# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ro34_olen
_database_code_depnum_ccdc_archive 'CCDC 1048779'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H25 Cl3 F10 N6 O2'
_chemical_formula_weight         990.07

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   13.6200(3)
_cell_length_b                   13.6200(3)
_cell_length_c                   22.0245(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4085.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3717
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      71.94

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.888
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.29
_diffrn_reflns_number            8246
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.245
_diffrn_reflns_theta_max         72.095
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4913
_reflns_number_gt                4476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    1.000

_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1232P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4913
_refine_ls_number_parameters     614
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_restrained_S_all      0.867
_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
Cl1 Cl 0.10639(10) 0.49967(11) 0.34075(9) 0.0348(3) Uani 1 1 d . . . . .
Cl2 Cl 0.30859(13) 0.44863(13) 0.36612(10) 0.0497(5) Uani 1 1 d . . . . .
Cl3 Cl 0.25139(11) 0.50570(12) 0.24530(9) 0.0404(4) Uani 1 1 d . . . . .
C2X C 0.2292(4) 0.5236(4) 0.3227(3) 0.0303(13) Uani 1 1 d . . . . .
H2X H 0.2435 0.5938 0.3327 0.036 Uiso 1 1 calc R U . . .
F6 F 0.2510(2) 0.5798(2) 0.05899(15) 0.0232(6) Uani 1 1 d . . . . .
F5 F -0.2891(2) 1.0854(2) 0.17535(15) 0.0262(7) Uani 1 1 d . . . . .
F2 F -0.3007(2) 0.9774(2) 0.41138(15) 0.0264(7) Uani 1 1 d . . . . .
F1 F -0.1959(2) 0.8685(2) 0.33257(15) 0.0225(6) Uani 1 1 d . . . . .
F8 F 0.4589(2) 0.5449(2) -0.10911(17) 0.0274(7) Uani 1 1 d . . . . .
F4 F -0.3989(2) 1.1868(2) 0.25232(17) 0.0307(7) Uani 1 1 d . . . . .
F10 F 0.1843(2) 0.7499(2) -0.12333(15) 0.0263(7) Uani 1 1 d . . . . .
F9 F 0.3411(2) 0.6648(2) -0.17532(15) 0.0275(7) Uani 1 1 d . . . . .
F7 F 0.4101(2) 0.4972(2) 0.00610(18) 0.0313(8) Uani 1 1 d . . . . .
F3 F -0.4059(2) 1.1337(3) 0.37271(17) 0.0328(8) Uani 1 1 d . . . . .
O2X O -0.1211(3) 0.4836(3) 0.33258(19) 0.0264(8) Uani 1 1 d . . . . .
C1X C -0.1264(3) 0.5033(4) 0.2783(3) 0.0204(10) Uani 1 1 d . . . . .
C19 C 0.1293(3) 0.7162(3) 0.0008(2) 0.0153(9) Uani 1 1 d . . . . .
N2 N -0.1528(3) 0.7706(3) 0.14248(19) 0.0149(8) Uani 1 1 d . . . . .
C60 C 0.3193(3) 0.6453(4) -0.1176(2) 0.0179(9) Uani 1 1 d . . . . .
C57 C 0.2720(3) 0.6007(3) 0.0005(2) 0.0172(9) Uani 1 1 d . . . . .
O1X O -0.1568(3) 0.4632(2) 0.17388(18) 0.0206(7) Uani 1 1 d . . . . .
N3 N -0.0367(3) 0.9260(3) 0.1417(2) 0.0163(8) Uani 1 1 d D . . . .
H1N3 H -0.057(4) 0.866(3) 0.129(3) 0.020 Uiso 1 1 d D U . . .
N4 N 0.0709(3) 0.8596(3) 0.0544(2) 0.0152(8) Uani 1 1 d D . . . .
H1N4 H 0.009(2) 0.866(4) 0.040(3) 0.018 Uiso 1 1 d D U . . .
C105 C -0.3207(3) 0.5089(4) 0.0469(3) 0.0216(10) Uani 1 1 d . . . . .
H105 H -0.3321 0.5583 0.0173 0.026 Uiso 1 1 calc R U . . .
C12 C -0.0486(3) 1.0607(3) 0.1978(2) 0.0159(9) Uani 1 1 d . . . . .
H12 H -0.0726 1.1084 0.2256 0.019 Uiso 1 1 calc R U . . .
C16 C 0.2095(3) 0.9440(3) 0.0727(2) 0.0173(10) Uani 1 1 d . . . . .
H16 H 0.2536 0.9930 0.0867 0.021 Uiso 1 1 calc R U . . .
C18 C 0.1459(3) 0.8090(3) 0.0260(2) 0.0161(9) Uani 1 1 d . . . . .
C14 C 0.0436(3) 0.9820(3) 0.1279(2) 0.0144(9) Uani 1 1 d . . . . .
C53 C -0.3529(4) 1.0822(4) 0.3330(3) 0.0217(10) Uani 1 1 d . . . . .
C52 C -0.3002(4) 1.0000(4) 0.3529(3) 0.0202(10) Uani 1 1 d . . . . .
C2 C 0.0168(3) 0.5699(3) -0.0167(3) 0.0188(10) Uani 1 1 d . . . . .
H2 H 0.0526 0.5364 -0.0474 0.023 Uiso 1 1 calc R U . . .
C51 C -0.2464(3) 0.9468(3) 0.3116(2) 0.0165(9) Uani 1 1 d . . . . .
N1X N -0.0981(3) 0.5884(3) 0.2527(2) 0.0196(9) Uani 1 1 d . . . . .
H1X H -0.1002 0.5934 0.2129 0.024 Uiso 1 1 calc R U . . .
C15 C 0.1081(3) 0.9400(3) 0.0845(3) 0.0155(9) Uani 1 1 d . . . . .
C5 C -0.1815(3) 0.6114(3) 0.0912(2) 0.0146(9) Uani 1 1 d . . . . .
C8 C -0.2920(3) 0.7713(3) 0.2030(2) 0.0162(9) Uani 1 1 d . . . . .
H8 H -0.3396 0.7915 0.2320 0.019 Uiso 1 1 calc R U . . .
C50 C -0.2399(3) 0.9718(3) 0.2505(2) 0.0147(9) Uani 1 1 d . . . . .
N1 N -0.0287(3) 0.6820(3) 0.0524(2) 0.0147(8) Uani 1 1 d D . . . .
H1N1 H -0.029(4) 0.738(3) 0.075(3) 0.018 Uiso 1 1 d D U . . .
C100 C -0.2464(3) 0.5217(3) 0.0894(3) 0.0178(9) Uani 1 1 d . . . . .
C61 C 0.2387(3) 0.6874(3) -0.0903(2) 0.0171(9) Uani 1 1 d . . . . .
N1Y N 0.1174(3) 0.8736(3) 0.2583(2) 0.0180(8) Uani 1 1 d . . . . .
C110 C 0.1580(4) 0.7422(4) 0.1906(3) 0.0239(11) Uani 1 1 d . . . . .
H110 H 0.1993 0.7171 0.1595 0.029 Uiso 1 1 calc R U . . .
C1 C 0.0444(3) 0.6596(3) 0.0110(2) 0.0160(9) Uani 1 1 d . . . . .
C108 C 0.0201(3) 0.7260(3) 0.2579(3) 0.0183(10) Uani 1 1 d . . . . .
C109 C 0.0785(4) 0.6864(4) 0.2127(3) 0.0227(11) Uani 1 1 d . . . . .
H109 H 0.0652 0.6229 0.1968 0.027 Uiso 1 1 calc R U . . .
C59 C 0.3773(3) 0.5815(3) -0.0847(3) 0.0186(10) Uani 1 1 d . . . . .
C107 C -0.0646(4) 0.6721(3) 0.2871(3) 0.0208(10) Uani 1 1 d . . . . .
H10A H -0.0442 0.6497 0.3280 0.025 Uiso 1 1 calc R U . . .
H10B H -0.1201 0.7183 0.2924 0.025 Uiso 1 1 calc R U . . .
C104 C -0.3783(4) 0.4250(4) 0.0471(3) 0.0274(12) Uani 1 1 d . . . . .
H104 H -0.4286 0.4173 0.0176 0.033 Uiso 1 1 calc R U . . .
C113 C 0.0421(3) 0.8199(4) 0.2778(3) 0.0197(10) Uani 1 1 d . . . . .
H113 H 0.0004 0.8480 0.3077 0.024 Uiso 1 1 calc R U . . .
C55 C -0.2917(3) 1.0556(4) 0.2332(2) 0.0181(9) Uani 1 1 d . . . . .
C4 C -0.1001(3) 0.6097(3) 0.0532(2) 0.0140(9) Uani 1 1 d . . . . .
C111 C 0.1749(3) 0.8336(4) 0.2149(2) 0.0199(10) Uani 1 1 d . . . . .
H111 H 0.2295 0.8703 0.2006 0.024 Uiso 1 1 calc R U . . .
C58 C 0.3523(3) 0.5584(3) -0.0258(3) 0.0203(10) Uani 1 1 d . . . . .
C11 C -0.0934(3) 0.9694(3) 0.1842(2) 0.0162(9) Uani 1 1 d . . . . .
C101 C -0.2325(3) 0.4477(4) 0.1330(2) 0.0185(9) Uani 1 1 d . . . . .
C10 C -0.1776(3) 0.9182(3) 0.2059(2) 0.0149(9) Uani 1 1 d . . . . .
C13 C 0.0368(3) 1.0682(3) 0.1634(3) 0.0176(9) Uani 1 1 d . . . . .
H13 H 0.0821 1.1213 0.1638 0.021 Uiso 1 1 calc R U . . .
C9 C -0.2044(3) 0.8249(3) 0.1851(2) 0.0154(9) Uani 1 1 d . . . . .
C6 C -0.2057(3) 0.6871(3) 0.1326(2) 0.0144(9) Uani 1 1 d . . . . .
C102 C -0.2893(4) 0.3634(4) 0.1338(3) 0.0256(11) Uani 1 1 d . . . . .
H102 H -0.2784 0.3140 0.1635 0.031 Uiso 1 1 calc R U . . .
C17 C 0.2337(3) 0.8633(3) 0.0368(2) 0.0179(9) Uani 1 1 d . . . . .
H17 H 0.2974 0.8473 0.0222 0.021 Uiso 1 1 calc R U . . .
C3 C -0.0702(3) 0.5395(3) 0.0082(3) 0.0191(10) Uani 1 1 d . . . . .
H3 H -0.1049 0.4816 -0.0025 0.023 Uiso 1 1 calc R U . . .
C7 C -0.2926(3) 0.6867(3) 0.1704(3) 0.0166(9) Uani 1 1 d . . . . .
H7 H -0.3411 0.6366 0.1720 0.020 Uiso 1 1 calc R U . . .
C106 C -0.1693(4) 0.4295(4) 0.2345(3) 0.0222(10) Uani 1 1 d . . . . .
H10C H -0.1361 0.3653 0.2397 0.027 Uiso 1 1 calc R U . . .
H10D H -0.2401 0.4204 0.2432 0.027 Uiso 1 1 calc R U . . .
C103 C -0.3630(4) 0.3522(4) 0.0901(3) 0.0263(12) Uani 1 1 d . . . . .
H103 H -0.4025 0.2948 0.0899 0.032 Uiso 1 1 calc R U . . .
C56 C 0.2125(3) 0.6677(3) -0.0306(2) 0.0152(9) Uani 1 1 d . . . . .
C54 C -0.3484(4) 1.1086(4) 0.2729(3) 0.0224(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
Cl1 C2X 1.750(6) . ?
Cl2 C2X 1.768(6) . ?
Cl3 C2X 1.748(7) . ?
F6 C57 1.351(6) . ?
F5 C55 1.337(6) . ?
F2 C52 1.324(7) . ?
F1 C51 1.350(5) . ?
F8 C59 1.333(6) . ?
F4 C54 1.346(6) . ?
F10 C61 1.343(6) . ?
F9 C60 1.333(6) . ?
F7 C58 1.344(6) . ?
F3 C53 1.333(6) . ?
O2X C1X 1.228(7) . ?
C1X N1X 1.345(7) . ?
C1X C106 1.511(7) . ?
C19 C18 1.398(7) . ?
C19 C1 1.408(6) . ?
C19 C56 1.484(6) . ?
N2 C6 1.365(6) . ?
N2 C9 1.386(6) . ?
C60 C61 1.377(7) . ?
C60 C59 1.380(7) . ?
C57 C58 1.366(7) . ?
C57 C56 1.399(7) . ?
O1X C101 1.386(6) . ?
O1X C106 1.423(7) . ?
N3 C11 1.350(6) . ?
N3 C14 1.368(6) . ?
N4 C15 1.376(6) . ?
N4 C18 1.383(6) . ?
C105 C104 1.386(7) . ?
C105 C100 1.389(8) . ?
C12 C13 1.392(7) . ?
C12 C11 1.417(6) . ?
C16 C17 1.393(7) . ?
C16 C15 1.406(6) . ?
C18 C17 1.427(6) . ?
C14 C13 1.414(7) . ?
C14 C15 1.419(7) . ?
C53 C54 1.375(8) . ?
C53 C52 1.401(7) . ?
C52 C51 1.375(7) . ?
C2 C3 1.369(7) . ?
C2 C1 1.416(6) . ?
C51 C50 1.390(7) . ?
N1X C107 1.443(6) . ?
C5 C4 1.389(7) . ?
C5 C6 1.414(7) . ?
C5 C100 1.509(6) . ?
C8 C7 1.358(7) . ?
C8 C9 1.454(6) . ?
C50 C55 1.395(6) . ?
C50 C10 1.489(6) . ?
N1 C1 1.384(6) . ?
N1 C4 1.385(6) . ?
C100 C101 1.404(7) . ?
C61 C56 1.387(7) . ?
N1Y C113 1.331(7) . ?
N1Y C111 1.350(7) . ?
C110 C111 1.374(7) . ?
C110 C109 1.410(7) . ?
C108 C109 1.384(8) . ?
C108 C113 1.386(7) . ?
C108 C107 1.512(7) . ?
C59 C58 1.376(8) . ?
C104 C103 1.387(9) . ?
C55 C54 1.371(7) . ?
C4 C3 1.437(7) . ?
C11 C10 1.424(6) . ?
C101 C102 1.384(7) . ?
C10 C9 1.400(7) . ?
C6 C7 1.447(6) . ?
C102 C103 1.398(9) . ?

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
Cl3 C2X Cl1 111.1(3) . . ?
Cl3 C2X Cl2 109.9(3) . . ?
Cl1 C2X Cl2 110.7(4) . . ?
O2X C1X N1X 125.4(5) . . ?
O2X C1X C106 119.9(5) . . ?
N1X C1X C106 114.7(5) . . ?
C18 C19 C1 124.4(4) . . ?
C18 C19 C56 117.6(4) . . ?
C1 C19 C56 117.2(4) . . ?
C6 N2 C9 106.6(4) . . ?
F9 C60 C61 120.8(5) . . ?
F9 C60 C59 120.0(4) . . ?
C61 C60 C59 119.3(5) . . ?
F6 C57 C58 119.0(4) . . ?
F6 C57 C56 118.8(4) . . ?
C58 C57 C56 122.1(5) . . ?
C101 O1X C106 118.1(4) . . ?
C11 N3 C14 111.5(4) . . ?
C15 N4 C18 110.1(4) . . ?
C104 C105 C100 120.9(5) . . ?
C13 C12 C11 108.0(4) . . ?
C17 C16 C15 107.9(4) . . ?
N4 C18 C19 120.7(4) . . ?
N4 C18 C17 106.5(4) . . ?
C19 C18 C17 132.2(4) . . ?
N3 C14 C13 106.7(4) . . ?
N3 C14 C15 114.8(4) . . ?
C13 C14 C15 138.5(4) . . ?
F3 C53 C54 121.3(5) . . ?
F3 C53 C52 119.6(5) . . ?
C54 C53 C52 119.1(5) . . ?
F2 C52 C51 121.6(5) . . ?
F2 C52 C53 119.1(5) . . ?
C51 C52 C53 119.2(5) . . ?
C3 C2 C1 108.5(4) . . ?
F1 C51 C52 117.4(5) . . ?
F1 C51 C50 119.5(4) . . ?
C52 C51 C50 123.1(5) . . ?
C1X N1X C107 123.5(5) . . ?
N4 C15 C16 107.6(4) . . ?
N4 C15 C14 114.7(4) . . ?
C16 C15 C14 135.8(5) . . ?
C4 C5 C6 125.9(4) . . ?
C4 C5 C100 115.9(4) . . ?
C6 C5 C100 118.1(4) . . ?
C7 C8 C9 106.7(4) . . ?
C51 C50 C55 115.7(4) . . ?
C51 C50 C10 123.7(4) . . ?
C55 C50 C10 120.5(5) . . ?
C1 N1 C4 110.9(4) . . ?
C105 C100 C101 117.9(4) . . ?
C105 C100 C5 123.1(5) . . ?
C101 C100 C5 119.0(4) . . ?
F10 C61 C60 117.8(5) . . ?
F10 C61 C56 119.7(4) . . ?
C60 C61 C56 122.5(5) . . ?
C113 N1Y C111 117.0(4) . . ?
C111 C110 C109 118.9(5) . . ?
N1 C1 C19 125.0(4) . . ?
N1 C1 C2 106.5(4) . . ?
C19 C1 C2 128.5(5) . . ?
C109 C108 C113 117.6(5) . . ?
C109 C108 C107 123.8(4) . . ?
C113 C108 C107 118.6(5) . . ?
C108 C109 C110 118.6(5) . . ?
F8 C59 C58 120.0(5) . . ?
F8 C59 C60 120.1(5) . . ?
C58 C59 C60 119.8(5) . . ?
N1X C107 C108 113.6(5) . . ?
C105 C104 C103 120.4(5) . . ?
N1Y C113 C108 124.8(5) . . ?
F5 C55 C54 117.5(4) . . ?
F5 C55 C50 119.7(4) . . ?
C54 C55 C50 122.7(5) . . ?
N1 C4 C5 123.8(4) . . ?
N1 C4 C3 105.3(4) . . ?
C5 C4 C3 130.8(4) . . ?
N1Y C111 C110 122.9(5) . . ?
F7 C58 C57 120.6(5) . . ?
F7 C58 C59 119.3(4) . . ?
C57 C58 C59 120.0(5) . . ?
N3 C11 C12 106.5(4) . . ?
N3 C11 C10 118.6(4) . . ?
C12 C11 C10 134.9(5) . . ?
C102 C101 O1X 122.3(5) . . ?
C102 C101 C100 121.9(5) . . ?
O1X C101 C100 115.8(4) . . ?
C9 C10 C11 123.0(4) . . ?
C9 C10 C50 120.8(4) . . ?
C11 C10 C50 116.1(4) . . ?
C12 C13 C14 107.1(4) . . ?
N2 C9 C10 125.1(4) . . ?
N2 C9 C8 109.4(4) . . ?
C10 C9 C8 125.5(4) . . ?
N2 C6 C5 126.0(4) . . ?
N2 C6 C7 110.0(4) . . ?
C5 C6 C7 124.0(4) . . ?
C101 C102 C103 118.9(5) . . ?
C16 C17 C18 107.8(4) . . ?
C2 C3 C4 108.7(4) . . ?
C8 C7 C6 107.3(4) . . ?
O1X C106 C1X 109.7(4) . . ?
C104 C103 C102 120.0(5) . . ?
C61 C56 C57 116.2(4) . . ?
C61 C56 C19 123.5(4) . . ?
C57 C56 C19 120.3(5) . . ?
F4 C54 C55 119.3(5) . . ?
F4 C54 C53 120.5(5) . . ?
C55 C54 C53 120.2(5) . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_ro41_olen
_database_code_depnum_ccdc_archive 'CCDC 1048780'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H28 Cl3 F10 N5 O2'
_chemical_formula_weight         955.06

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'
Cl Cl 0.3639 0.7018 '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                   11.0840(9)
_cell_length_b                   13.9124(12)
_cell_length_c                   15.6917(13)
_cell_angle_alpha                95.169(7)
_cell_angle_beta                 107.245(7)
_cell_angle_gamma                111.916(8)
_cell_volume                     2088.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4699
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      72.08

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.792
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.29
_diffrn_reflns_number            14457
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.516
_diffrn_reflns_theta_max         72.226
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7973
_reflns_number_gt                5976
_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 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    ?
_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)+(0.1612P)²+6.2961P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7973
_refine_ls_number_parameters     587
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0992
_refine_ls_wR_factor_ref         0.3135
_refine_ls_wR_factor_gt          0.2952
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O1 O 0.6331(3) 0.1035(2) 0.4865(2) 0.0268(7) Uani 1 1 d . . . . .
O2 O 0.5316(4) 0.2719(3) 0.6046(3) 0.0368(8) Uani 1 1 d . . . . .
N5 N 0.6611(5) 0.1826(4) 0.6592(3) 0.0415(11) Uani 1 1 d . . . . .
H5 H 0.6868 0.1328 0.6443 0.050 Uiso 1 1 calc R U . . .
C50 C 0.5324(5) 0.1395(4) 0.4972(3) 0.0293(10) Uani 1 1 d . . . . .
H50A H 0.4431 0.0770 0.4837 0.035 Uiso 1 1 calc R U . . .
H50B H 0.5167 0.1829 0.4520 0.035 Uiso 1 1 calc R U . . .
C51 C 0.5760(5) 0.2049(4) 0.5925(4) 0.0312(10) Uani 1 1 d . . . . .
C53 C 0.7141(8) 0.2362(6) 0.7557(4) 0.0564(17) Uani 1 1 d . . . . .
H53A H 0.7212 0.3096 0.7592 0.068 Uiso 1 1 calc R U . . .
H53B H 0.8094 0.2413 0.7845 0.068 Uiso 1 1 calc R U . . .
C55 C 0.6069(10) 0.0753(9) 0.8103(6) 0.084(3) Uani 1 1 d . . . . .
H55A H 0.6964 0.0693 0.8226 0.101 Uiso 1 1 calc R U . . .
H55B H 0.5423 0.0296 0.7491 0.101 Uiso 1 1 calc R U . . .
C54 C 0.6291(9) 0.1840(8) 0.8104(5) 0.072(2) Uani 1 1 d . . . . .
H54A H 0.6757 0.2258 0.8745 0.086 Uiso 1 1 calc R U . . .
H54B H 0.5373 0.1865 0.7862 0.086 Uiso 1 1 calc R U . . .
C56 C 0.5429(12) 0.0346(11) 0.8868(9) 0.115(4) Uani 1 1 d . . . . .
H56A H 0.6018 0.0842 0.9463 0.173 Uiso 1 1 calc R U . . .
H56B H 0.5393 -0.0362 0.8907 0.173 Uiso 1 1 calc R U . . .
H56C H 0.4486 0.0312 0.8700 0.173 Uiso 1 1 calc R U . . .
Cl2 Cl 0.9918(3) 0.49174(18) 0.28677(18) 0.0833(7) Uani 1 1 d . . . . .
Cl1 Cl 0.9629(4) 0.3685(3) 0.11873(19) 0.1137(11) Uani 1 1 d . . . . .
Cl3 Cl 0.7554(3) 0.2877(2) 0.20192(19) 0.0965(8) Uani 1 1 d . . . . .
C1X C 0.9293(10) 0.3629(7) 0.2219(6) 0.076(2) Uani 1 1 d . . . . .
H1X H 0.9832 0.3269 0.2577 0.091 Uiso 1 1 calc R U . . .
F10 F 1.0459(3) -0.1369(3) 0.8265(2) 0.0421(7) Uani 1 1 d . . . . .
F8 F 0.8994(4) -0.1154(3) 1.07539(19) 0.0489(9) Uani 1 1 d . . . . .
F6 F 0.5802(3) -0.1973(3) 0.7771(2) 0.0447(8) Uani 1 1 d . . . . .
N2 N 0.7646(4) -0.1467(3) 0.3727(2) 0.0229(8) Uani 1 1 d D . . . .
H1N2 H 0.767(6) -0.179(4) 0.419(3) 0.028 Uiso 1 1 d D U . . .
F9 F 1.1017(4) -0.1049(3) 1.0089(2) 0.0506(9) Uani 1 1 d . . . . .
F7 F 0.6386(4) -0.1612(3) 0.9598(2) 0.0529(9) Uani 1 1 d . . . . .
N1 N 0.7903(4) -0.1063(3) 0.5623(2) 0.0219(7) Uani 1 1 d . . . . .
N4 N 0.6925(4) -0.3135(3) 0.5543(2) 0.0243(8) Uani 1 1 d D . . . .
H1N4 H 0.705(6) -0.260(3) 0.525(3) 0.029 Uiso 1 1 d D U . . .
F5 F 0.9375(4) -0.3100(3) 0.2188(2) 0.0492(8) Uani 1 1 d . . . . .
F1 F 0.4761(4) -0.3502(3) 0.0839(2) 0.0561(10) Uani 1 1 d . . . . .
C15 C 0.6653(5) -0.4156(3) 0.5191(3) 0.0242(9) Uani 1 1 d . . . . .
C14 C 0.6518(5) -0.4390(3) 0.4267(3) 0.0234(9) Uani 1 1 d . . . . .
F4 F 0.9411(5) -0.3683(4) 0.0519(3) 0.0761(13) Uani 1 1 d . . . . .
N3 N 0.6540(4) -0.3582(3) 0.3810(2) 0.0246(8) Uani 1 1 d D . . . .
H1N3 H 0.604(5) -0.321(4) 0.385(4) 0.030 Uiso 1 1 d D U . . .
C26 C 0.8466(5) 0.1391(3) 0.4636(3) 0.0220(9) Uani 1 1 d . . . . .
C2 C 0.8653(5) 0.0102(3) 0.7007(3) 0.0265(9) Uani 1 1 d . . . . .
H2A H 0.8902 0.0366 0.7643 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8287(4) -0.0050(3) 0.5500(3) 0.0218(8) Uani 1 1 d . . . . .
C1 C 0.8094(5) -0.1002(3) 0.6541(3) 0.0225(9) Uani 1 1 d . . . . .
F2 F 0.4832(5) -0.4033(3) -0.0828(2) 0.0742(14) Uani 1 1 d . . . . .
C13 C 0.6637(5) -0.5160(3) 0.3702(3) 0.0276(10) Uani 1 1 d . . . . .
H13 H 0.6612 -0.5822 0.3824 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7934(5) -0.0404(3) 0.3833(3) 0.0239(9) Uani 1 1 d . . . . .
C3 C 0.8755(5) 0.0688(3) 0.6365(3) 0.0242(9) Uani 1 1 d . . . . .
H3A H 0.9073 0.1438 0.6463 0.029 Uiso 1 1 calc R U . . .
C5 C 0.8217(5) 0.0262(3) 0.4656(3) 0.0220(8) Uani 1 1 d . . . . .
C10 C 0.7040(5) -0.2993(4) 0.2499(3) 0.0264(9) Uani 1 1 d . . . . .
C19 C 0.7805(5) -0.1875(3) 0.6955(3) 0.0239(9) Uani 1 1 d . . . . .
C25 C 0.9429(6) -0.1452(4) 0.8574(3) 0.0318(10) Uani 1 1 d . . . . .
C18 C 0.7270(5) -0.2937(3) 0.6471(3) 0.0244(9) Uani 1 1 d . . . . .
C9 C 0.7397(5) -0.1924(3) 0.2836(3) 0.0252(9) Uani 1 1 d . . . . .
F3 F 0.7143(6) -0.4148(3) -0.1003(2) 0.0761(14) Uani 1 1 d . . . . .
C16 C 0.6752(5) -0.4667(3) 0.5940(3) 0.0274(9) Uani 1 1 d . . . . .
H16 H 0.6586 -0.5393 0.5906 0.033 Uiso 1 1 calc R U . . .
C32 C 0.7061(5) -0.3300(3) 0.1570(3) 0.0290(10) Uani 1 1 d . . . . .
C11 C 0.6759(5) -0.3783(3) 0.3007(3) 0.0261(9) Uani 1 1 d . . . . .
C17 C 0.7131(5) -0.3921(3) 0.6725(3) 0.0270(9) Uani 1 1 d . . . . .
H17 H 0.7274 -0.4042 0.7326 0.032 Uiso 1 1 calc R U . . .
C22 C 0.7387(6) -0.1559(4) 0.9263(3) 0.0372(12) Uani 1 1 d . . . . .
C21 C 0.7091(6) -0.1742(4) 0.8325(3) 0.0322(11) Uani 1 1 d . . . . .
C8 C 0.7542(5) -0.1075(4) 0.2360(3) 0.0275(9) Uani 1 1 d . . . . .
H8 H 0.7438 -0.1138 0.1732 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7852(5) -0.0171(3) 0.2949(3) 0.0267(9) Uani 1 1 d . . . . .
H7 H 0.7991 0.0502 0.2804 0.032 Uiso 1 1 calc R U . . .
C28 C 0.7769(5) 0.2830(4) 0.4792(3) 0.0299(10) Uani 1 1 d . . . . .
H28 H 0.7150 0.3095 0.4917 0.036 Uiso 1 1 calc R U . . .
C37 C 0.8216(6) -0.3347(4) 0.1454(3) 0.0380(12) Uani 1 1 d . . . . .
C33 C 0.5929(7) -0.3537(4) 0.0787(3) 0.0407(13) Uani 1 1 d . . . . .
C23 C 0.8703(6) -0.1333(4) 0.9845(3) 0.0367(12) Uani 1 1 d . . . . .
C31 C 0.9623(5) 0.2085(4) 0.4488(3) 0.0277(9) Uani 1 1 d . . . . .
H31 H 1.0272 0.1835 0.4393 0.033 Uiso 1 1 calc R U . . .
C20 C 0.8118(5) -0.1685(3) 0.7960(3) 0.0260(9) Uani 1 1 d . . . . .
C27 C 0.7516(5) 0.1771(3) 0.4770(3) 0.0239(9) Uani 1 1 d . . . . .
C24 C 0.9733(6) -0.1277(4) 0.9512(3) 0.0347(11) Uani 1 1 d . . . . .
C34 C 0.5949(8) -0.3822(4) -0.0081(3) 0.0509(17) Uani 1 1 d . . . . .
C30 C 0.9858(5) 0.3132(4) 0.4473(4) 0.0337(11) Uani 1 1 d . . . . .
H30 H 1.0646 0.3591 0.4357 0.040 Uiso 1 1 calc R U . . .
C29 C 0.8921(5) 0.3497(4) 0.4631(4) 0.0355(11) Uani 1 1 d . . . . .
H29 H 0.9074 0.4216 0.4629 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6796(5) -0.4790(3) 0.2931(3) 0.0275(10) Uani 1 1 d . . . . .
H12 H 0.6910 -0.5152 0.2439 0.033 Uiso 1 1 calc R U . . .
C35 C 0.7112(8) -0.3888(5) -0.0163(4) 0.0536(17) Uani 1 1 d . . . . .
C36 C 0.8260(7) -0.3653(5) 0.0597(4) 0.0469(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
O1 C27 1.391(6) . ?
O1 C50 1.427(5) . ?
O2 C51 1.230(6) . ?
N5 C51 1.331(6) . ?
N5 C53 1.462(7) . ?
C50 C51 1.516(7) . ?
C53 C54 1.494(11) . ?
C55 C54 1.439(13) . ?
C55 C56 1.610(13) . ?
Cl2 C1X 1.748(9) . ?
Cl1 C1X 1.767(9) . ?
Cl3 C1X 1.728(10) . ?
F10 C25 1.338(6) . ?
F8 C23 1.344(5) . ?
F6 C21 1.331(6) . ?
N2 C6 1.374(5) . ?
N2 C9 1.383(5) . ?
F9 C24 1.338(6) . ?
F7 C22 1.343(7) . ?
N1 C4 1.362(5) . ?
N1 C1 1.382(5) . ?
N4 C15 1.360(5) . ?
N4 C18 1.365(5) . ?
F5 C37 1.348(6) . ?
F1 C33 1.340(7) . ?
C15 C14 1.407(6) . ?
C15 C16 1.425(6) . ?
C14 N3 1.383(5) . ?
C14 C13 1.399(6) . ?
F4 C36 1.332(8) . ?
N3 C11 1.376(6) . ?
C26 C31 1.387(7) . ?
C26 C27 1.400(6) . ?
C26 C5 1.495(5) . ?
C2 C3 1.357(6) . ?
C2 C1 1.447(6) . ?
C4 C5 1.421(6) . ?
C4 C3 1.448(6) . ?
C1 C19 1.406(6) . ?
F2 C34 1.341(7) . ?
C13 C12 1.388(6) . ?
C6 C5 1.397(6) . ?
C6 C7 1.437(6) . ?
C10 C9 1.395(6) . ?
C10 C11 1.410(6) . ?
C10 C32 1.490(6) . ?
C19 C18 1.410(6) . ?
C19 C20 1.487(6) . ?
C25 C24 1.386(7) . ?
C25 C20 1.380(7) . ?
C18 C17 1.426(6) . ?
C9 C8 1.438(6) . ?
F3 C35 1.349(6) . ?
C16 C17 1.381(6) . ?
C32 C37 1.370(8) . ?
C32 C33 1.377(7) . ?
C11 C12 1.413(6) . ?
C22 C23 1.369(8) . ?
C22 C21 1.387(6) . ?
C21 C20 1.399(7) . ?
C8 C7 1.354(6) . ?
C28 C29 1.379(7) . ?
C28 C27 1.388(6) . ?
C37 C36 1.394(7) . ?
C33 C34 1.393(8) . ?
C23 C24 1.370(8) . ?
C31 C30 1.384(6) . ?
C34 C35 1.368(11) . ?
C30 C29 1.387(7) . ?
C35 C36 1.366(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
C27 O1 C50 117.6(3) . . ?
C51 N5 C53 123.7(5) . . ?
O1 C50 C51 113.0(4) . . ?
O2 C51 N5 124.3(5) . . ?
O2 C51 C50 120.4(4) . . ?
N5 C51 C50 115.3(4) . . ?
N5 C53 C54 115.5(6) . . ?
C54 C55 C56 110.9(8) . . ?
C55 C54 C53 115.0(7) . . ?
Cl3 C1X Cl2 112.9(5) . . ?
Cl3 C1X Cl1 111.8(5) . . ?
Cl2 C1X Cl1 109.8(5) . . ?
C6 N2 C9 111.3(3) . . ?
C4 N1 C1 106.7(3) . . ?
C15 N4 C18 111.6(3) . . ?
N4 C15 C14 115.9(4) . . ?
N4 C15 C16 106.3(4) . . ?
C14 C15 C16 137.3(4) . . ?
N3 C14 C13 106.6(4) . . ?
N3 C14 C15 115.6(4) . . ?
C13 C14 C15 136.3(4) . . ?
C11 N3 C14 110.6(3) . . ?
C31 C26 C27 118.4(4) . . ?
C31 C26 C5 121.8(4) . . ?
C27 C26 C5 119.8(4) . . ?
C3 C2 C1 107.1(4) . . ?
N1 C4 C5 126.2(4) . . ?
N1 C4 C3 110.0(4) . . ?
C5 C4 C3 123.7(4) . . ?
N1 C1 C19 125.1(4) . . ?
N1 C1 C2 109.2(4) . . ?
C19 C1 C2 125.6(4) . . ?
C12 C13 C14 108.3(4) . . ?
N2 C6 C5 124.2(4) . . ?
N2 C6 C7 106.1(3) . . ?
C5 C6 C7 129.7(4) . . ?
C2 C3 C4 106.8(4) . . ?
C6 C5 C4 125.2(4) . . ?
C6 C5 C26 116.8(4) . . ?
C4 C5 C26 118.0(4) . . ?
C9 C10 C11 124.0(4) . . ?
C9 C10 C32 117.7(4) . . ?
C11 C10 C32 118.2(4) . . ?
C1 C19 C18 123.5(4) . . ?
C1 C19 C20 119.2(4) . . ?
C18 C19 C20 117.3(4) . . ?
F10 C25 C24 118.0(5) . . ?
F10 C25 C20 119.8(4) . . ?
C24 C25 C20 122.2(5) . . ?
N4 C18 C19 118.3(4) . . ?
N4 C18 C17 106.3(4) . . ?
C19 C18 C17 134.9(4) . . ?
N2 C9 C10 125.6(4) . . ?
N2 C9 C8 105.2(4) . . ?
C10 C9 C8 129.2(4) . . ?
C17 C16 C15 108.0(4) . . ?
C37 C32 C33 116.7(5) . . ?
C37 C32 C10 121.5(4) . . ?
C33 C32 C10 121.8(5) . . ?
N3 C11 C10 120.5(4) . . ?
N3 C11 C12 106.2(4) . . ?
C10 C11 C12 132.8(4) . . ?
C16 C17 C18 107.7(4) . . ?
F7 C22 C23 120.3(4) . . ?
F7 C22 C21 120.1(5) . . ?
C23 C22 C21 119.5(5) . . ?
F6 C21 C22 118.7(5) . . ?
F6 C21 C20 120.1(4) . . ?
C22 C21 C20 121.2(5) . . ?
C7 C8 C9 109.2(4) . . ?
C8 C7 C6 108.2(4) . . ?
C29 C28 C27 120.0(4) . . ?
F5 C37 C32 120.0(4) . . ?
F5 C37 C36 117.1(5) . . ?
C32 C37 C36 122.9(5) . . ?
F1 C33 C32 120.6(5) . . ?
F1 C33 C34 117.6(5) . . ?
C32 C33 C34 121.8(6) . . ?
F8 C23 C22 119.7(5) . . ?
F8 C23 C24 119.4(5) . . ?
C22 C23 C24 120.9(4) . . ?
C30 C31 C26 121.8(4) . . ?
C25 C20 C21 117.1(4) . . ?
C25 C20 C19 121.6(4) . . ?
C21 C20 C19 121.3(4) . . ?
C28 C27 O1 123.3(4) . . ?
C28 C27 C26 120.2(4) . . ?
O1 C27 C26 116.5(4) . . ?
F9 C24 C23 120.2(4) . . ?
F9 C24 C25 120.7(5) . . ?
C23 C24 C25 119.1(5) . . ?
F2 C34 C35 120.5(5) . . ?
F2 C34 C33 120.0(7) . . ?
C35 C34 C33 119.4(6) . . ?
C31 C30 C29 118.7(5) . . ?
C28 C29 C30 120.8(4) . . ?
C13 C12 C11 108.2(4) . . ?
F3 C35 C36 119.8(7) . . ?
F3 C35 C34 119.6(6) . . ?
C36 C35 C34 120.6(5) . . ?
F4 C36 C35 120.8(5) . . ?
F4 C36 C37 120.7(6) . . ?
C35 C36 C37 118.5(6) . . ?

_refine_diff_density_max         0.901
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.118

_shelxl_version_number           2013-3

