3 1.284(17) . ?
C13 O1 1.376(13) . ?
C13 C14 1.455(17) . ?
C14 C15 1.386(18) . ?
C14 C19 1.395(17) . ?
C15 C16 1.360(16) . ?
C16 C17 1.380(19) . ?
C17 O2 1.358(15) . ?
C17 C18 1.378(19) . ?
C18 C19 1.359(17) . ?
C20 O2 1.415(18) . ?
C20 C21 1.494(19) . ?
C21 C22 1.53(2) . ?
C22 C24 1.56(2) . ?
C24 C25 1.51(2) . ?
C25 C26 1.525(19) . ?
C26 C27 1.54(2) . ?
C27 C28 1.50(2) . ?
C28 C29 1.41(2) . ?
C29 C30 1.51(2) . ?
N2 N3 1.390(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 115.8(12) . . ?
C6 C1 I1 123.1(10) . . ?
C2 C1 I1 121.1(9) . . ?
F1 C2 C3 116.5(11) . . ?
F1 C2 C1 118.8(12) . . ?
C3 C2 C1 124.4(11) . . ?
C2 C3 C4 115.4(10) . . ?
C2 C3 I2 122.2(9) . . ?
C4 C3 I2 122.2(9) . . ?
F2 C4 C5 121.5(12) . . ?
F2 C4 C3 118.2(10) . . ?
C5 C4 C3 120.2(11) . . ?
C6 C5 C4 120.3(12) . . ?
C6 C5 I3 120.6(9) . . ?
C4 C5 I3 119.0(10) . . ?
C1 C6 F3 117.6(13) . . ?
C1 C6 C5 123.5(13) . . ?
F3 C6 C5 118.8(12) . . ?
N1 C7 C8 124.0(15) . . ?
C9 C8 C7 119.0(14) . . ?
C8 C9 C10 117.0(12) . . ?
C8 C9 C12 119.6(12) . . ?
C10 C9 C12 123.4(11) . . ?
C11 C10 C9 119.6(15) . . ?
N1 C11 C10 124.5(16) . . ?
N2 C12 O1 113.1(10) . . ?
N2 C12 C9 127.8(10) . . ?
O1 C12 C9 119.1(10) . . ?
N3 C13 O1 111.5(10) . . ?
N3 C13 C14 128.9(11) . . ?
O1 C13 C14 119.5(11) . . ?
C15 C14 C19 118.7(11) . . ?
C15 C14 C13 119.2(11) . . ?
C19 C14 C13 122.0(11) . . ?
C16 C15 C14 120.9(12) . . ?
C15 C16 C17 120.0(12) . . ?
O2 C17 C18 117.4(12) . . ?
O2 C17 C16 123.3(12) . . ?
C18 C17 C16 119.4(11) . . ?
C19 C18 C17 121.0(12) . . ?
C18 C19 C14 119.8(11) . . ?
O2 C20 C21 107.8(14) . . ?
C20 C21 C22 109.3(14) . . ?
C21 C22 C24 111.4(15) . . ?
C25 C24 C22 110.2(15) . . ?
C24 C25 C26 113.0(14) . . ?
C25 C26 C27 112.3(15) . . ?
C28 C27 C26 113.7(14) . . ?
C29 C28 C27 114.4(14) . . ?
C28 C29 C30 116.1(16) . . ?
C11 N1 C7 115.8(13) . . ?
C12 N2 N3 105.3(10) . . ?
C13 N3 N2 107.8(10) . . ?
C12 O1 C13 102.3(9) . . ?
C17 O2 C20 119.8(12) . . ?

_refine_diff_density_max         3.576
_refine_diff_density_min         -3.185
_refine_diff_density_rms         0.439



####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1409980'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H27 F3 I3 N3 O2'
_chemical_formula_weight         875.22

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.5328(3)
_cell_length_b                   11.9482(3)
_cell_length_c                   13.9164(3)
_cell_angle_alpha                82.274(2)
_cell_angle_beta                 85.796(2)
_cell_angle_gamma                87.527(2)
_cell_volume                     1565.57(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10402
_cell_measurement_theta_min      3.6930
_cell_measurement_theta_max      73.2150

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7904
_exptl_crystal_size_mid          0.3206
_exptl_crystal_size_min          0.1523
_exptl_absorpt_coefficient_mu    23.922
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.065
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            16642
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.212
_diffrn_reflns_theta_max         73.312
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6127
_reflns_number_gt                5499
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1135P)²+1.0881P] 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         6127
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.4614(6) 0.7695(5) 1.3607(4) 0.0470(11) Uani 1 1 d . . . . .
C2 C 0.4030(6) 0.7307(5) 1.2826(4) 0.0488(12) Uani 1 1 d . . . . .
C3 C 0.3086(6) 0.7939(5) 1.2250(4) 0.0473(11) Uani 1 1 d . . . . .
C4 C 0.2731(6) 0.9026(5) 1.2468(4) 0.0469(11) Uani 1 1 d . . . . .
C5 C 0.3276(6) 0.9448(5) 1.3225(4) 0.0439(11) Uani 1 1 d . . . . .
C6 C 0.4204(6) 0.8768(4) 1.3778(4) 0.0448(11) Uani 1 1 d . . . . .
C7 C 0.0315(9) 0.7150(7) 0.8962(6) 0.0713(18) Uani 1 1 d . . . . .
H7 H 0.0133 0.7860 0.9155 0.086 Uiso 1 1 calc R U . . .
C8 C -0.0313(8) 0.6906(6) 0.8170(5) 0.0656(17) Uani 1 1 d . . . . .
H8 H -0.0918 0.7433 0.7845 0.079 Uiso 1 1 calc R U . . .
C9 C -0.0035(6) 0.5853(5) 0.7854(4) 0.0478(11) Uani 1 1 d . . . . .
C10 C 0.0860(8) 0.5101(6) 0.8372(6) 0.0679(17) Uani 1 1 d . . . . .
H10 H 0.1087 0.4391 0.8190 0.081 Uiso 1 1 calc R U . . .
C11 C 0.1408(10) 0.5450(7) 0.9177(7) 0.081(2) Uani 1 1 d . . . . .
H11 H 0.1995 0.4938 0.9536 0.097 Uiso 1 1 calc R U . . .
C12 C -0.0715(6) 0.5574(5) 0.7012(4) 0.0461(11) Uani 1 1 d . . . . .
C13 C -0.1238(5) 0.4579(4) 0.5933(4) 0.0420(10) Uani 1 1 d . . . . .
C14 C -0.1263(5) 0.3614(4) 0.5422(4) 0.0423(10) Uani 1 1 d . . . . .
C15 C -0.2100(6) 0.3648(5) 0.4639(5) 0.0512(12) Uani 1 1 d . . . . .
H15 H -0.2624 0.4305 0.4448 0.061 Uiso 1 1 calc R U . . .
C16 C -0.2174(6) 0.2738(5) 0.4141(5) 0.0517(12) Uani 1 1 d . . . . .
H16 H -0.2746 0.2777 0.3623 0.062 Uiso 1 1 calc R U . . .
C17 C -0.1386(6) 0.1759(4) 0.4418(4) 0.0469(11) Uani 1 1 d . . . . .
C18 C -0.0533(6) 0.1703(4) 0.5193(4) 0.0494(12) Uani 1 1 d . . . . .
H18 H -0.0004 0.1046 0.5376 0.059 Uiso 1 1 calc R U . . .
C19 C -0.0472(5) 0.2621(4) 0.5691(4) 0.0448(11) Uani 1 1 d . . . . .
H19 H 0.0099 0.2581 0.6210 0.054 Uiso 1 1 calc R U . . .
C20 C -0.2260(7) 0.0823(5) 0.3177(5) 0.0585(14) Uani 1 1 d . . . . .
H20A H -0.2031 0.1450 0.2680 0.070 Uiso 1 1 calc R U . . .
H20B H -0.3243 0.0908 0.3399 0.070 Uiso 1 1 calc R U . . .
C21 C -0.2002(8) -0.0285(6) 0.2768(6) 0.0642(16) Uani 1 1 d . . . . .
H21A H -0.2298 -0.0905 0.3254 0.077 Uiso 1 1 calc R U . . .
H21B H -0.1004 -0.0396 0.2601 0.077 Uiso 1 1 calc R U . . .
C22 C -0.2820(9) -0.0278(6) 0.1863(6) 0.0663(16) Uani 1 1 d . . . . .
H22A H -0.3809 -0.0124 0.2030 0.080 Uiso 1 1 calc R U . . .
H22B H -0.2494 0.0330 0.1375 0.080 Uiso 1 1 calc R U . . .
C23 C -0.2667(9) -0.1386(7) 0.1431(6) 0.0704(18) Uani 1 1 d . . . . .
H23A H -0.3001 -0.1993 0.1916 0.085 Uiso 1 1 calc R U . . .
H23B H -0.1678 -0.1543 0.1268 0.085 Uiso 1 1 calc R U . . .
C24 C -0.3477(10) -0.1371(7) 0.0523(6) 0.0746(19) Uani 1 1 d . . . . .
H24A H -0.4436 -0.1104 0.0663 0.089 Uiso 1 1 calc R U . . .
H24B H -0.3053 -0.0834 0.0010 0.089 Uiso 1 1 calc R U . . .
C25 C -0.3514(9) -0.2498(7) 0.0158(6) 0.0709(18) Uani 1 1 d . . . . .
H25A H -0.3967 -0.3030 0.0662 0.085 Uiso 1 1 calc R U . . .
H25B H -0.2556 -0.2777 0.0035 0.085 Uiso 1 1 calc R U . . .
C26 C -0.4279(9) -0.2461(7) -0.0756(5) 0.0707(18) Uani 1 1 d . . . . .
H26A H -0.3782 -0.1975 -0.1273 0.085 Uiso 1 1 calc R U . . .
H26B H -0.5212 -0.2124 -0.0648 0.085 Uiso 1 1 calc R U . . .
C27 C -0.4424(12) -0.3609(8) -0.1089(8) 0.092(3) Uani 1 1 d . . . . .
H27A H -0.4918 -0.4097 -0.0572 0.110 Uiso 1 1 calc R U . . .
H27B H -0.3492 -0.3944 -0.1202 0.110 Uiso 1 1 calc R U . . .
C28 C -0.5208(12) -0.3563(9) -0.2012(8) 0.094(3) Uani 1 1 d . . . . .
H28A H -0.5262 -0.4313 -0.2180 0.142 Uiso 1 1 calc R U . . .
H28B H -0.4714 -0.3098 -0.2534 0.142 Uiso 1 1 calc R U . . .
H28C H -0.6141 -0.3250 -0.1903 0.142 Uiso 1 1 calc R U . . .
F1 F 0.4385(5) 0.6255(3) 1.2637(3) 0.0749(12) Uani 1 1 d . . . . .
F2 F 0.1829(4) 0.9663(3) 1.1917(3) 0.0659(9) Uani 1 1 d . . . . .
F3 F 0.4726(4) 0.9171(3) 1.4520(3) 0.0628(9) Uani 1 1 d . . . . .
I1 I 0.60436(4) 0.67320(3) 1.44580(3) 0.05607(16) Uani 1 1 d . . . . .
I2 I 0.22358(4) 0.72853(4) 1.11066(3) 0.06076(16) Uani 1 1 d . . . . .
I3 I 0.27055(5) 1.10679(3) 1.35647(3) 0.06040(16) Uani 1 1 d . . . . .
N1 N 0.1165(7) 0.6440(6) 0.9473(5) 0.0726(16) Uani 1 1 d . . . . .
N2 N -0.1585(6) 0.6185(4) 0.6490(4) 0.0535(11) Uani 1 1 d . . . . .
N3 N -0.1932(6) 0.5541(4) 0.5782(4) 0.0521(11) Uani 1 1 d . . . . .
O1 O -0.0431(4) 0.4541(3) 0.6713(3) 0.0436(7) Uani 1 1 d . . . . .
O2 O -0.1388(5) 0.0814(4) 0.3974(4) 0.0608(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.372(7) . ?
C1 C2 1.397(8) . ?
C1 I1 2.078(5) . ?
C2 F1 1.342(6) . ?
C2 C3 1.381(8) . ?
C3 C4 1.395(8) . ?
C3 I2 2.092(5) . ?
C4 F2 1.338(6) . ?
C4 C5 1.371(8) . ?
C5 C6 1.380(8) . ?
C5 I3 2.093(5) . ?
C6 F3 1.332(6) . ?
C7 N1 1.321(10) . ?
C7 C8 1.362(10) . ?
C8 C9 1.397(9) . ?
C9 C10 1.381(9) . ?
C9 C12 1.462(8) . ?
C10 C11 1.390(11) . ?
C11 N1 1.311(11) . ?
C12 N2 1.282(8) . ?
C12 O1 1.364(6) . ?
C13 N3 1.301(7) . ?
C13 O1 1.370(7) . ?
C13 C14 1.436(7) . ?
C14 C15 1.393(8) . ?
C14 C19 1.400(7) . ?
C15 C16 1.372(8) . ?
C16 C17 1.388(8) . ?
C17 O2 1.358(7) . ?
C17 C18 1.391(9) . ?
C18 C19 1.380(8) . ?
C20 O2 1.432(8) . ?
C20 C21 1.514(8) . ?
C21 C22 1.528(10) . ?
C22 C23 1.523(10) . ?
C23 C24 1.525(11) . ?
C24 C25 1.505(10) . ?
C25 C26 1.507(11) . ?
C26 C27 1.520(11) . ?
C27 C28 1.526(14) . ?
N2 N3 1.394(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.0(5) . . ?
C6 C1 I1 121.2(4) . . ?
C2 C1 I1 122.9(4) . . ?
F1 C2 C3 118.2(5) . . ?
F1 C2 C1 118.2(5) . . ?
C3 C2 C1 123.6(5) . . ?
C2 C3 C4 116.9(5) . . ?
C2 C3 I2 121.1(4) . . ?
C4 C3 I2 122.0(4) . . ?
F2 C4 C5 119.8(5) . . ?
F2 C4 C3 118.3(5) . . ?
C5 C4 C3 121.9(5) . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 I3 121.7(4) . . ?
C6 C5 I3 120.1(4) . . ?
F3 C6 C1 118.1(5) . . ?
F3 C6 C5 118.5(5) . . ?
C1 C6 C5 123.4(5) . . ?
N1 C7 C8 124.1(7) . . ?
C7 C8 C9 119.1(7) . . ?
C10 C9 C8 117.8(6) . . ?
C10 C9 C12 122.5(6) . . ?
C8 C9 C12 119.7(5) . . ?
C9 C10 C11 117.2(7) . . ?
N1 C11 C10 125.3(7) . . ?
N2 C12 O1 112.9(5) . . ?
N2 C12 C9 128.3(5) . . ?
O1 C12 C9 118.9(5) . . ?
N3 C13 O1 111.2(5) . . ?
N3 C13 C14 128.9(5) . . ?
O1 C13 C14 119.9(5) . . ?
C15 C14 C19 118.2(5) . . ?
C15 C14 C13 119.8(5) . . ?
C19 C14 C13 121.9(5) . . ?
C16 C15 C14 121.8(5) . . ?
C15 C16 C17 119.3(6) . . ?
O2 C17 C16 123.8(5) . . ?
O2 C17 C18 116.0(5) . . ?
C16 C17 C18 120.2(5) . . ?
C19 C18 C17 120.0(5) . . ?
C18 C19 C14 120.5(5) . . ?
O2 C20 C21 108.1(6) . . ?
C20 C21 C22 110.0(6) . . ?
C23 C22 C21 113.3(7) . . ?
C22 C23 C24 113.1(7) . . ?
C25 C24 C23 114.4(7) . . ?
C24 C25 C26 113.7(7) . . ?
C25 C26 C27 114.3(7) . . ?
C26 C27 C28 113.9(8) . . ?
C11 N1 C7 116.4(6) . . ?
C12 N2 N3 106.3(4) . . ?
C13 N3 N2 107.0(5) . . ?
C12 O1 C13 102.6(4) . . ?
C17 O2 C20 118.3(5) . . ?

_refine_diff_density_max         1.212
_refine_diff_density_min         -2.009
_refine_diff_density_rms         0.169




####################################################################### 
# 
# 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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1409981'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 F3 I3 N3 O2'
_chemical_formula_weight         861.20

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.5563(3)
_cell_length_b                   11.4823(3)
_cell_length_c                   14.1520(4)
_cell_angle_alpha                99.118(2)
_cell_angle_beta                 92.177(2)
_cell_angle_gamma                92.289(2)
_cell_volume                     1530.48(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7649
_cell_measurement_theta_min      3.0970
_cell_measurement_theta_max      73.7680

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5989
_exptl_crystal_size_mid          0.1824
_exptl_crystal_size_min          0.1593
_exptl_absorpt_coefficient_mu    24.458
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.011
_exptl_absorpt_correction_T_max  0.188
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 5.2977
_diffrn_reflns_number            11481
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.166
_diffrn_reflns_theta_max         73.922
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6006
_reflns_number_gt                5482
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR-92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0492P)²+0.2280P] 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     SHELXL
_refine_ls_extinction_coef       0.00286(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6006
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.1940(4) -0.2963(3) 0.2211(2) 0.0502(7) Uani 1 1 d . . . . .
C2 C 0.2252(4) -0.4037(3) 0.2457(2) 0.0507(7) Uani 1 1 d . . . . .
C3 C 0.1670(4) -0.4474(3) 0.3210(2) 0.0464(7) Uani 1 1 d . . . . .
C4 C 0.0743(4) -0.3770(3) 0.3746(2) 0.0476(7) Uani 1 1 d . . . . .
C5 C 0.0372(4) -0.2685(3) 0.3533(2) 0.0476(7) Uani 1 1 d . . . . .
C6 C 0.0988(4) -0.2306(3) 0.2762(3) 0.0496(7) Uani 1 1 d . . . . .
C7 C 0.6432(7) 0.0529(6) 0.0918(4) 0.0925(18) Uani 1 1 d . . . . .
H7 H 0.7067 0.0050 0.0581 0.111 Uiso 1 1 calc R U . . .
C8 C 0.5867(6) 0.0150(4) 0.1724(4) 0.0748(12) Uani 1 1 d . . . . .
H8 H 0.6139 -0.0542 0.1927 0.090 Uiso 1 1 calc R U . . .
C9 C 0.4889(4) 0.0846(3) 0.2204(3) 0.0512(7) Uani 1 1 d . . . . .
C10 C 0.4548(5) 0.1879(4) 0.1862(3) 0.0691(11) Uani 1 1 d . . . . .
H10 H 0.3890 0.2370 0.2160 0.083 Uiso 1 1 calc R U . . .
C11 C 0.5206(6) 0.2154(5) 0.1076(4) 0.0779(13) Uani 1 1 d . . . . .
H11 H 0.4982 0.2851 0.0860 0.093 Uiso 1 1 calc R U . . .
C12 C 0.4202(4) 0.0538(3) 0.3039(3) 0.0494(7) Uani 1 1 d . . . . .
C13 C 0.3666(4) -0.0479(3) 0.4114(2) 0.0471(7) Uani 1 1 d . . . . .
C14 C 0.3669(4) -0.1447(3) 0.4651(2) 0.0475(7) Uani 1 1 d . . . . .
C15 C 0.4503(4) -0.2418(3) 0.4414(3) 0.0549(8) Uani 1 1 d . . . . .
H15 H 0.5091 -0.2443 0.3903 0.066 Uiso 1 1 calc R U . . .
C16 C 0.4458(5) -0.3332(3) 0.4930(3) 0.0589(9) Uani 1 1 d . . . . .
H16 H 0.5017 -0.3972 0.4767 0.071 Uiso 1 1 calc R U . . .
C17 C 0.3583(4) -0.3309(3) 0.5698(3) 0.0539(8) Uani 1 1 d . . . . .
C18 C 0.2743(4) -0.2355(4) 0.5934(3) 0.0575(8) Uani 1 1 d . . . . .
H18 H 0.2147 -0.2335 0.6440 0.069 Uiso 1 1 calc R U . . .
C19 C 0.2797(4) -0.1436(3) 0.5414(3) 0.0560(8) Uani 1 1 d . . . . .
H19 H 0.2238 -0.0796 0.5577 0.067 Uiso 1 1 calc R U . . .
C20 C 0.2731(5) -0.4260(4) 0.6961(3) 0.0633(9) Uani 1 1 d . . . . .
H20A H 0.1757 -0.4284 0.6735 0.076 Uiso 1 1 calc R U . . .
H20B H 0.2913 -0.3550 0.7428 0.076 Uiso 1 1 calc R U . . .
C21 C 0.3008(6) -0.5336(4) 0.7418(4) 0.0715(11) Uani 1 1 d . . . . .
H21A H 0.2777 -0.6043 0.6956 0.086 Uiso 1 1 calc R U . . .
H21B H 0.3996 -0.5333 0.7602 0.086 Uiso 1 1 calc R U . . .
C22 C 0.2155(6) -0.5355(4) 0.8284(4) 0.0737(12) Uani 1 1 d . . . . .
H22A H 0.1179 -0.5271 0.8105 0.088 Uiso 1 1 calc R U . . .
H22B H 0.2451 -0.4679 0.8762 0.088 Uiso 1 1 calc R U . . .
C23 C 0.2270(6) -0.6477(5) 0.8736(4) 0.0814(14) Uani 1 1 d . . . . .
H23A H 0.1957 -0.7155 0.8266 0.098 Uiso 1 1 calc R U . . .
H23B H 0.3246 -0.6570 0.8912 0.098 Uiso 1 1 calc R U . . .
C24 C 0.1409(7) -0.6452(5) 0.9617(4) 0.0832(14) Uani 1 1 d . . . . .
H24A H 0.0460 -0.6253 0.9461 0.100 Uiso 1 1 calc R U . . .
H24B H 0.1802 -0.5836 1.0117 0.100 Uiso 1 1 calc R U . . .
C25 C 0.1358(7) -0.7622(5) 1.0000(5) 0.0871(16) Uani 1 1 d . . . . .
H25A H 0.0936 -0.8233 0.9508 0.105 Uiso 1 1 calc R U . . .
H25B H 0.2309 -0.7835 1.0137 0.105 Uiso 1 1 calc R U . . .
C26 C 0.0537(9) -0.7581(7) 1.0898(5) 0.107(2) Uani 1 1 d . . . . .
H26A H -0.0424 -0.7403 1.0753 0.128 Uiso 1 1 calc R U . . .
H26B H 0.0934 -0.6947 1.1380 0.128 Uiso 1 1 calc R U . . .
C27 C 0.0538(11) -0.8726(8) 1.1305(6) 0.133(3) Uani 1 1 d . . . . .
H27A H 0.0000 -0.8649 1.1869 0.200 Uiso 1 1 calc R U . . .
H27B H 0.1484 -0.8898 1.1467 0.200 Uiso 1 1 calc R U . . .
H27C H 0.0130 -0.9357 1.0836 0.200 Uiso 1 1 calc R U . . .
N1 N 0.6133(5) 0.1499(4) 0.0609(3) 0.0807(11) Uani 1 1 d . . . . .
N2 N 0.3305(4) 0.1117(3) 0.3541(2) 0.0575(7) Uani 1 1 d . . . . .
N3 N 0.2956(4) 0.0456(3) 0.4253(2) 0.0565(7) Uani 1 1 d . . . . .
O1 O 0.4498(3) -0.0492(2) 0.33492(18) 0.0496(5) Uani 1 1 d . . . . .
O2 O 0.3625(4) -0.4243(3) 0.6174(2) 0.0676(7) Uani 1 1 d . . . . .
F1 F 0.3156(3) -0.4698(2) 0.19218(19) 0.0696(6) Uani 1 1 d . . . . .
F2 F 0.0180(3) -0.4161(2) 0.44853(18) 0.0660(6) Uani 1 1 d . . . . .
F3 F 0.0657(3) -0.1251(2) 0.2544(2) 0.0710(6) Uani 1 1 d . . . . .
I1 I 0.28114(3) -0.23305(3) 0.10423(2) 0.06336(11) Uani 1 1 d . . . . .
I2 I 0.21556(3) -0.61039(2) 0.35712(2) 0.06538(11) Uani 1 1 d . . . . .
I3 I -0.10278(3) -0.16906(2) 0.43843(2) 0.05760(10) 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 1.374(5) . ?
C1 C6 1.389(5) . ?
C1 I1 2.096(3) . ?
C2 F1 1.348(4) . ?
C2 C3 1.374(5) . ?
C3 C4 1.389(5) . ?
C3 I2 2.081(3) . ?
C4 F2 1.325(4) . ?
C4 C5 1.384(5) . ?
C5 C6 1.379(5) . ?
C5 I3 2.087(3) . ?
C6 F3 1.343(4) . ?
C7 N1 1.298(8) . ?
C7 C8 1.402(7) . ?
C8 C9 1.382(6) . ?
C9 C10 1.396(6) . ?
C9 C12 1.457(5) . ?
C10 C11 1.371(7) . ?
C11 N1 1.314(7) . ?
C12 N2 1.275(5) . ?
C12 O1 1.362(4) . ?
C13 N3 1.285(5) . ?
C13 O1 1.365(4) . ?
C13 C14 1.443(5) . ?
C14 C19 1.388(5) . ?
C14 C15 1.401(5) . ?
C15 C16 1.371(6) . ?
C16 C17 1.393(6) . ?
C17 O2 1.355(5) . ?
C17 C18 1.390(6) . ?
C18 C19 1.379(5) . ?
C20 O2 1.432(6) . ?
C20 C21 1.510(6) . ?
C21 C22 1.500(8) . ?
C22 C23 1.532(6) . ?
C23 C24 1.518(9) . ?
C24 C25 1.526(7) . ?
C25 C26 1.515(10) . ?
C26 C27 1.516(10) . ?
N2 N3 1.396(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.1(3) . . ?
C2 C1 I1 122.5(3) . . ?
C6 C1 I1 120.4(3) . . ?
F1 C2 C3 118.7(3) . . ?
F1 C2 C1 118.0(3) . . ?
C3 C2 C1 123.2(3) . . ?
C2 C3 C4 117.1(3) . . ?
C2 C3 I2 122.6(3) . . ?
C4 C3 I2 120.2(2) . . ?
F2 C4 C5 118.8(3) . . ?
F2 C4 C3 118.5(3) . . ?
C5 C4 C3 122.6(3) . . ?
C6 C5 C4 117.0(3) . . ?
C6 C5 I3 123.2(3) . . ?
C4 C5 I3 119.7(2) . . ?
F3 C6 C5 118.3(3) . . ?
F3 C6 C1 118.9(3) . . ?
C5 C6 C1 122.8(3) . . ?
N1 C7 C8 124.8(5) . . ?
C9 C8 C7 117.3(5) . . ?
C8 C9 C10 117.9(4) . . ?
C8 C9 C12 122.7(4) . . ?
C10 C9 C12 119.4(4) . . ?
C11 C10 C9 118.5(4) . . ?
N1 C11 C10 124.3(5) . . ?
N2 C12 O1 112.7(3) . . ?
N2 C12 C9 128.1(3) . . ?
O1 C12 C9 119.2(3) . . ?
N3 C13 O1 111.8(3) . . ?
N3 C13 C14 128.4(3) . . ?
O1 C13 C14 119.8(3) . . ?
C19 C14 C15 118.5(3) . . ?
C19 C14 C13 119.3(3) . . ?
C15 C14 C13 122.1(3) . . ?
C16 C15 C14 120.5(4) . . ?
C15 C16 C17 120.5(4) . . ?
O2 C17 C18 124.2(4) . . ?
O2 C17 C16 116.3(3) . . ?
C18 C17 C16 119.5(4) . . ?
C19 C18 C17 119.7(4) . . ?
C18 C19 C14 121.3(4) . . ?
O2 C20 C21 109.1(4) . . ?
C22 C21 C20 111.1(4) . . ?
C21 C22 C23 114.4(5) . . ?
C24 C23 C22 112.6(5) . . ?
C23 C24 C25 113.3(5) . . ?
C26 C25 C24 113.1(6) . . ?
C25 C26 C27 113.2(8) . . ?
C7 N1 C11 117.1(4) . . ?
C12 N2 N3 106.4(3) . . ?
C13 N3 N2 106.7(3) . . ?
C12 O1 C13 102.3(3) . . ?
C17 O2 C20 118.0(3) . . ?

_refine_diff_density_max         1.049
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.136



####################################################################### 
# 
# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 1409982'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H46 F6 I6 N6 O4'
_chemical_formula_weight         1694.35

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.0662(2)
_cell_length_b                   14.4987(3)
_cell_length_c                   20.6364(5)
_cell_angle_alpha                82.220(2)
_cell_angle_beta                 81.567(2)
_cell_angle_gamma                89.177(2)
_cell_volume                     2951.78(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11336
_cell_measurement_theta_min      3.9580
_cell_measurement_theta_max      73.4980

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4500
_exptl_crystal_size_mid          0.2197
_exptl_crystal_size_min          0.2000
_exptl_absorpt_coefficient_mu    25.351
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.056
_exptl_absorpt_correction_T_max  0.393
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 5.2977
_diffrn_reflns_number            22644
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.076
_diffrn_reflns_theta_max         73.808
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11582
_reflns_number_gt                9443
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1016P)²+2.9452P] 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     SHELXL
_refine_ls_extinction_coef       0.00029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11582
_refine_ls_number_parameters     668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1536
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.7205(7) 0.1586(4) 0.6154(4) 0.0438(14) Uani 1 1 d . . . . .
C2 C 0.6262(6) 0.2099(4) 0.5833(3) 0.0400(13) Uani 1 1 d . . . . .
C3 C 0.5739(6) 0.2919(4) 0.6038(3) 0.0362(12) Uani 1 1 d . . . . .
C4 C 0.6178(6) 0.3211(4) 0.6575(3) 0.0377(12) Uani 1 1 d . . . . .
C5 C 0.7100(6) 0.2711(4) 0.6912(3) 0.0386(12) Uani 1 1 d . . . . .
C6 C 0.7604(7) 0.1919(4) 0.6686(3) 0.0440(14) Uani 1 1 d . . . . .
C7 C 0.6661(6) 0.2583(4) 0.1639(3) 0.0400(13) Uani 1 1 d . . . . .
C8 C 0.5695(6) 0.3091(4) 0.1328(3) 0.0386(12) Uani 1 1 d . . . . .
C9 C 0.5112(6) 0.3871(4) 0.1557(3) 0.0386(12) Uani 1 1 d . . . . .
C10 C 0.5524(6) 0.4143(4) 0.2109(3) 0.0409(13) Uani 1 1 d . . . . .
C11 C 0.6454(6) 0.3650(4) 0.2436(3) 0.0408(13) Uani 1 1 d . . . . .
C12 C 0.7027(6) 0.2885(4) 0.2184(3) 0.0398(13) Uani 1 1 d . . . . .
C13 C -0.1290(8) 0.8209(6) 0.4934(5) 0.063(2) Uani 1 1 d . . . . .
H13 H -0.1958 0.8460 0.4696 0.075 Uiso 1 1 calc R U . . .
C14 C -0.0648(8) 0.7423(6) 0.4745(4) 0.0578(18) Uani 1 1 d . . . . .
H14 H -0.0904 0.7140 0.4403 0.069 Uiso 1 1 calc R U . . .
C15 C 0.0393(6) 0.7059(4) 0.5075(3) 0.0378(12) Uani 1 1 d . . . . .
C16 C 0.0687(7) 0.7512(5) 0.5583(4) 0.0532(17) Uani 1 1 d . . . . .
H16 H 0.1372 0.7292 0.5819 0.064 Uiso 1 1 calc R U . . .
C17 C -0.0024(9) 0.8285(5) 0.5742(4) 0.0586(19) Uani 1 1 d . . . . .
H17 H 0.0205 0.8579 0.6084 0.070 Uiso 1 1 calc R U . . .
C18 C 0.1119(6) 0.6221(4) 0.4919(3) 0.0384(12) Uani 1 1 d . . . . .
C19 C 0.1743(5) 0.5090(4) 0.4392(3) 0.0369(12) Uani 1 1 d . . . . .
C20 C 0.1819(6) 0.4492(4) 0.3884(3) 0.0396(13) Uani 1 1 d . . . . .
C21 C 0.0885(7) 0.4530(5) 0.3441(3) 0.0477(15) Uani 1 1 d . . . . .
H21 H 0.0218 0.4981 0.3452 0.057 Uiso 1 1 calc R U . . .
C22 C 0.0940(8) 0.3913(6) 0.2995(4) 0.0545(17) Uani 1 1 d . . . . .
H22 H 0.0301 0.3937 0.2711 0.065 Uiso 1 1 calc R U . . .
C23 C 0.1955(8) 0.3244(6) 0.2964(4) 0.0542(17) Uani 1 1 d . . . . .
C24 C 0.2894(7) 0.3198(6) 0.3397(4) 0.0547(17) Uani 1 1 d . . . . .
H24 H 0.3562 0.2748 0.3383 0.066 Uiso 1 1 calc R U . . .
C25 C 0.2832(7) 0.3817(5) 0.3847(4) 0.0502(16) Uani 1 1 d . . . . .
H25 H 0.3471 0.3790 0.4131 0.060 Uiso 1 1 calc R U . . .
C29 C 0.2804(9) 0.1910(7) 0.2500(5) 0.067(2) Uani 1 1 d . . . . .
H29A H 0.2642 0.1498 0.2915 0.080 Uiso 1 1 calc R U . . .
H29B H 0.3722 0.2137 0.2437 0.080 Uiso 1 1 calc R U . . .
C30 C 0.2579(11) 0.1386(9) 0.1926(6) 0.084(3) Uani 1 1 d . . . . .
H30A H 0.1652 0.1178 0.1985 0.101 Uiso 1 1 calc R U . . .
H30B H 0.2754 0.1800 0.1512 0.101 Uiso 1 1 calc R U . . .
C31 C 0.3509(11) 0.0553(7) 0.1903(5) 0.074(2) Uani 1 1 d . . . . .
H31A H 0.4420 0.0757 0.1908 0.089 Uiso 1 1 calc R U . . .
H31B H 0.3254 0.0109 0.2296 0.089 Uiso 1 1 calc R U . . .
C32 C 0.3473(11) 0.0082(9) 0.1306(5) 0.083(3) Uani 1 1 d . . . . .
H32A H 0.3734 0.0531 0.0916 0.099 Uiso 1 1 calc R U . . .
H32B H 0.2554 -0.0106 0.1300 0.099 Uiso 1 1 calc R U . . .
C33 C 0.4368(11) -0.0768(8) 0.1259(6) 0.082(3) Uani 1 1 d . . . . .
H33A H 0.5288 -0.0573 0.1252 0.098 Uiso 1 1 calc R U . . .
H33B H 0.4126 -0.1204 0.1658 0.098 Uiso 1 1 calc R U . . .
C34 C 0.4320(13) -0.1266(10) 0.0683(7) 0.101(4) Uani 1 1 d . . . . .
H34A H 0.4584 -0.0837 0.0283 0.121 Uiso 1 1 calc R U . . .
H34B H 0.3399 -0.1454 0.0683 0.121 Uiso 1 1 calc R U . . .
C35 C 0.5198(13) -0.2115(10) 0.0660(8) 0.113(5) Uani 1 1 d . . . . .
H35A H 0.5103 -0.2396 0.0274 0.169 Uiso 1 1 calc R U . . .
H35B H 0.4933 -0.2553 0.1049 0.169 Uiso 1 1 calc R U . . .
H35C H 0.6118 -0.1936 0.0644 0.169 Uiso 1 1 calc R U . . .
C36 C 1.0408(9) 0.0703(5) -0.1178(5) 0.063(2) Uani 1 1 d . . . . .
H36 H 1.0237 0.0427 -0.1539 0.075 Uiso 1 1 calc R U . . .
C37 C 0.9714(8) 0.1490(5) -0.1050(4) 0.0541(17) Uani 1 1 d . . . . .
H37 H 0.9080 0.1732 -0.1311 0.065 Uiso 1 1 calc R U . . .
C38 C 0.9982(6) 0.1922(4) -0.0516(3) 0.0379(12) Uani 1 1 d . . . . .
C39 C 1.0912(8) 0.1518(6) -0.0144(4) 0.0568(18) Uani 1 1 d . . . . .
H39 H 1.1115 0.1775 0.0219 0.068 Uiso 1 1 calc R U . . .
C40 C 1.1549(9) 0.0705(6) -0.0327(5) 0.065(2) Uani 1 1 d . . . . .
H40 H 1.2183 0.0435 -0.0075 0.078 Uiso 1 1 calc R U . . .
C41 C 0.9255(6) 0.2766(4) -0.0363(3) 0.0361(12) Uani 1 1 d . . . . .
C42 C 0.8662(6) 0.3914(4) 0.0150(3) 0.0340(11) Uani 1 1 d . . . . .
C43 C 0.8667(6) 0.4543(4) 0.0639(3) 0.0384(12) Uani 1 1 d . . . . .
C44 C 0.7686(7) 0.5231(5) 0.0669(4) 0.0464(14) Uani 1 1 d . . . . .
H44 H 0.7057 0.5272 0.0378 0.056 Uiso 1 1 calc R U . . .
C45 C 0.7634(7) 0.5860(5) 0.1128(4) 0.0517(16) Uani 1 1 d . . . . .
H45 H 0.6976 0.6317 0.1147 0.062 Uiso 1 1 calc R U . . .
C46 C 0.8585(7) 0.5789(5) 0.1557(3) 0.0486(15) Uani 1 1 d . . . . .
C47 C 0.9583(8) 0.5114(5) 0.1508(4) 0.0515(16) Uani 1 1 d . . . . .
H47 H 1.0246 0.5091 0.1780 0.062 Uiso 1 1 calc R U . . .
C48 C 0.9604(7) 0.4493(5) 0.1073(4) 0.0472(14) Uani 1 1 d . . . . .
H48 H 1.0251 0.4029 0.1065 0.057 Uiso 1 1 calc R U . . .
C49 C 0.7628(9) 0.7047(6) 0.2098(4) 0.061(2) Uani 1 1 d . . . . .
H49A H 0.6751 0.6751 0.2217 0.073 Uiso 1 1 calc R U . . .
H49B H 0.7629 0.7459 0.1686 0.073 Uiso 1 1 calc R U . . .
C50 C 0.7903(11) 0.7593(7) 0.2630(5) 0.074(3) Uani 1 1 d . . . . .
H50A H 0.8826 0.7813 0.2537 0.088 Uiso 1 1 calc R U . . .
H50B H 0.7795 0.7189 0.3050 0.088 Uiso 1 1 calc R U . . .
C51 C 0.6964(10) 0.8427(6) 0.2687(4) 0.066(2) Uani 1 1 d . . . . .
H51A H 0.7085 0.8831 0.2268 0.079 Uiso 1 1 calc R U . . .
H51B H 0.6043 0.8204 0.2768 0.079 Uiso 1 1 calc R U . . .
C52 C 0.7181(12) 0.8993(7) 0.3227(5) 0.080(3) Uani 1 1 d . . . . .
H52A H 0.7023 0.8595 0.3648 0.096 Uiso 1 1 calc R U . . .
H52B H 0.8113 0.9193 0.3156 0.096 Uiso 1 1 calc R U . . .
C53 C 0.6311(11) 0.9825(7) 0.3265(5) 0.073(2) Uani 1 1 d . . . . .
H53A H 0.5382 0.9620 0.3348 0.088 Uiso 1 1 calc R U . . .
H53B H 0.6450 1.0210 0.2838 0.088 Uiso 1 1 calc R U . . .
C54 C 0.6529(19) 1.0419(11) 0.3783(7) 0.122(5) Uani 1 1 d . . . . .
H54A H 0.7452 1.0640 0.3697 0.146 Uiso 1 1 calc R U . . .
H54B H 0.6404 1.0036 0.4211 0.146 Uiso 1 1 calc R U . . .
C55 C 0.5608(17) 1.1247(9) 0.3814(8) 0.119(5) Uani 1 1 d . . . . .
H55A H 0.5804 1.1592 0.4155 0.178 Uiso 1 1 calc R U . . .
H55B H 0.4691 1.1036 0.3911 0.178 Uiso 1 1 calc R U . . .
H55C H 0.5742 1.1641 0.3397 0.178 Uiso 1 1 calc R U . . .
F1 F 0.5854(5) 0.1802(3) 0.5310(2) 0.0662(12) Uani 1 1 d . . . . .
F2 F 0.5671(5) 0.3992(3) 0.6783(2) 0.0571(10) Uani 1 1 d . . . . .
F3 F 0.8521(5) 0.1422(3) 0.6995(3) 0.0653(12) Uani 1 1 d . . . . .
F4 F 0.5321(5) 0.2811(3) 0.0790(2) 0.0616(11) Uani 1 1 d . . . . .
F5 F 0.4979(5) 0.4910(3) 0.2330(2) 0.0599(11) Uani 1 1 d . . . . .
F6 F 0.7963(4) 0.2417(3) 0.2493(2) 0.0600(11) Uani 1 1 d . . . . .
I1 I 0.79408(5) 0.03341(3) 0.58310(2) 0.05245(15) Uani 1 1 d . . . . .
I2 I 0.43278(4) 0.37082(3) 0.55482(2) 0.04732(14) Uani 1 1 d . . . . .
I3 I 0.76866(7) 0.31793(4) 0.77446(3) 0.07152(19) Uani 1 1 d . . . . .
I4 I 0.75169(4) 0.13891(3) 0.12691(2) 0.04890(14) Uani 1 1 d . . . . .
I5 I 0.37738(5) 0.47002(4) 0.10439(2) 0.05333(15) Uani 1 1 d . . . . .
I6 I 0.69588(5) 0.40799(4) 0.33023(3) 0.05685(15) Uani 1 1 d . . . . .
N1 N -0.1022(7) 0.8633(4) 0.5431(3) 0.0572(15) Uani 1 1 d . . . . .
N2 N 0.1941(6) 0.5750(4) 0.5252(3) 0.0485(13) Uani 1 1 d . . . . .
N3 N 0.2355(6) 0.5005(4) 0.4915(3) 0.0479(13) Uani 1 1 d . . . . .
N4 N 1.1311(7) 0.0305(4) -0.0823(4) 0.0580(16) Uani 1 1 d . . . . .
N5 N 0.8322(6) 0.3168(4) -0.0653(3) 0.0485(13) Uani 1 1 d . . . . .
N6 N 0.7929(6) 0.3923(4) -0.0311(3) 0.0503(14) Uani 1 1 d . . . . .
O1 O 0.0922(4) 0.5853(3) 0.4372(2) 0.0397(9) Uani 1 1 d . . . . .
O2 O 0.1909(7) 0.2655(5) 0.2508(3) 0.0751(17) Uani 1 1 d . . . . .
O3 O 0.9554(4) 0.3192(3) 0.0143(2) 0.0379(9) Uani 1 1 d . . . . .
O4 O 0.8632(6) 0.6362(4) 0.2016(3) 0.0649(14) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.369(10) . ?
C1 C2 1.388(9) . ?
C1 I1 2.105(6) . ?
C2 F1 1.334(8) . ?
C2 C3 1.386(8) . ?
C3 C4 1.371(9) . ?
C3 I2 2.099(5) . ?
C4 F2 1.332(7) . ?
C4 C5 1.380(8) . ?
C5 C6 1.363(9) . ?
C5 I3 2.094(6) . ?
C6 F3 1.344(7) . ?
C7 C12 1.361(10) . ?
C7 C8 1.391(9) . ?
C7 I4 2.108(6) . ?
C8 F4 1.337(8) . ?
C8 C9 1.376(8) . ?
C9 C10 1.375(9) . ?
C9 I5 2.099(6) . ?
C10 F5 1.338(7) . ?
C10 C11 1.370(9) . ?
C11 C12 1.372(9) . ?
C11 I6 2.103(6) . ?
C12 F6 1.341(7) . ?
C13 N1 1.327(12) . ?
C13 C14 1.377(11) . ?
C14 C15 1.391(9) . ?
C15 C16 1.378(11) . ?
C15 C18 1.459(8) . ?
C16 C17 1.373(10) . ?
C17 N1 1.328(11) . ?
C18 N2 1.283(8) . ?
C18 O1 1.353(8) . ?
C19 N3 1.310(9) . ?
C19 O1 1.371(7) . ?
C19 C20 1.441(10) . ?
C20 C21 1.399(10) . ?
C20 C25 1.404(9) . ?
C21 C22 1.362(11) . ?
C22 C23 1.399(11) . ?
C23 O2 1.359(10) . ?
C23 C24 1.389(11) . ?
C24 C25 1.370(11) . ?
C29 O2 1.397(11) . ?
C29 C30 1.534(13) . ?
C30 C31 1.519(15) . ?
C31 C32 1.493(13) . ?
C32 C33 1.521(16) . ?
C33 C34 1.480(16) . ?
C34 C35 1.507(17) . ?
C36 N4 1.327(11) . ?
C36 C37 1.365(10) . ?
C37 C38 1.400(10) . ?
C38 C39 1.370(10) . ?
C38 C41 1.464(8) . ?
C39 C40 1.404(11) . ?
C40 N4 1.295(12) . ?
C41 N5 1.279(8) . ?
C41 O3 1.354(8) . ?
C42 N6 1.285(9) . ?
C42 O3 1.369(7) . ?
C42 C43 1.450(9) . ?
C43 C48 1.388(10) . ?
C43 C44 1.394(9) . ?
C44 C45 1.397(10) . ?
C45 C46 1.390(11) . ?
C46 O4 1.348(9) . ?
C46 C47 1.394(11) . ?
C47 C48 1.353(10) . ?
C49 O4 1.415(10) . ?
C49 C50 1.498(12) . ?
C50 C51 1.531(14) . ?
C51 C52 1.512(12) . ?
C52 C53 1.485(14) . ?
C53 C54 1.502(15) . ?
C54 C55 1.510(19) . ?
N2 N3 1.390(8) . ?
N5 N6 1.403(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.5(6) . . ?
C6 C1 I1 122.5(5) . . ?
C2 C1 I1 120.0(5) . . ?
F1 C2 C3 119.0(5) . . ?
F1 C2 C1 119.3(6) . . ?
C3 C2 C1 121.7(6) . . ?
C4 C3 C2 117.8(5) . . ?
C4 C3 I2 120.2(4) . . ?
C2 C3 I2 122.0(5) . . ?
F2 C4 C3 118.5(5) . . ?
F2 C4 C5 119.4(6) . . ?
C3 C4 C5 122.0(6) . . ?
C6 C5 C4 118.0(6) . . ?
C6 C5 I3 122.0(5) . . ?
C4 C5 I3 120.0(5) . . ?
F3 C6 C5 119.7(6) . . ?
F3 C6 C1 117.4(6) . . ?
C5 C6 C1 122.9(6) . . ?
C12 C7 C8 117.7(5) . . ?
C12 C7 I4 121.8(5) . . ?
C8 C7 I4 120.5(5) . . ?
F4 C8 C9 119.0(6) . . ?
F4 C8 C7 118.9(6) . . ?
C9 C8 C7 122.1(6) . . ?
C10 C9 C8 117.5(5) . . ?
C10 C9 I5 120.2(4) . . ?
C8 C9 I5 122.0(5) . . ?
F5 C10 C11 120.0(6) . . ?
F5 C10 C9 118.0(6) . . ?
C11 C10 C9 122.0(6) . . ?
C10 C11 C12 118.5(6) . . ?
C10 C11 I6 119.5(5) . . ?
C12 C11 I6 122.0(4) . . ?
F6 C12 C7 119.4(6) . . ?
F6 C12 C11 118.5(6) . . ?
C7 C12 C11 122.1(6) . . ?
N1 C13 C14 124.5(7) . . ?
C13 C14 C15 118.6(8) . . ?
C16 C15 C14 116.8(6) . . ?
C16 C15 C18 120.5(6) . . ?
C14 C15 C18 122.7(7) . . ?
C17 C16 C15 120.5(7) . . ?
N1 C17 C16 123.1(8) . . ?
N2 C18 O1 113.1(6) . . ?
N2 C18 C15 127.7(6) . . ?
O1 C18 C15 119.2(5) . . ?
N3 C19 O1 111.2(6) . . ?
N3 C19 C20 128.6(5) . . ?
O1 C19 C20 120.2(5) . . ?
C21 C20 C25 118.4(7) . . ?
C21 C20 C19 122.5(5) . . ?
C25 C20 C19 119.1(6) . . ?
C22 C21 C20 120.7(6) . . ?
C21 C22 C23 120.3(7) . . ?
O2 C23 C24 124.5(8) . . ?
O2 C23 C22 115.6(7) . . ?
C24 C23 C22 119.8(7) . . ?
C25 C24 C23 119.7(7) . . ?
C24 C25 C20 121.1(7) . . ?
O2 C29 C30 107.6(9) . . ?
C31 C30 C29 109.9(9) . . ?
C32 C31 C30 112.8(10) . . ?
C31 C32 C33 115.4(10) . . ?
C34 C33 C32 116.5(11) . . ?
C33 C34 C35 115.0(12) . . ?
N4 C36 C37 124.5(8) . . ?
C36 C37 C38 118.3(7) . . ?
C39 C38 C37 117.9(6) . . ?
C39 C38 C41 122.4(6) . . ?
C37 C38 C41 119.8(6) . . ?
C38 C39 C40 118.1(8) . . ?
N4 C40 C39 124.3(8) . . ?
N5 C41 O3 113.5(5) . . ?
N5 C41 C38 127.4(6) . . ?
O3 C41 C38 119.1(5) . . ?
N6 C42 O3 111.4(5) . . ?
N6 C42 C43 129.5(5) . . ?
O3 C42 C43 119.1(5) . . ?
C48 C43 C44 118.9(6) . . ?
C48 C43 C42 123.0(6) . . ?
C44 C43 C42 118.1(6) . . ?
C43 C44 C45 121.0(7) . . ?
C46 C45 C44 118.6(7) . . ?
O4 C46 C45 123.5(7) . . ?
O4 C46 C47 116.8(7) . . ?
C45 C46 C47 119.7(7) . . ?
C48 C47 C46 121.2(7) . . ?
C47 C48 C43 120.5(6) . . ?
O4 C49 C50 109.1(8) . . ?
C49 C50 C51 112.1(9) . . ?
C52 C51 C50 114.3(9) . . ?
C53 C52 C51 114.5(9) . . ?
C52 C53 C54 115.9(10) . . ?
C53 C54 C55 114.2(13) . . ?
C13 N1 C17 116.5(7) . . ?
C18 N2 N3 106.6(6) . . ?
C19 N3 N2 106.4(5) . . ?
C40 N4 C36 117.0(7) . . ?
C41 N5 N6 105.3(5) . . ?
C42 N6 N5 107.3(5) . . ?
C18 O1 C19 102.6(5) . . ?
C23 O2 C29 118.4(7) . . ?
C41 O3 C42 102.5(5) . . ?
C46 O4 C49 119.3(7) . . ?

_refine_diff_density_max         1.675
_refine_diff_density_min         -2.606
_refine_diff_density_rms         0.183



####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1409983'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 F3 I3 N3 O2'
_chemical_formula_weight         833.15

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.0898(5)
_cell_length_b                   12.7927(8)
_cell_length_c                   13.8531(7)
_cell_angle_alpha                114.273(6)
_cell_angle_beta                 98.513(5)
_cell_angle_gamma                100.445(5)
_cell_volume                     1398.93(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6104
_cell_measurement_theta_min      3.5190
_cell_measurement_theta_max      73.1000

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5390
_exptl_crystal_size_mid          0.3859
_exptl_crystal_size_min          0.1508
_exptl_absorpt_coefficient_mu    26.732
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.012
_exptl_absorpt_correction_T_max  0.651
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            12194
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.613
_diffrn_reflns_theta_max         73.064
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5430
_reflns_number_gt                4405
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5430
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.2568
_refine_ls_wR_factor_gt          0.2240
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.7694(9) 0.2230(8) 0.2958(7) 0.0490(18) Uani 1 1 d . . . . .
C2 C 0.7167(10) 0.2856(8) 0.3860(8) 0.0502(18) Uani 1 1 d . . . . .
C3 C 0.6362(10) 0.2330(8) 0.4365(7) 0.0489(17) Uani 1 1 d . . . . .
C4 C 0.6095(9) 0.1136(8) 0.3981(7) 0.0471(17) Uani 1 1 d . . . . .
C5 C 0.6569(9) 0.0442(7) 0.3088(7) 0.0475(17) Uani 1 1 d . . . . .
C6 C 0.7374(10) 0.1006(8) 0.2597(7) 0.0486(17) Uani 1 1 d . . . . .
C7 C 0.8624(13) 0.4713(12) -0.1293(9) 0.068(3) Uani 1 1 d . . . . .
H7 H 0.8808 0.4103 -0.1880 0.081 Uiso 1 1 calc R U . . .
C8 C 0.7759(11) 0.4409(9) -0.0656(8) 0.056(2) Uani 1 1 d . . . . .
H8 H 0.7412 0.3618 -0.0797 0.067 Uiso 1 1 calc R U . . .
C9 C 0.7424(9) 0.5306(8) 0.0193(7) 0.0467(17) Uani 1 1 d . . . . .
C10 C 0.8003(12) 0.6476(9) 0.0386(8) 0.057(2) Uani 1 1 d . . . . .
H10 H 0.7818 0.7103 0.0958 0.068 Uiso 1 1 calc R U . . .
C11 C 0.8855(12) 0.6683(10) -0.0291(9) 0.060(2) Uani 1 1 d . . . . .
H11 H 0.9212 0.7465 -0.0172 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6498(9) 0.5051(8) 0.0893(6) 0.0440(16) Uani 1 1 d . . . . .
C13 C 0.5209(9) 0.4044(8) 0.1525(7) 0.0467(17) Uani 1 1 d . . . . .
C14 C 0.4458(10) 0.2992(9) 0.1614(7) 0.0506(19) Uani 1 1 d . . . . .
C15 C 0.4426(12) 0.1846(8) 0.0853(8) 0.056(2) Uani 1 1 d . . . . .
H15 H 0.4857 0.1747 0.0264 0.068 Uiso 1 1 calc R U . . .
C16 C 0.3753(14) 0.0854(9) 0.0976(9) 0.063(2) Uani 1 1 d . . . . .
H16 H 0.3752 0.0094 0.0484 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3080(11) 0.1026(9) 0.1850(8) 0.058(2) Uani 1 1 d . . . . .
C18 C 0.3060(12) 0.2173(9) 0.2603(8) 0.057(2) Uani 1 1 d . . . . .
H18 H 0.2589 0.2273 0.3175 0.069 Uiso 1 1 calc R U . . .
C19 C 0.3751(12) 0.3137(9) 0.2470(8) 0.057(2) Uani 1 1 d . . . . .
H19 H 0.3746 0.3897 0.2959 0.069 Uiso 1 1 calc R U . . .
C20 C 0.1836(12) 0.0123(9) 0.2836(8) 0.058(2) Uani 1 1 d . . . . .
H20A H 0.0916 0.0399 0.2779 0.070 Uiso 1 1 calc R U . . .
H20B H 0.2575 0.0696 0.3515 0.070 Uiso 1 1 calc R U . . .
C21 C 0.1436(13) -0.1096(10) 0.2815(9) 0.062(2) Uani 1 1 d . . . . .
H21A H 0.0698 -0.1660 0.2132 0.075 Uiso 1 1 calc R U . . .
H21B H 0.2360 -0.1371 0.2853 0.075 Uiso 1 1 calc R U . . .
C22 C 0.0755(11) -0.1050(10) 0.3766(8) 0.057(2) Uani 1 1 d . . . . .
H22A H -0.0091 -0.0683 0.3774 0.069 Uiso 1 1 calc R U . . .
H22B H 0.1538 -0.0550 0.4444 0.069 Uiso 1 1 calc R U . . .
C23 C 0.0163(11) -0.2264(9) 0.3723(8) 0.055(2) Uani 1 1 d . . . . .
H23A H -0.0605 -0.2768 0.3038 0.066 Uiso 1 1 calc R U . . .
H23B H 0.1014 -0.2625 0.3725 0.066 Uiso 1 1 calc R U . . .
C24 C -0.0540(13) -0.2240(10) 0.4646(9) 0.063(2) Uani 1 1 d . . . . .
H24A H -0.1400 -0.1889 0.4641 0.076 Uiso 1 1 calc R U . . .
H24B H 0.0223 -0.1736 0.5333 0.076 Uiso 1 1 calc R U . . .
C25 C -0.1104(15) -0.3457(11) 0.4582(10) 0.070(3) Uani 1 1 d . . . . .
H25A H -0.1544 -0.3385 0.5188 0.105 Uiso 1 1 calc R U . . .
H25B H -0.0254 -0.3801 0.4608 0.105 Uiso 1 1 calc R U . . .
H25C H -0.1874 -0.3958 0.3910 0.105 Uiso 1 1 calc R U . . .
F1 F 0.7445(9) 0.4044(5) 0.4221(6) 0.0725(17) Uani 1 1 d . . . . .
F2 F 0.5303(8) 0.0584(5) 0.4466(5) 0.0655(14) Uani 1 1 d . . . . .
F3 F 0.7878(9) 0.0362(6) 0.1733(5) 0.0703(15) Uani 1 1 d . . . . .
I1 I 0.89782(7) 0.30918(6) 0.22244(5) 0.0594(3) Uani 1 1 d . . . . .
I2 I 0.56281(8) 0.33423(6) 0.57438(5) 0.0621(3) Uani 1 1 d . . . . .
I3 I 0.61506(8) -0.14042(5) 0.25410(6) 0.0630(3) Uani 1 1 d . . . . .
N1 N 0.9203(10) 0.5826(9) -0.1111(7) 0.064(2) Uani 1 1 d . . . . .
N2 N 0.6170(9) 0.5821(7) 0.1732(6) 0.0529(16) Uani 1 1 d . . . . .
N3 N 0.5298(9) 0.5158(7) 0.2139(6) 0.0515(16) Uani 1 1 d . . . . .
O1 O 0.5955(7) 0.3920(5) 0.0718(5) 0.0485(12) Uani 1 1 d . . . . .
O2 O 0.2484(11) 0.0001(7) 0.1926(6) 0.0702(19) 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 1.388(13) . ?
C1 C6 1.391(13) . ?
C1 I1 2.101(8) . ?
C2 F1 1.350(11) . ?
C2 C3 1.356(12) . ?
C3 C4 1.354(13) . ?
C3 I2 2.104(8) . ?
C4 F2 1.349(10) . ?
C4 C5 1.378(13) . ?
C5 C6 1.371(13) . ?
C5 I3 2.101(8) . ?
C6 F3 1.345(10) . ?
C7 N1 1.328(16) . ?
C7 C8 1.386(14) . ?
C8 C9 1.384(14) . ?
C9 C10 1.390(13) . ?
C9 C12 1.469(12) . ?
C10 C11 1.376(13) . ?
C11 N1 1.343(15) . ?
C12 N2 1.295(12) . ?
C12 O1 1.346(11) . ?
C13 N3 1.304(12) . ?
C13 O1 1.361(10) . ?
C13 C14 1.457(13) . ?
C14 C19 1.394(13) . ?
C14 C15 1.402(14) . ?
C15 C16 1.393(13) . ?
C16 C17 1.392(15) . ?
C17 O2 1.377(12) . ?
C17 C18 1.414(15) . ?
C18 C19 1.374(14) . ?
C20 O2 1.432(12) . ?
C20 C21 1.523(14) . ?
C21 C22 1.521(13) . ?
C22 C23 1.522(14) . ?
C23 C24 1.504(14) . ?
C24 C25 1.509(15) . ?
N2 N3 1.395(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 C6 116.0(7) . . ?
C2 C1 I1 121.8(7) . . ?
C6 C1 I1 122.1(6) . . ?
F1 C2 C3 119.3(8) . . ?
F1 C2 C1 117.4(8) . . ?
C3 C2 C1 123.3(8) . . ?
C4 C3 C2 118.0(8) . . ?
C4 C3 I2 120.8(6) . . ?
C2 C3 I2 121.1(7) . . ?
F2 C4 C3 119.6(8) . . ?
F2 C4 C5 117.7(8) . . ?
C3 C4 C5 122.7(8) . . ?
C6 C5 C4 117.5(8) . . ?
C6 C5 I3 121.3(7) . . ?
C4 C5 I3 121.1(7) . . ?
F3 C6 C5 119.4(8) . . ?
F3 C6 C1 118.1(8) . . ?
C5 C6 C1 122.4(8) . . ?
N1 C7 C8 123.7(11) . . ?
C9 C8 C7 118.6(10) . . ?
C8 C9 C10 118.4(9) . . ?
C8 C9 C12 121.7(8) . . ?
C10 C9 C12 119.8(8) . . ?
C11 C10 C9 118.3(9) . . ?
N1 C11 C10 124.1(10) . . ?
N2 C12 O1 113.2(8) . . ?
N2 C12 C9 126.8(8) . . ?
O1 C12 C9 120.0(7) . . ?
N3 C13 O1 111.7(8) . . ?
N3 C13 C14 128.7(8) . . ?
O1 C13 C14 119.5(8) . . ?
C19 C14 C15 119.8(9) . . ?
C19 C14 C13 118.9(9) . . ?
C15 C14 C13 121.3(8) . . ?
C16 C15 C14 120.4(9) . . ?
C17 C16 C15 118.5(10) . . ?
O2 C17 C16 114.6(9) . . ?
O2 C17 C18 123.8(9) . . ?
C16 C17 C18 121.7(9) . . ?
C19 C18 C17 118.5(9) . . ?
C18 C19 C14 121.0(10) . . ?
O2 C20 C21 107.4(8) . . ?
C22 C21 C20 111.2(9) . . ?
C21 C22 C23 113.9(9) . . ?
C24 C23 C22 114.7(9) . . ?
C23 C24 C25 113.3(10) . . ?
C7 N1 C11 116.7(9) . . ?
C12 N2 N3 105.7(8) . . ?
C13 N3 N2 106.5(7) . . ?
C12 O1 C13 102.9(7) . . ?
C17 O2 C20 117.3(8) . . ?

_refine_diff_density_max         2.147
_refine_diff_density_min         -1.940
_refine_diff_density_rms         0.324




