# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_apy_1b
_database_code_depnum_ccdc_archive 'CCDC 1868141'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2018-09-17 deposited with the CCDC.	2019-03-12 downloaded from the CCDC.
;
_audit_creation_date             2018-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 F8 I2 O4, C10 H8 N4'
_chemical_formula_sum            'C32 H24 F8 I2 N4 O4'
_chemical_formula_weight         934.35
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   10.4002(10)
_cell_length_b                   13.3883(13)
_cell_length_c                   14.2970(14)
_cell_angle_alpha                68.135(8)
_cell_angle_beta                 70.540(8)
_cell_angle_gamma                69.104(7)
_cell_volume                     1679.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    84467
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.68
_cell_measurement_theta_min      2.15
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.493
_exptl_absorpt_coefficient_mu    1.961
_exptl_absorpt_correction_T_max  0.7170
_exptl_absorpt_correction_T_min  0.3572
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
'STOE X-Red32, absorption correction by Gaussian integration, analogous to P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis", published in F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard, Copenhagen (1970), 255 - 270'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44176
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.477
_diffrn_reflns_theta_min         2.154
_diffrn_ambient_temperature      119.99
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                16177
_reflns_number_total             17217
_reflns_special_details          'Friedel pairs have not been merged'
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_data_reduction        
'X-Area Integrate 1.72.0.0 (STOE, 2018) X-Area X-Red32 1.63.4.0 (STOE, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.559
_refine_diff_density_min         -1.765
_refine_diff_density_rms         0.165
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     901
_refine_ls_number_reflns         17211
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0972P)²+1.7781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1365
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C40(H40), C41(H41)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B), C39(H39A,H39B), C42(H42A,H42B), C50(H50A,H50B),
  C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31),
 C32(H32), C56(H56), C57(H57), C58(H58), C59(H59), C61(H61), C62(H62), C63(H63),
  C64(H64)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
I1 I 0.01129(4) 0.39000(3) 0.42976(3) 0.02793(12) Uani 1 1 d . . . . .
I2 I 1.60681(4) -0.08342(4) -0.03516(3) 0.02979(12) Uani 1 1 d . . . . .
F6 F 1.5100(5) 0.1860(5) -0.1119(4) 0.0360(11) Uani 1 1 d . . . . .
F5 F 1.2563(5) 0.3330(4) -0.0966(4) 0.0316(10) Uani 1 1 d . . . . .
F8 F 1.0399(5) 0.0411(5) 0.1064(4) 0.0382(11) Uani 1 1 d . . . . .
F7 F 1.2944(6) -0.1088(5) 0.0901(5) 0.0414(12) Uani 1 1 d . . . . .
F1 F 0.1232(5) 0.3869(4) 0.1926(4) 0.0320(10) Uani 1 1 d . . . . .
F2 F 0.3714(5) 0.2904(4) 0.0846(3) 0.0305(9) Uani 1 1 d . . . . .
F4 F 0.3104(6) 0.2352(5) 0.4917(3) 0.0367(11) Uani 1 1 d . . . . .
F3 F 0.5614(5) 0.1525(4) 0.3795(4) 0.0340(10) Uani 1 1 d . . . . .
O1 O 1.0106(6) 0.2618(5) 0.0097(4) 0.0291(11) Uani 1 1 d . . . . .
O2 O 0.7754(6) 0.4743(5) 0.1307(5) 0.0302(11) Uani 1 1 d . . . . .
O3 O 0.5957(5) 0.3903(5) 0.1884(4) 0.0271(10) Uani 1 1 d . . . . .
O7 O 0.6019(5) 0.1729(4) 0.1748(4) 0.0252(10) Uani 1 1 d . . . . .
C1 C 0.2078(7) 0.3169(7) 0.3454(6) 0.0236(13) Uani 1 1 d . . . . .
C2 C 0.2289(7) 0.3282(6) 0.2414(5) 0.0220(12) Uani 1 1 d . . . . .
C3 C 0.3576(7) 0.2794(6) 0.1850(5) 0.0215(12) Uani 1 1 d . . . . .
C4 C 0.4731(7) 0.2196(6) 0.2293(5) 0.0215(12) Uani 1 1 d . . . . .
C5 C 0.4514(8) 0.2074(6) 0.3337(6) 0.0240(13) Uani 1 1 d . . . . .
C6 C 0.3231(8) 0.2518(7) 0.3904(5) 0.0252(13) Uani 1 1 d . . . . .
C7 C 0.6801(7) 0.2520(6) 0.1002(5) 0.0255(12) Uani 1 1 d . . . . .
H7A H 0.621481 0.307514 0.051652 0.031 Uiso 1 1 calc R . . . .
H7B H 0.766923 0.211814 0.059430 0.031 Uiso 1 1 calc R . . . .
C8 C 0.7202(7) 0.3117(6) 0.1533(5) 0.0216(12) Uani 1 1 d . . . . .
H8 H 0.762170 0.257286 0.212577 0.026 Uiso 1 1 calc R . . . .
C9 C 0.8163(7) 0.3886(5) 0.0817(5) 0.0235(11) Uani 1 1 d . . . . .
H9 H 0.795678 0.421208 0.011253 0.028 Uiso 1 1 calc R . . . .
C10 C 0.9725(7) 0.3349(6) 0.0731(5) 0.0243(13) Uani 1 1 d . . . . .
H10A H 1.026151 0.392116 0.040137 0.029 Uiso 1 1 calc R . . . .
H10B H 0.992237 0.292005 0.142395 0.029 Uiso 1 1 calc R . . . .
C11 C 1.1424(7) 0.1902(6) 0.0058(6) 0.0241(13) Uani 1 1 d . . . . .
C12 C 1.2650(8) 0.2244(7) -0.0494(6) 0.0251(13) Uani 1 1 d . . . . .
C13 C 1.3969(8) 0.1460(7) -0.0572(6) 0.0268(14) Uani 1 1 d . . . . .
C14 C 1.4099(7) 0.0351(7) -0.0119(6) 0.0269(14) Uani 1 1 d . . . . .
C15 C 1.2871(9) 0.0007(7) 0.0444(6) 0.0274(14) Uani 1 1 d . . . . .
C16 C 1.1560(8) 0.0769(7) 0.0526(6) 0.0264(14) Uani 1 1 d . . . . .
C17 C 0.6393(7) 0.4721(6) 0.2011(6) 0.0243(13) Uani 1 1 d . . . . .
C18 C 0.6535(8) 0.4433(7) 0.3119(6) 0.0271(15) Uani 1 1 d . . . . .
H18A H 0.718738 0.368001 0.330688 0.033 Uiso 1 1 calc R . . . .
H18B H 0.693946 0.497601 0.316316 0.033 Uiso 1 1 calc R . . . .
C19 C 0.5095(10) 0.4459(8) 0.3873(6) 0.0350(17) Uani 1 1 d . . . . .
H19A H 0.475226 0.384874 0.389246 0.042 Uiso 1 1 calc R . . . .
H19B H 0.519494 0.432843 0.457733 0.042 Uiso 1 1 calc R . . . .
C20 C 0.4014(11) 0.5564(9) 0.3572(8) 0.044(2) Uani 1 1 d . . . . .
H20A H 0.429567 0.616294 0.363861 0.053 Uiso 1 1 calc R . . . .
H20B H 0.308223 0.552617 0.405371 0.053 Uiso 1 1 calc R . . . .
C21 C 0.3880(10) 0.5853(9) 0.2470(8) 0.043(2) Uani 1 1 d . . . . .
H21A H 0.321537 0.660127 0.228717 0.052 Uiso 1 1 calc R . . . .
H21B H 0.348915 0.530455 0.242126 0.052 Uiso 1 1 calc R . . . .
C22 C 0.5321(8) 0.5848(7) 0.1705(6) 0.0303(15) Uani 1 1 d . . . . .
H22A H 0.522004 0.599147 0.099872 0.036 Uiso 1 1 calc R . . . .
H22B H 0.566609 0.645043 0.169979 0.036 Uiso 1 1 calc R . . . .
I3 I -0.16451(4) 0.40044(4) 0.78940(3) 0.03087(12) Uani 1 1 d . . . . .
I4 I 1.45020(4) -0.06587(3) 0.32795(3) 0.02605(11) Uani 1 1 d . . . . .
F12 F -0.0525(5) 0.1295(5) 0.8670(4) 0.0376(11) Uani 1 1 d . . . . .
F11 F 0.2047(5) -0.0088(4) 0.8458(4) 0.0335(10) Uani 1 1 d . . . . .
F9 F 0.1407(6) 0.4352(4) 0.6620(4) 0.0396(11) Uani 1 1 d . . . . .
F10 F 0.3982(5) 0.2957(4) 0.6384(4) 0.0356(11) Uani 1 1 d . . . . .
F15 F 1.3181(5) -0.0534(5) 0.5640(4) 0.0370(11) Uani 1 1 d . . . . .
F16 F 1.0600(6) 0.0379(5) 0.6621(4) 0.0364(10) Uani 1 1 d . . . . .
F13 F 0.9084(5) 0.1809(5) 0.3492(4) 0.0402(12) Uani 1 1 d . . . . .
F14 F 1.1646(5) 0.0884(5) 0.2518(4) 0.0346(10) Uani 1 1 d . . . . .
O4 O 0.4444(6) 0.0778(5) 0.7294(5) 0.0313(11) Uani 1 1 d . . . . .
O5 O 0.8441(6) 0.1543(5) 0.5638(5) 0.0322(12) Uani 1 1 d . . . . .
O8 O 0.8490(6) -0.0673(5) 0.5709(6) 0.0349(13) Uani 1 1 d . . . . .
O9 O 0.6644(6) -0.1422(5) 0.6144(4) 0.0276(10) Uani 1 1 d . . . . .
C33 C 0.0349(8) 0.2893(7) 0.7633(6) 0.0251(13) Uani 1 1 d . . . . .
C34 C 0.1518(9) 0.3267(8) 0.7071(6) 0.0299(16) Uani 1 1 d . . . . .
C35 C 0.2862(8) 0.2551(7) 0.6940(6) 0.0256(14) Uani 1 1 d . . . . .
C36 C 0.3081(7) 0.1392(7) 0.7392(6) 0.0243(13) Uani 1 1 d . . . . .
C37 C 0.1896(8) 0.1001(6) 0.7969(6) 0.0255(13) Uani 1 1 d . . . . .
C38 C 0.0552(8) 0.1738(7) 0.8077(5) 0.0258(13) Uani 1 1 d . . . . .
C39 C 0.4842(8) -0.0316(6) 0.7137(6) 0.0263(13) Uani 1 1 d . . . . .
H39A H 0.402789 -0.045563 0.704153 0.032 Uiso 1 1 calc R . . . .
H39B H 0.516319 -0.090822 0.774124 0.032 Uiso 1 1 calc R . . . .
C40 C 0.6034(7) -0.0302(6) 0.6172(5) 0.0227(11) Uani 1 1 d . . . . .
H40 H 0.567102 0.017512 0.553622 0.027 Uiso 1 1 calc R . . . .
C41 C 0.7289(7) 0.0032(6) 0.6202(5) 0.0235(12) Uani 1 1 d . . . . .
H41 H 0.732095 -0.011732 0.693398 0.028 Uiso 1 1 calc R . . . .
C42 C 0.7253(7) 0.1238(6) 0.5602(6) 0.0311(14) Uani 1 1 d . . . . .
H42A H 0.727115 0.135991 0.487150 0.037 Uiso 1 1 calc R . . . .
H42B H 0.635871 0.172804 0.589507 0.037 Uiso 1 1 calc R . . . .
C43 C 0.9737(7) 0.1074(6) 0.5103(6) 0.0248(13) Uani 1 1 d . . . . .
C44 C 1.0073(8) 0.1208(7) 0.4047(6) 0.0267(14) Uani 1 1 d . . . . .
C45 C 1.1413(8) 0.0726(6) 0.3540(6) 0.0244(13) Uani 1 1 d . . . . .
C46 C 1.2494(7) 0.0109(6) 0.4049(6) 0.0210(12) Uani 1 1 d . . . . .
C47 C 1.2173(7) 0.0026(6) 0.5092(6) 0.0251(13) Uani 1 1 d . . . . .
C48 C 1.0841(8) 0.0497(6) 0.5606(6) 0.0256(13) Uani 1 1 d . . . . .
C49 C 0.8068(8) -0.1490(6) 0.5544(6) 0.0251(13) Uani 1 1 d . . . . .
C50 C 0.8995(9) -0.2637(7) 0.5963(7) 0.0345(16) Uani 1 1 d . . . . .
H50A H 0.863640 -0.321415 0.593201 0.041 Uiso 1 1 calc R . . . .
H50B H 0.896502 -0.275965 0.669575 0.041 Uiso 1 1 calc R . . . .
C51 C 1.0538(9) -0.2740(8) 0.5317(8) 0.041(2) Uani 1 1 d . . . . .
H51A H 1.092603 -0.221248 0.540371 0.049 Uiso 1 1 calc R . . . .
H51B H 1.112658 -0.350607 0.556963 0.049 Uiso 1 1 calc R . . . .
C52 C 1.0601(10) -0.2489(8) 0.4181(9) 0.045(2) Uani 1 1 d . . . . .
H52A H 1.029043 -0.305838 0.408995 0.054 Uiso 1 1 calc R . . . .
H52B H 1.159119 -0.253486 0.378085 0.054 Uiso 1 1 calc R . . . .
C53 C 0.9664(10) -0.1330(8) 0.3759(7) 0.0392(19) Uani 1 1 d . . . . .
H53A H 1.002730 -0.075399 0.378792 0.047 Uiso 1 1 calc R . . . .
H53B H 0.969539 -0.120821 0.302618 0.047 Uiso 1 1 calc R . . . .
C54 C 0.8138(9) -0.1214(8) 0.4391(7) 0.0327(17) Uani 1 1 d . . . . .
H54A H 0.773546 -0.172456 0.429086 0.039 Uiso 1 1 calc R . . . .
H54B H 0.756407 -0.044042 0.414311 0.039 Uiso 1 1 calc R . . . .
N1 N -0.6571(7) 0.6577(6) 0.6815(6) 0.0318(14) Uani 1 1 d . . . . .
N2 N -0.7419(7) 0.6017(7) 0.7378(5) 0.0314(14) Uani 1 1 d . . . . .
N3 N -0.2635(8) 0.4899(7) 0.5300(6) 0.0327(15) Uani 1 1 d . . . . .
N4 N -1.1277(8) 0.7731(7) 0.8964(6) 0.0377(17) Uani 1 1 d . . . . .
C23 C -0.5248(8) 0.5941(8) 0.6329(6) 0.0289(15) Uani 1 1 d . . . . .
C24 C -0.4868(9) 0.4786(7) 0.6525(7) 0.0300(16) Uani 1 1 d . . . . .
H24 H -0.548654 0.434612 0.699910 0.036 Uiso 1 1 calc R . . . .
C25 C -0.3537(8) 0.4312(8) 0.5992(7) 0.0335(16) Uani 1 1 d . . . . .
H25 H -0.324628 0.352396 0.612474 0.040 Uiso 1 1 calc R . . . .
C26 C -0.3020(9) 0.5987(8) 0.5146(7) 0.0340(17) Uani 1 1 d . . . . .
H26 H -0.237720 0.640578 0.467315 0.041 Uiso 1 1 calc R . . . .
C27 C -0.4315(10) 0.6550(8) 0.5638(7) 0.0351(17) Uani 1 1 d . . . . .
H27 H -0.455567 0.733720 0.550381 0.042 Uiso 1 1 calc R . . . .
C28 C -0.8714(8) 0.6653(7) 0.7887(6) 0.0273(14) Uani 1 1 d . . . . .
C29 C -0.8989(8) 0.7763(7) 0.7806(6) 0.0323(16) Uani 1 1 d . . . . .
H29 H -0.831332 0.817400 0.739297 0.039 Uiso 1 1 calc R . . . .
C30 C -1.0298(9) 0.8258(8) 0.8355(7) 0.0365(18) Uani 1 1 d . . . . .
H30 H -1.050345 0.902922 0.828848 0.044 Uiso 1 1 calc R . . . .
C31 C -1.0977(9) 0.6639(8) 0.9034(7) 0.0365(18) Uani 1 1 d . . . . .
H31 H -1.166070 0.624210 0.946507 0.044 Uiso 1 1 calc R . . . .
C32 C -0.9713(9) 0.6072(8) 0.8503(6) 0.0324(16) Uani 1 1 d . . . . .
H32 H -0.954021 0.530678 0.856175 0.039 Uiso 1 1 calc R . . . .
N5 N -0.8129(7) 0.7170(6) 1.0158(6) 0.0291(13) Uani 1 1 d . . . . .
N6 N -0.9018(7) 0.6637(6) 1.0645(6) 0.0325(14) Uani 1 1 d . . . . .
N7 N -0.4327(7) 0.5456(7) 0.8521(6) 0.0323(15) Uani 1 1 d . . . . .
N8 N -1.2824(7) 0.8357(6) 1.2260(6) 0.0311(14) Uani 1 1 d . . . . .
C55 C -0.6847(8) 0.6524(7) 0.9618(6) 0.0298(15) Uani 1 1 d . . . . .
C56 C -0.6630(8) 0.5443(7) 0.9630(6) 0.0295(15) Uani 1 1 d . . . . .
H56 H -0.733737 0.505421 1.000746 0.035 Uiso 1 1 calc R . . . .
C57 C -0.5344(8) 0.4944(7) 0.9073(6) 0.0299(15) Uani 1 1 d . . . . .
H57 H -0.517908 0.419412 0.908602 0.036 Uiso 1 1 calc R . . . .
C58 C -0.4551(9) 0.6506(9) 0.8508(8) 0.041(2) Uani 1 1 d . . . . .
H58 H -0.382910 0.687602 0.811340 0.049 Uiso 1 1 calc R . . . .
C59 C -0.5801(10) 0.7082(8) 0.9049(8) 0.0369(18) Uani 1 1 d . . . . .
H59 H -0.593465 0.782889 0.903010 0.044 Uiso 1 1 calc R . . . .
C60 C -1.0295(8) 0.7262(7) 1.1181(7) 0.0284(14) Uani 1 1 d . . . . .
C61 C -1.1268(9) 0.6669(7) 1.1842(7) 0.0338(17) Uani 1 1 d . . . . .
H61 H -1.109684 0.589811 1.192634 0.041 Uiso 1 1 calc R . . . .
C62 C -1.2523(9) 0.7266(8) 1.2383(7) 0.0337(17) Uani 1 1 d . . . . .
H62 H -1.318965 0.687157 1.285969 0.040 Uiso 1 1 calc R . . . .
C63 C -1.1888(9) 0.8905(7) 1.1612(8) 0.0350(17) Uani 1 1 d . . . . .
H63 H -1.210488 0.968185 1.152327 0.042 Uiso 1 1 calc R . . . .
C64 C -1.0608(9) 0.8399(8) 1.1057(8) 0.0346(18) Uani 1 1 d . . . . .
H64 H -0.995635 0.881797 1.060166 0.041 Uiso 1 1 calc R . . . .


_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
I1 C1 2.097(7) . ?
I2 C14 2.108(7) . ?
F6 C13 1.344(9) . ?
F5 C12 1.339(9) . ?
F8 C16 1.341(9) . ?
F7 C15 1.349(10) . ?
F1 C2 1.341(7) . ?
F2 C3 1.350(7) . ?
F4 C6 1.348(8) . ?
F3 C5 1.348(8) . ?
O1 C10 1.443(9) . ?
O1 C11 1.361(8) . ?
O2 C9 1.428(8) . ?
O2 C17 1.441(9) . ?
O3 C8 1.423(8) . ?
O3 C17 1.412(9) . ?
O7 C4 1.365(8) . ?
O7 C7 1.454(8) . ?
C1 C2 1.386(10) . ?
C1 C6 1.401(10) . ?
C2 C3 1.385(10) . ?
C3 C4 1.389(9) . ?
C4 C5 1.387(10) . ?
C5 C6 1.365(11) . ?
C7 C8 1.513(10) . ?
C8 C9 1.541(9) . ?
C9 C10 1.508(9) . ?
C11 C12 1.392(10) . ?
C11 C16 1.386(11) . ?
C12 C13 1.397(10) . ?
C13 C14 1.358(12) . ?
C14 C15 1.396(11) . ?
C15 C16 1.380(11) . ?
C17 C18 1.529(11) . ?
C17 C22 1.530(10) . ?
C18 C19 1.525(11) . ?
C19 C20 1.517(14) . ?
C20 C21 1.518(15) . ?
C21 C22 1.533(12) . ?
I3 C33 2.086(7) . ?
I4 C46 2.100(7) . ?
F12 C38 1.339(8) . ?
F11 C37 1.338(9) . ?
F9 C34 1.331(11) . ?
F10 C35 1.340(8) . ?
F15 C47 1.351(8) . ?
F16 C48 1.345(8) . ?
F13 C44 1.347(8) . ?
F14 C45 1.345(8) . ?
O4 C36 1.352(9) . ?
O4 C39 1.455(9) . ?
O5 C42 1.454(9) . ?
O5 C43 1.365(9) . ?
O8 C41 1.419(9) . ?
O8 C49 1.431(9) . ?
O9 C40 1.414(9) . ?
O9 C49 1.432(9) . ?
C33 C34 1.363(11) . ?
C33 C38 1.401(11) . ?
C34 C35 1.382(11) . ?
C35 C36 1.407(11) . ?
C36 C37 1.391(10) . ?
C37 C38 1.391(10) . ?
C39 C40 1.516(9) . ?
C40 C41 1.541(9) . ?
C41 C42 1.514(10) . ?
C43 C44 1.387(11) . ?
C43 C48 1.392(10) . ?
C44 C45 1.385(11) . ?
C45 C46 1.382(9) . ?
C46 C47 1.385(10) . ?
C47 C48 1.378(10) . ?
C49 C50 1.513(11) . ?
C49 C54 1.532(11) . ?
C50 C51 1.548(12) . ?
C51 C52 1.513(16) . ?
C52 C53 1.530(13) . ?
C53 C54 1.527(13) . ?
N1 N2 1.240(11) . ?
N1 C23 1.439(10) . ?
N2 C28 1.435(10) . ?
N3 C25 1.343(12) . ?
N3 C26 1.316(12) . ?
N4 C30 1.326(12) . ?
N4 C31 1.353(13) . ?
C23 C24 1.392(12) . ?
C23 C27 1.382(12) . ?
C24 C25 1.390(11) . ?
C26 C27 1.385(12) . ?
C28 C29 1.376(12) . ?
C28 C32 1.385(12) . ?
C29 C30 1.394(12) . ?
C31 C32 1.390(12) . ?
N5 N6 1.233(10) . ?
N5 C55 1.453(10) . ?
N6 C60 1.434(10) . ?
N7 C57 1.331(11) . ?
N7 C58 1.334(13) . ?
N8 C62 1.334(12) . ?
N8 C63 1.322(12) . ?
C55 C56 1.377(12) . ?
C55 C59 1.393(12) . ?
C56 C57 1.386(10) . ?
C58 C59 1.394(13) . ?
C60 C61 1.387(11) . ?
C60 C64 1.393(12) . ?
C61 C62 1.408(11) . ?
C63 C64 1.384(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C10 115.4(5) . . ?
C9 O2 C17 108.4(5) . . ?
C17 O3 C8 107.3(5) . . ?
C4 O7 C7 115.0(5) . . ?
C2 C1 I1 121.1(5) . . ?
C2 C1 C6 116.2(6) . . ?
C6 C1 I1 122.7(5) . . ?
F1 C2 C1 120.2(6) . . ?
F1 C2 C3 118.0(6) . . ?
C3 C2 C1 121.8(6) . . ?
F2 C3 C2 119.4(6) . . ?
F2 C3 C4 119.2(6) . . ?
C2 C3 C4 121.4(6) . . ?
O7 C4 C3 122.6(6) . . ?
O7 C4 C5 120.7(6) . . ?
C5 C4 C3 116.7(6) . . ?
F3 C5 C4 118.9(7) . . ?
F3 C5 C6 119.2(7) . . ?
C6 C5 C4 121.8(7) . . ?
F4 C6 C1 119.8(7) . . ?
F4 C6 C5 118.2(7) . . ?
C5 C6 C1 121.9(7) . . ?
O7 C7 C8 111.4(5) . . ?
O3 C8 C7 107.9(5) . . ?
O3 C8 C9 101.2(5) . . ?
C7 C8 C9 115.3(5) . . ?
O2 C9 C8 103.2(5) . . ?
O2 C9 C10 108.1(6) . . ?
C10 C9 C8 115.0(6) . . ?
O1 C10 C9 105.1(5) . . ?
O1 C11 C12 122.9(7) . . ?
O1 C11 C16 119.1(7) . . ?
C16 C11 C12 117.9(7) . . ?
F5 C12 C11 119.7(7) . . ?
F5 C12 C13 119.9(7) . . ?
C11 C12 C13 120.4(7) . . ?
F6 C13 C12 116.7(7) . . ?
F6 C13 C14 121.7(7) . . ?
C14 C13 C12 121.6(7) . . ?
C13 C14 I2 121.3(5) . . ?
C13 C14 C15 118.1(7) . . ?
C15 C14 I2 120.5(6) . . ?
F7 C15 C14 120.3(7) . . ?
F7 C15 C16 118.6(7) . . ?
C16 C15 C14 121.1(8) . . ?
F8 C16 C11 119.4(7) . . ?
F8 C16 C15 119.7(7) . . ?
C15 C16 C11 120.9(7) . . ?
O2 C17 C18 109.4(6) . . ?
O2 C17 C22 109.8(6) . . ?
O3 C17 O2 106.3(5) . . ?
O3 C17 C18 111.6(6) . . ?
O3 C17 C22 108.0(6) . . ?
C18 C17 C22 111.7(6) . . ?
C19 C18 C17 110.3(6) . . ?
C20 C19 C18 112.0(7) . . ?
C19 C20 C21 111.9(7) . . ?
C20 C21 C22 110.9(8) . . ?
C17 C22 C21 110.5(7) . . ?
C36 O4 C39 119.8(6) . . ?
C43 O5 C42 116.0(6) . . ?
C41 O8 C49 109.7(6) . . ?
C40 O9 C49 106.5(5) . . ?
C34 C33 I3 121.1(6) . . ?
C34 C33 C38 117.4(7) . . ?
C38 C33 I3 121.4(5) . . ?
F9 C34 C33 120.8(8) . . ?
F9 C34 C35 116.9(8) . . ?
C33 C34 C35 122.3(8) . . ?
F10 C35 C34 120.2(8) . . ?
F10 C35 C36 118.9(7) . . ?
C34 C35 C36 120.8(7) . . ?
O4 C36 C35 116.0(6) . . ?
O4 C36 C37 126.4(7) . . ?
C37 C36 C35 117.4(7) . . ?
F11 C37 C36 120.0(7) . . ?
F11 C37 C38 119.4(7) . . ?
C36 C37 C38 120.6(7) . . ?
F12 C38 C33 121.7(7) . . ?
F12 C38 C37 116.7(7) . . ?
C37 C38 C33 121.5(7) . . ?
O4 C39 C40 106.3(6) . . ?
O9 C40 C39 106.7(5) . . ?
O9 C40 C41 102.7(5) . . ?
C39 C40 C41 114.3(6) . . ?
O8 C41 C40 103.7(6) . . ?
O8 C41 C42 109.2(6) . . ?
C42 C41 C40 112.5(6) . . ?
O5 C42 C41 111.9(6) . . ?
O5 C43 C44 123.9(7) . . ?
O5 C43 C48 119.5(7) . . ?
C44 C43 C48 116.3(6) . . ?
F13 C44 C43 120.1(7) . . ?
F13 C44 C45 118.4(7) . . ?
C45 C44 C43 121.5(7) . . ?
F14 C45 C44 117.7(6) . . ?
F14 C45 C46 120.2(7) . . ?
C46 C45 C44 122.1(7) . . ?
C45 C46 I4 121.6(5) . . ?
C45 C46 C47 116.2(6) . . ?
C47 C46 I4 122.2(5) . . ?
F15 C47 C46 119.9(6) . . ?
F15 C47 C48 117.8(7) . . ?
C48 C47 C46 122.2(6) . . ?
F16 C48 C43 119.3(7) . . ?
F16 C48 C47 119.1(7) . . ?
C47 C48 C43 121.5(7) . . ?
O8 C49 O9 105.4(6) . . ?
O8 C49 C50 109.1(6) . . ?
O8 C49 C54 109.8(7) . . ?
O9 C49 C50 108.9(6) . . ?
O9 C49 C54 111.0(6) . . ?
C50 C49 C54 112.5(7) . . ?
C49 C50 C51 110.0(7) . . ?
C52 C51 C50 110.7(8) . . ?
C51 C52 C53 111.7(8) . . ?
C54 C53 C52 110.6(8) . . ?
C53 C54 C49 110.8(7) . . ?
N2 N1 C23 113.9(7) . . ?
N1 N2 C28 113.3(7) . . ?
C26 N3 C25 117.8(7) . . ?
C30 N4 C31 116.8(8) . . ?
C24 C23 N1 124.5(7) . . ?
C27 C23 N1 115.5(8) . . ?
C27 C23 C24 119.9(8) . . ?
C25 C24 C23 116.5(8) . . ?
N3 C25 C24 124.1(9) . . ?
N3 C26 C27 123.3(8) . . ?
C23 C27 C26 118.4(9) . . ?
C29 C28 N2 124.3(8) . . ?
C29 C28 C32 120.1(7) . . ?
C32 C28 N2 115.6(7) . . ?
C28 C29 C30 117.3(8) . . ?
N4 C30 C29 124.7(9) . . ?
N4 C31 C32 123.1(8) . . ?
C28 C32 C31 118.1(8) . . ?
N6 N5 C55 112.3(7) . . ?
N5 N6 C60 113.2(7) . . ?
C57 N7 C58 118.3(7) . . ?
C63 N8 C62 118.5(7) . . ?
C56 C55 N5 124.7(7) . . ?
C56 C55 C59 120.1(8) . . ?
C59 C55 N5 115.1(8) . . ?
C55 C56 C57 117.6(7) . . ?
N7 C57 C56 123.6(8) . . ?
N7 C58 C59 122.7(9) . . ?
C55 C59 C58 117.6(9) . . ?
C61 C60 N6 116.0(7) . . ?
C61 C60 C64 119.8(7) . . ?
C64 C60 N6 124.3(7) . . ?
C60 C61 C62 116.8(8) . . ?
N8 C62 C61 123.4(8) . . ?
N8 C63 C64 123.0(8) . . ?
C63 C64 C60 118.5(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 F1 0.3(10) . . . . ?
I1 C1 C2 C3 -179.3(5) . . . . ?
I1 C1 C6 F4 -0.8(10) . . . . ?
I1 C1 C6 C5 -178.2(6) . . . . ?
I2 C14 C15 F7 4.1(10) . . . . ?
I2 C14 C15 C16 -174.3(6) . . . . ?
F6 C13 C14 I2 -5.5(10) . . . . ?
F6 C13 C14 C15 179.3(7) . . . . ?
F5 C12 C13 F6 1.1(10) . . . . ?
F5 C12 C13 C14 -179.0(7) . . . . ?
F7 C15 C16 F8 0.8(12) . . . . ?
F7 C15 C16 C11 -179.0(7) . . . . ?
F1 C2 C3 F2 -1.4(10) . . . . ?
F1 C2 C3 C4 178.4(6) . . . . ?
F2 C3 C4 O7 1.4(10) . . . . ?
F2 C3 C4 C5 -177.6(6) . . . . ?
F3 C5 C6 F4 -2.4(11) . . . . ?
F3 C5 C6 C1 175.0(7) . . . . ?
O1 C11 C12 F5 3.8(10) . . . . ?
O1 C11 C12 C13 -175.1(6) . . . . ?
O1 C11 C16 F8 -4.2(10) . . . . ?
O1 C11 C16 C15 175.6(7) . . . . ?
O2 C9 C10 O1 -171.6(5) . . . . ?
O2 C17 C18 C19 177.3(6) . . . . ?
O2 C17 C22 C21 -178.0(7) . . . . ?
O3 C8 C9 O2 33.1(6) . . . . ?
O3 C8 C9 C10 150.6(6) . . . . ?
O3 C17 C18 C19 -65.3(8) . . . . ?
O3 C17 C22 C21 66.5(8) . . . . ?
O7 C4 C5 F3 2.7(10) . . . . ?
O7 C4 C5 C6 -179.0(7) . . . . ?
O7 C7 C8 O3 -73.7(7) . . . . ?
O7 C7 C8 C9 174.1(5) . . . . ?
C1 C2 C3 F2 178.2(7) . . . . ?
C1 C2 C3 C4 -2.0(11) . . . . ?
C2 C1 C6 F4 -178.9(7) . . . . ?
C2 C1 C6 C5 3.8(11) . . . . ?
C2 C3 C4 O7 -178.4(6) . . . . ?
C2 C3 C4 C5 2.5(10) . . . . ?
C3 C4 C5 F3 -178.2(6) . . . . ?
C3 C4 C5 C6 0.1(11) . . . . ?
C4 O7 C7 C8 64.9(7) . . . . ?
C4 C5 C6 F4 179.4(7) . . . . ?
C4 C5 C6 C1 -3.3(12) . . . . ?
C6 C1 C2 F1 178.4(6) . . . . ?
C6 C1 C2 C3 -1.2(11) . . . . ?
C7 O7 C4 C3 72.1(8) . . . . ?
C7 O7 C4 C5 -108.9(7) . . . . ?
C7 C8 C9 O2 149.1(6) . . . . ?
C7 C8 C9 C10 -93.3(7) . . . . ?
C8 O3 C17 O2 26.7(7) . . . . ?
C8 O3 C17 C18 -92.5(7) . . . . ?
C8 O3 C17 C22 144.5(6) . . . . ?
C8 C9 C10 O1 73.7(7) . . . . ?
C9 O2 C17 O3 -3.9(7) . . . . ?
C9 O2 C17 C18 116.7(6) . . . . ?
C9 O2 C17 C22 -120.4(7) . . . . ?
C10 O1 C11 C12 -73.4(9) . . . . ?
C10 O1 C11 C16 111.0(8) . . . . ?
C11 O1 C10 C9 -169.4(6) . . . . ?
C11 C12 C13 F6 180.0(6) . . . . ?
C11 C12 C13 C14 -0.1(11) . . . . ?
C12 C11 C16 F8 180.0(6) . . . . ?
C12 C11 C16 C15 -0.2(11) . . . . ?
C12 C13 C14 I2 174.5(5) . . . . ?
C12 C13 C14 C15 -0.7(11) . . . . ?
C13 C14 C15 F7 179.4(7) . . . . ?
C13 C14 C15 C16 1.0(12) . . . . ?
C14 C15 C16 F8 179.3(7) . . . . ?
C14 C15 C16 C11 -0.5(12) . . . . ?
C16 C11 C12 F5 179.4(7) . . . . ?
C16 C11 C12 C13 0.5(10) . . . . ?
C17 O2 C9 C8 -18.1(7) . . . . ?
C17 O2 C9 C10 -140.4(6) . . . . ?
C17 O3 C8 C7 -158.2(6) . . . . ?
C17 O3 C8 C9 -36.7(7) . . . . ?
C17 C18 C19 C20 -54.6(10) . . . . ?
C18 C17 C22 C21 -56.5(9) . . . . ?
C18 C19 C20 C21 55.1(11) . . . . ?
C19 C20 C21 C22 -55.3(11) . . . . ?
C20 C21 C22 C17 55.7(10) . . . . ?
C22 C17 C18 C19 55.6(9) . . . . ?
I3 C33 C34 F9 -4.1(11) . . . . ?
I3 C33 C34 C35 176.0(6) . . . . ?
I3 C33 C38 F12 1.4(10) . . . . ?
I3 C33 C38 C37 -175.1(5) . . . . ?
I4 C46 C47 F15 2.1(10) . . . . ?
I4 C46 C47 C48 -177.7(6) . . . . ?
F11 C37 C38 F12 -0.6(10) . . . . ?
F11 C37 C38 C33 176.0(7) . . . . ?
F9 C34 C35 F10 0.4(11) . . . . ?
F9 C34 C35 C36 179.8(7) . . . . ?
F10 C35 C36 O4 5.1(10) . . . . ?
F10 C35 C36 C37 179.5(6) . . . . ?
F15 C47 C48 F16 -0.1(11) . . . . ?
F15 C47 C48 C43 -179.0(7) . . . . ?
F13 C44 C45 F14 -0.3(11) . . . . ?
F13 C44 C45 C46 179.1(7) . . . . ?
F14 C45 C46 I4 -2.5(10) . . . . ?
F14 C45 C46 C47 177.6(7) . . . . ?
O4 C36 C37 F11 -3.0(11) . . . . ?
O4 C36 C37 C38 174.5(7) . . . . ?
O4 C39 C40 O9 166.8(5) . . . . ?
O4 C39 C40 C41 54.0(8) . . . . ?
O5 C43 C44 F13 -1.5(12) . . . . ?
O5 C43 C44 C45 179.0(7) . . . . ?
O5 C43 C48 F16 2.2(11) . . . . ?
O5 C43 C48 C47 -178.9(7) . . . . ?
O8 C41 C42 O5 -65.6(8) . . . . ?
O8 C49 C50 C51 -66.3(9) . . . . ?
O8 C49 C54 C53 66.0(9) . . . . ?
O9 C40 C41 O8 26.7(7) . . . . ?
O9 C40 C41 C42 144.5(6) . . . . ?
O9 C49 C50 C51 179.1(7) . . . . ?
O9 C49 C54 C53 -177.9(7) . . . . ?
C33 C34 C35 F10 -179.7(7) . . . . ?
C33 C34 C35 C36 -0.3(12) . . . . ?
C34 C33 C38 F12 177.8(7) . . . . ?
C34 C33 C38 C37 1.3(11) . . . . ?
C34 C35 C36 O4 -174.2(7) . . . . ?
C34 C35 C36 C37 0.2(11) . . . . ?
C35 C36 C37 F11 -176.8(7) . . . . ?
C35 C36 C37 C38 0.7(11) . . . . ?
C36 O4 C39 C40 126.2(7) . . . . ?
C36 C37 C38 F12 -178.2(7) . . . . ?
C36 C37 C38 C33 -1.5(11) . . . . ?
C38 C33 C34 F9 179.5(7) . . . . ?
C38 C33 C34 C35 -0.4(12) . . . . ?
C39 O4 C36 C35 -143.2(7) . . . . ?
C39 O4 C36 C37 43.0(11) . . . . ?
C39 C40 C41 O8 141.9(6) . . . . ?
C39 C40 C41 C42 -100.3(7) . . . . ?
C40 O9 C49 O8 30.4(7) . . . . ?
C40 O9 C49 C50 147.3(6) . . . . ?
C40 O9 C49 C54 -88.4(7) . . . . ?
C40 C41 C42 O5 179.9(6) . . . . ?
C41 O8 C49 O9 -12.2(8) . . . . ?
C41 O8 C49 C50 -129.0(7) . . . . ?
C41 O8 C49 C54 107.4(7) . . . . ?
C42 O5 C43 C44 58.9(10) . . . . ?
C42 O5 C43 C48 -126.5(7) . . . . ?
C43 O5 C42 C41 69.7(9) . . . . ?
C43 C44 C45 F14 179.1(7) . . . . ?
C43 C44 C45 C46 -1.4(12) . . . . ?
C44 C43 C48 F16 177.2(7) . . . . ?
C44 C43 C48 C47 -3.9(11) . . . . ?
C44 C45 C46 I4 178.0(6) . . . . ?
C44 C45 C46 C47 -1.8(11) . . . . ?
C45 C46 C47 F15 -178.1(7) . . . . ?
C45 C46 C47 C48 2.2(11) . . . . ?
C46 C47 C48 F16 179.6(7) . . . . ?
C46 C47 C48 C43 0.7(12) . . . . ?
C48 C43 C44 F13 -176.4(7) . . . . ?
C48 C43 C44 C45 4.2(11) . . . . ?
C49 O8 C41 C40 -8.8(8) . . . . ?
C49 O8 C41 C42 -128.9(7) . . . . ?
C49 O9 C40 C39 -155.5(6) . . . . ?
C49 O9 C40 C41 -35.0(6) . . . . ?
C49 C50 C51 C52 -56.0(10) . . . . ?
C50 C49 C54 C53 -55.6(10) . . . . ?
C50 C51 C52 C53 57.0(11) . . . . ?
C51 C52 C53 C54 -56.5(11) . . . . ?
C52 C53 C54 C49 54.6(11) . . . . ?
C54 C49 C50 C51 55.7(9) . . . . ?
N1 N2 C28 C29 -2.6(11) . . . . ?
N1 N2 C28 C32 178.3(7) . . . . ?
N1 C23 C24 C25 -179.2(8) . . . . ?
N1 C23 C27 C26 179.8(8) . . . . ?
N2 N1 C23 C24 -5.6(12) . . . . ?
N2 N1 C23 C27 175.5(7) . . . . ?
N2 C28 C29 C30 -179.6(8) . . . . ?
N2 C28 C32 C31 178.6(8) . . . . ?
N3 C26 C27 C23 0.3(14) . . . . ?
N4 C31 C32 C28 0.8(14) . . . . ?
C23 N1 N2 C28 177.9(7) . . . . ?
C23 C24 C25 N3 -1.3(13) . . . . ?
C24 C23 C27 C26 0.9(13) . . . . ?
C25 N3 C26 C27 -1.8(13) . . . . ?
C26 N3 C25 C24 2.4(13) . . . . ?
C27 C23 C24 C25 -0.3(12) . . . . ?
C28 C29 C30 N4 1.6(14) . . . . ?
C29 C28 C32 C31 -0.5(12) . . . . ?
C30 N4 C31 C32 0.0(14) . . . . ?
C31 N4 C30 C29 -1.3(14) . . . . ?
C32 C28 C29 C30 -0.6(12) . . . . ?
N5 N6 C60 C61 -172.5(8) . . . . ?
N5 N6 C60 C64 8.9(12) . . . . ?
N5 C55 C56 C57 -180.0(7) . . . . ?
N5 C55 C59 C58 -179.5(8) . . . . ?
N6 N5 C55 C56 0.5(12) . . . . ?
N6 N5 C55 C59 179.8(8) . . . . ?
N6 C60 C61 C62 179.4(8) . . . . ?
N6 C60 C64 C63 179.2(9) . . . . ?
N7 C58 C59 C55 -0.3(15) . . . . ?
N8 C63 C64 C60 0.5(15) . . . . ?
C55 N5 N6 C60 -179.8(7) . . . . ?
C55 C56 C57 N7 -1.0(12) . . . . ?
C56 C55 C59 C58 -0.2(14) . . . . ?
C57 N7 C58 C59 0.1(15) . . . . ?
C58 N7 C57 C56 0.5(13) . . . . ?
C59 C55 C56 C57 0.8(12) . . . . ?
C60 C61 C62 N8 2.3(14) . . . . ?
C61 C60 C64 C63 0.7(14) . . . . ?
C62 N8 C63 C64 -0.2(14) . . . . ?
C63 N8 C62 C61 -1.2(14) . . . . ?
C64 C60 C61 C62 -1.9(13) . . . . ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 / heptane'
####################################################################### 
# 
# 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_apy_3
_database_code_depnum_ccdc_archive 'CCDC 1868143'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2018-09-17 deposited with the CCDC.	2019-03-12 downloaded from the CCDC.
;
_audit_creation_date             2018-08-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H12 F8 I2 O2, C10 H8 N4'
_chemical_formula_sum            'C42 H20 F8 I2 N4 O2'
_chemical_formula_weight         1018.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.5438(5)
_cell_length_b                   14.8242(7)
_cell_length_c                   21.8290(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3735.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    58389
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.5523
_exptl_absorpt_correction_T_max  0.8308
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -4 0.1270
1 0 4 0.1440
1 2 3 0.1330
0 -3 -1 0.1800
0 1 0 0.2000
1 0 -2 0.0440
-3 -2 -2 0.1230
-2 -1 3 0.0840
-2 1 5 0.0890
-3 1 4 0.0830
0 -3 4 0.2050

_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            54653
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.282
_diffrn_reflns_theta_min         2.236
_diffrn_ambient_temperature      120
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                8360
_reflns_number_total             10101
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        'STOE X-Area'

_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.961
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 
;
 Flack x determined using 3261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.030(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         10101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0734P)²+2.0256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1234
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C25(H25),
 C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C34(H34), C35(H35), C36(H36),
  C37(H37), C39(H39), C40(H40), C41(H41), C42(H42)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
I1 I -0.19490(4) 0.28021(3) 0.14097(2) 0.04082(12) Uani 1 1 d . . . . .
I2 I 0.78041(4) -0.15959(4) 0.06938(2) 0.05196(15) Uani 1 1 d . . . . .
F1 F -0.0738(4) 0.1657(3) 0.03667(17) 0.0455(10) Uani 1 1 d . . . . .
F2 F 0.0663(4) 0.0218(3) 0.03886(19) 0.0457(10) Uani 1 1 d . . . . .
F3 F -0.0933(4) 0.1580(3) 0.25316(18) 0.0448(9) Uani 1 1 d . . . . .
F4 F 0.0510(4) 0.0163(3) 0.25436(19) 0.0440(10) Uani 1 1 d . . . . .
F5 F 0.7272(4) 0.0529(3) 0.0546(2) 0.0544(11) Uani 1 1 d . . . . .
F6 F 0.5302(4) 0.1447(3) 0.0389(2) 0.0482(10) Uani 1 1 d . . . . .
F7 F 0.5147(5) -0.2190(3) 0.0627(2) 0.0567(11) Uani 1 1 d . . . . .
F8 F 0.3188(4) -0.1262(3) 0.0436(2) 0.0517(11) Uani 1 1 d . . . . .
O1 O 0.1370(4) -0.0549(3) 0.1455(3) 0.0408(10) Uani 1 1 d . . . . .
O2 O 0.3185(4) 0.0554(4) 0.0313(2) 0.0434(12) Uani 1 1 d . . . . .
C1 C -0.0857(5) 0.1666(5) 0.1447(3) 0.0378(13) Uani 1 1 d . . . . .
C2 C -0.0442(6) 0.1297(5) 0.0911(3) 0.0392(15) Uani 1 1 d . . . . .
C3 C 0.0278(6) 0.0564(5) 0.0920(3) 0.0367(14) Uani 1 1 d . . . . .
C4 C 0.0645(6) 0.0184(5) 0.1468(3) 0.0373(13) Uani 1 1 d . . . . .
C5 C 0.0203(6) 0.0537(5) 0.2011(3) 0.0358(14) Uani 1 1 d . . . . .
C6 C -0.0540(6) 0.1274(5) 0.1992(3) 0.0376(14) Uani 1 1 d . . . . .
C7 C 0.6262(6) -0.0866(6) 0.0596(3) 0.0437(16) Uani 1 1 d . . . . .
C8 C 0.5227(7) -0.1285(5) 0.0562(3) 0.0438(16) Uani 1 1 d . . . . .
C9 C 0.4201(6) -0.0818(5) 0.0473(3) 0.0416(16) Uani 1 1 d . . . . .
C10 C 0.4207(6) 0.0111(5) 0.0425(3) 0.0390(15) Uani 1 1 d . . . . .
C11 C 0.5272(7) 0.0555(5) 0.0449(3) 0.0418(16) Uani 1 1 d . . . . .
C12 C 0.6278(6) 0.0074(5) 0.0530(3) 0.0418(16) Uani 1 1 d . . . . .
C13 C 0.2495(6) -0.0491(5) 0.1691(3) 0.0342(13) Uani 1 1 d . . . . .
C14 C 0.2870(7) -0.1322(4) 0.1949(3) 0.0383(14) Uani 1 1 d . . . . .
H14 H 0.235363 -0.181978 0.197211 0.046 Uiso 1 1 calc R . . . .
C15 C 0.3970(7) -0.1401(5) 0.2161(3) 0.0429(16) Uani 1 1 d . . . . .
H15 H 0.423042 -0.196299 0.231835 0.051 Uiso 1 1 calc R . . . .
C16 C 0.4730(6) -0.0659(5) 0.2151(3) 0.0376(14) Uani 1 1 d . . . . .
C17 C 0.5882(7) -0.0723(6) 0.2373(3) 0.0442(17) Uani 1 1 d . . . . .
H17 H 0.615894 -0.128619 0.252060 0.053 Uiso 1 1 calc R . . . .
C18 C 0.6607(7) 0.0015(6) 0.2378(3) 0.0480(18) Uani 1 1 d . . . . .
H18 H 0.737357 -0.003817 0.253184 0.058 Uiso 1 1 calc R . . . .
C19 C 0.6208(6) 0.0843(6) 0.2154(3) 0.0432(16) Uani 1 1 d . . . . .
H19 H 0.670171 0.135558 0.216404 0.052 Uiso 1 1 calc R . . . .
C20 C 0.5108(6) 0.0919(5) 0.1922(3) 0.0381(14) Uani 1 1 d . . . . .
H20 H 0.485948 0.148627 0.176690 0.046 Uiso 1 1 calc R . . . .
C21 C 0.4340(6) 0.0189(5) 0.1905(3) 0.0358(14) Uani 1 1 d . . . . .
C22 C 0.3196(6) 0.0253(5) 0.1649(3) 0.0335(13) Uani 1 1 d . . . . .
C23 C 0.2832(5) 0.1105(4) 0.1342(3) 0.0342(12) Uani 1 1 d . . . . .
C24 C 0.2846(6) 0.1225(5) 0.0721(3) 0.0373(13) Uani 1 1 d . . . . .
C25 C 0.2419(6) 0.2014(5) 0.0440(3) 0.0443(17) Uani 1 1 d . . . . .
H25 H 0.244852 0.207310 0.000720 0.053 Uiso 1 1 calc R . . . .
C26 C 0.1961(6) 0.2697(5) 0.0788(3) 0.0458(16) Uani 1 1 d . . . . .
H26 H 0.166395 0.322196 0.059411 0.055 Uiso 1 1 calc R . . . .
C27 C 0.1929(5) 0.2621(5) 0.1431(3) 0.0408(14) Uani 1 1 d . . . . .
C28 C 0.1407(7) 0.3280(5) 0.1807(4) 0.0486(18) Uani 1 1 d . . . . .
H28 H 0.109174 0.380546 0.162202 0.058 Uiso 1 1 calc R . . . .
C29 C 0.1340(7) 0.3189(5) 0.2416(4) 0.0506(19) Uani 1 1 d . . . . .
H29 H 0.096231 0.363775 0.265350 0.061 Uiso 1 1 calc R . . . .
C30 C 0.1826(7) 0.2429(5) 0.2705(3) 0.0448(16) Uani 1 1 d . . . . .
H30 H 0.179815 0.237431 0.313836 0.054 Uiso 1 1 calc R . . . .
C31 C 0.2340(6) 0.1770(5) 0.2361(3) 0.0391(14) Uani 1 1 d . . . . .
H31 H 0.267036 0.126046 0.255903 0.047 Uiso 1 1 calc R . . . .
C32 C 0.2387(6) 0.1834(4) 0.1713(3) 0.0343(13) Uani 1 1 d . . . . .
N1 N -0.6523(6) 0.5829(4) 0.1097(3) 0.0429(14) Uani 1 1 d . . . . .
N2 N -0.7489(5) 0.5461(4) 0.1035(3) 0.0405(13) Uani 1 1 d . . . . .
N3 N -0.3626(6) 0.4147(5) 0.1250(3) 0.0480(15) Uani 1 1 d . . . . .
N4 N -1.0294(6) 0.7241(6) 0.0853(3) 0.0539(17) Uani 1 1 d . . . . .
C33 C -0.5576(7) 0.5219(5) 0.1126(3) 0.0409(15) Uani 1 1 d . . . . .
C34 C -0.5640(7) 0.4313(5) 0.0965(3) 0.0443(17) Uani 1 1 d . . . . .
H34 H -0.633818 0.405034 0.081959 0.053 Uiso 1 1 calc R . . . .
C35 C -0.4644(7) 0.3817(6) 0.1027(4) 0.0504(19) Uani 1 1 d . . . . .
H35 H -0.466597 0.320129 0.090723 0.060 Uiso 1 1 calc R . . . .
C36 C -0.3623(7) 0.5006(6) 0.1411(4) 0.0511(18) Uani 1 1 d . . . . .
H36 H -0.292697 0.524276 0.157811 0.061 Uiso 1 1 calc R . . . .
C37 C -0.4543(7) 0.5580(6) 0.1355(4) 0.0502(18) Uani 1 1 d . . . . .
H37 H -0.448376 0.619696 0.146795 0.060 Uiso 1 1 calc R . . . .
C38 C -0.8419(7) 0.6090(5) 0.0982(3) 0.0382(14) Uani 1 1 d . . . . .
C39 C -0.8253(7) 0.7013(5) 0.0876(3) 0.0443(17) Uani 1 1 d . . . . .
H39 H -0.749708 0.726441 0.085224 0.053 Uiso 1 1 calc R . . . .
C40 C -0.9222(8) 0.7543(6) 0.0809(4) 0.052(2) Uani 1 1 d . . . . .
H40 H -0.911311 0.816567 0.072426 0.063 Uiso 1 1 calc R . . . .
C41 C -1.0434(8) 0.6358(6) 0.0962(4) 0.0496(19) Uani 1 1 d . . . . .
H41 H -1.120176 0.613440 0.100040 0.059 Uiso 1 1 calc R . . . .
C42 C -0.9532(7) 0.5756(6) 0.1020(3) 0.0454(18) Uani 1 1 d . . . . .
H42 H -0.967230 0.513186 0.108427 0.054 Uiso 1 1 calc R . . . .


_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
I1 C1 2.106(7) . ?
I2 C7 2.094(7) . ?
F1 C2 1.348(8) . ?
F2 C3 1.344(8) . ?
F3 C6 1.342(8) . ?
F4 C5 1.335(8) . ?
F5 C12 1.332(9) . ?
F6 C11 1.330(9) . ?
F7 C8 1.352(9) . ?
F8 C9 1.344(9) . ?
O1 C4 1.371(8) . ?
O1 C13 1.400(8) . ?
O2 C10 1.372(8) . ?
O2 C24 1.392(8) . ?
C1 C2 1.378(10) . ?
C1 C6 1.372(10) . ?
C2 C3 1.367(10) . ?
C3 C4 1.390(10) . ?
C4 C5 1.393(10) . ?
C5 C6 1.389(10) . ?
C7 C8 1.349(12) . ?
C7 C12 1.401(12) . ?
C8 C9 1.386(11) . ?
C9 C10 1.382(11) . ?
C10 C11 1.395(11) . ?
C11 C12 1.373(11) . ?
C13 C14 1.423(9) . ?
C13 C22 1.371(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.357(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.407(11) . ?
C16 C17 1.418(10) . ?
C16 C21 1.439(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.399(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.373(10) . ?
C20 H20 0.9500 . ?
C20 C21 1.400(10) . ?
C21 C22 1.436(9) . ?
C22 C23 1.491(9) . ?
C23 C24 1.367(9) . ?
C23 C32 1.445(9) . ?
C24 C25 1.409(10) . ?
C25 H25 0.9500 . ?
C25 C26 1.370(11) . ?
C26 H26 0.9500 . ?
C26 C27 1.409(10) . ?
C27 C28 1.411(11) . ?
C27 C32 1.422(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.338(12) . ?
C29 H29 0.9500 . ?
C29 C30 1.408(11) . ?
C30 H30 0.9500 . ?
C30 C31 1.368(10) . ?
C31 H31 0.9500 . ?
C31 C32 1.419(9) . ?
N1 N2 1.248(9) . ?
N1 C33 1.420(10) . ?
N2 C38 1.427(10) . ?
N3 C35 1.362(11) . ?
N3 C36 1.321(11) . ?
N4 C40 1.319(12) . ?
N4 C41 1.340(12) . ?
C33 C34 1.390(11) . ?
C33 C37 1.400(11) . ?
C34 H34 0.9500 . ?
C34 C35 1.371(11) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.366(11) . ?
C37 H37 0.9500 . ?
C38 C39 1.401(10) . ?
C38 C42 1.380(11) . ?
C39 H39 0.9500 . ?
C39 C40 1.375(11) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C41 C42 1.377(12) . ?
C42 H42 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C13 120.6(5) . . ?
C10 O2 C24 118.0(5) . . ?
C2 C1 I1 119.5(5) . . ?
C6 C1 I1 122.2(5) . . ?
C6 C1 C2 118.3(6) . . ?
F1 C2 C1 120.2(6) . . ?
F1 C2 C3 118.7(6) . . ?
C3 C2 C1 121.0(6) . . ?
F2 C3 C2 119.5(6) . . ?
F2 C3 C4 119.2(6) . . ?
C2 C3 C4 121.3(6) . . ?
O1 C4 C3 119.3(6) . . ?
O1 C4 C5 122.7(6) . . ?
C3 C4 C5 117.9(6) . . ?
F4 C5 C4 119.1(6) . . ?
F4 C5 C6 121.2(6) . . ?
C6 C5 C4 119.7(6) . . ?
F3 C6 C1 121.8(6) . . ?
F3 C6 C5 116.6(6) . . ?
C1 C6 C5 121.7(6) . . ?
C8 C7 I2 121.4(6) . . ?
C8 C7 C12 117.7(7) . . ?
C12 C7 I2 120.9(6) . . ?
F7 C8 C9 116.9(8) . . ?
C7 C8 F7 120.8(7) . . ?
C7 C8 C9 122.3(7) . . ?
F8 C9 C8 120.5(7) . . ?
F8 C9 C10 119.2(7) . . ?
C10 C9 C8 120.3(7) . . ?
O2 C10 C9 119.1(7) . . ?
O2 C10 C11 122.6(7) . . ?
C9 C10 C11 118.1(7) . . ?
F6 C11 C10 119.2(7) . . ?
F6 C11 C12 120.5(7) . . ?
C12 C11 C10 120.3(7) . . ?
F5 C12 C7 120.8(7) . . ?
F5 C12 C11 118.0(7) . . ?
C11 C12 C7 121.2(7) . . ?
O1 C13 C14 112.0(6) . . ?
C22 C13 O1 125.0(6) . . ?
C22 C13 C14 122.9(6) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(7) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.7(7) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 121.8(7) . . ?
C15 C16 C21 119.5(6) . . ?
C17 C16 C21 118.7(7) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(7) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(7) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(7) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C21 122.1(7) . . ?
C21 C20 H20 118.9 . . ?
C20 C21 C16 117.8(6) . . ?
C20 C21 C22 122.7(6) . . ?
C22 C21 C16 119.4(6) . . ?
C13 C22 C21 117.6(6) . . ?
C13 C22 C23 123.0(6) . . ?
C21 C22 C23 119.4(6) . . ?
C24 C23 C22 123.6(6) . . ?
C24 C23 C32 117.6(6) . . ?
C32 C23 C22 118.8(5) . . ?
O2 C24 C25 114.4(6) . . ?
C23 C24 O2 123.0(6) . . ?
C23 C24 C25 122.3(6) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.5(6) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(6) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 122.5(7) . . ?
C26 C27 C32 119.2(7) . . ?
C28 C27 C32 118.3(7) . . ?
C27 C28 H28 118.9 . . ?
C29 C28 C27 122.2(7) . . ?
C29 C28 H28 118.9 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.2(8) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.9(7) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.5 . . ?
C30 C31 C32 121.1(7) . . ?
C32 C31 H31 119.5 . . ?
C27 C32 C23 120.2(6) . . ?
C31 C32 C23 121.5(6) . . ?
C31 C32 C27 118.2(6) . . ?
N2 N1 C33 114.4(6) . . ?
N1 N2 C38 113.2(6) . . ?
C36 N3 C35 116.3(7) . . ?
C40 N4 C41 117.2(8) . . ?
C34 C33 N1 124.3(7) . . ?
C34 C33 C37 120.3(7) . . ?
C37 C33 N1 115.4(7) . . ?
C33 C34 H34 121.7 . . ?
C35 C34 C33 116.7(8) . . ?
C35 C34 H34 121.7 . . ?
N3 C35 C34 124.5(8) . . ?
N3 C35 H35 117.8 . . ?
C34 C35 H35 117.8 . . ?
N3 C36 H36 117.5 . . ?
N3 C36 C37 125.1(8) . . ?
C37 C36 H36 117.5 . . ?
C33 C37 H37 121.4 . . ?
C36 C37 C33 117.1(8) . . ?
C36 C37 H37 121.4 . . ?
C39 C38 N2 123.3(7) . . ?
C42 C38 N2 117.5(7) . . ?
C42 C38 C39 119.2(8) . . ?
C38 C39 H39 121.2 . . ?
C40 C39 C38 117.7(8) . . ?
C40 C39 H39 121.2 . . ?
N4 C40 C39 124.2(8) . . ?
N4 C40 H40 117.9 . . ?
C39 C40 H40 117.9 . . ?
N4 C41 H41 118.0 . . ?
N4 C41 C42 123.9(9) . . ?
C42 C41 H41 118.0 . . ?
C38 C42 H42 121.1 . . ?
C41 C42 C38 117.8(8) . . ?
C41 C42 H42 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 F1 -0.4(9) . . . . ?
I1 C1 C2 C3 179.3(5) . . . . ?
I1 C1 C6 F3 1.8(9) . . . . ?
I1 C1 C6 C5 -178.5(5) . . . . ?
I2 C7 C8 F7 4.0(10) . . . . ?
I2 C7 C8 C9 -177.3(5) . . . . ?
I2 C7 C12 F5 -2.1(10) . . . . ?
I2 C7 C12 C11 178.3(5) . . . . ?
F1 C2 C3 F2 -0.6(10) . . . . ?
F1 C2 C3 C4 177.7(6) . . . . ?
F2 C3 C4 O1 -1.6(10) . . . . ?
F2 C3 C4 C5 -178.0(6) . . . . ?
F4 C5 C6 F3 -0.4(10) . . . . ?
F4 C5 C6 C1 179.7(6) . . . . ?
F6 C11 C12 F5 0.1(11) . . . . ?
F6 C11 C12 C7 179.7(7) . . . . ?
F7 C8 C9 F8 -1.9(10) . . . . ?
F7 C8 C9 C10 177.7(6) . . . . ?
F8 C9 C10 O2 -3.0(10) . . . . ?
F8 C9 C10 C11 -178.5(6) . . . . ?
O1 C4 C5 F4 1.4(10) . . . . ?
O1 C4 C5 C6 -179.1(6) . . . . ?
O1 C13 C14 C15 175.6(6) . . . . ?
O1 C13 C22 C21 -178.6(6) . . . . ?
O1 C13 C22 C23 0.2(10) . . . . ?
O2 C10 C11 F6 3.1(11) . . . . ?
O2 C10 C11 C12 -176.4(7) . . . . ?
O2 C24 C25 C26 174.3(6) . . . . ?
C1 C2 C3 F2 179.7(6) . . . . ?
C1 C2 C3 C4 -2.0(11) . . . . ?
C2 C1 C6 F3 -178.2(7) . . . . ?
C2 C1 C6 C5 1.6(10) . . . . ?
C2 C3 C4 O1 -179.8(6) . . . . ?
C2 C3 C4 C5 3.7(10) . . . . ?
C3 C4 C5 F4 177.6(7) . . . . ?
C3 C4 C5 C6 -2.8(10) . . . . ?
C4 O1 C13 C14 147.5(6) . . . . ?
C4 O1 C13 C22 -36.4(9) . . . . ?
C4 C5 C6 F3 -180.0(6) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C6 C1 C2 F1 179.6(6) . . . . ?
C6 C1 C2 C3 -0.7(10) . . . . ?
C7 C8 C9 F8 179.4(7) . . . . ?
C7 C8 C9 C10 -1.1(11) . . . . ?
C8 C7 C12 F5 -178.6(6) . . . . ?
C8 C7 C12 C11 1.7(11) . . . . ?
C8 C9 C10 O2 177.5(6) . . . . ?
C8 C9 C10 C11 2.0(11) . . . . ?
C9 C10 C11 F6 178.4(6) . . . . ?
C9 C10 C11 C12 -1.1(11) . . . . ?
C10 O2 C24 C23 -49.1(9) . . . . ?
C10 O2 C24 C25 136.3(7) . . . . ?
C10 C11 C12 F5 179.6(7) . . . . ?
C10 C11 C12 C7 -0.8(11) . . . . ?
C12 C7 C8 F7 -179.5(6) . . . . ?
C12 C7 C8 C9 -0.8(11) . . . . ?
C13 O1 C4 C3 115.7(7) . . . . ?
C13 O1 C4 C5 -68.1(9) . . . . ?
C13 C14 C15 C16 2.5(11) . . . . ?
C13 C22 C23 C24 -79.9(9) . . . . ?
C13 C22 C23 C32 97.1(8) . . . . ?
C14 C13 C22 C21 -2.9(9) . . . . ?
C14 C13 C22 C23 175.8(6) . . . . ?
C14 C15 C16 C17 179.8(7) . . . . ?
C14 C15 C16 C21 -0.9(10) . . . . ?
C15 C16 C17 C18 -178.0(7) . . . . ?
C15 C16 C21 C20 177.9(6) . . . . ?
C15 C16 C21 C22 -2.6(10) . . . . ?
C16 C17 C18 C19 -0.7(12) . . . . ?
C16 C21 C22 C13 4.4(9) . . . . ?
C16 C21 C22 C23 -174.4(6) . . . . ?
C17 C16 C21 C20 -2.8(10) . . . . ?
C17 C16 C21 C22 176.8(6) . . . . ?
C17 C18 C19 C20 -1.1(12) . . . . ?
C18 C19 C20 C21 0.9(11) . . . . ?
C19 C20 C21 C16 1.1(10) . . . . ?
C19 C20 C21 C22 -178.5(7) . . . . ?
C20 C21 C22 C13 -176.1(6) . . . . ?
C20 C21 C22 C23 5.1(10) . . . . ?
C21 C16 C17 C18 2.7(11) . . . . ?
C21 C22 C23 C24 98.8(8) . . . . ?
C21 C22 C23 C32 -84.2(8) . . . . ?
C22 C13 C14 C15 -0.5(10) . . . . ?
C22 C23 C24 O2 1.2(10) . . . . ?
C22 C23 C24 C25 175.3(6) . . . . ?
C22 C23 C32 C27 -174.0(6) . . . . ?
C22 C23 C32 C31 2.9(9) . . . . ?
C23 C24 C25 C26 -0.4(11) . . . . ?
C24 O2 C10 C9 124.2(7) . . . . ?
C24 O2 C10 C11 -60.4(9) . . . . ?
C24 C23 C32 C27 3.2(9) . . . . ?
C24 C23 C32 C31 -179.9(6) . . . . ?
C24 C25 C26 C27 1.0(11) . . . . ?
C25 C26 C27 C28 -176.2(7) . . . . ?
C25 C26 C27 C32 0.6(10) . . . . ?
C26 C27 C28 C29 177.4(8) . . . . ?
C26 C27 C32 C23 -2.6(10) . . . . ?
C26 C27 C32 C31 -179.6(6) . . . . ?
C27 C28 C29 C30 1.7(12) . . . . ?
C28 C27 C32 C23 174.2(6) . . . . ?
C28 C27 C32 C31 -2.7(10) . . . . ?
C28 C29 C30 C31 -1.9(12) . . . . ?
C29 C30 C31 C32 -0.3(11) . . . . ?
C30 C31 C32 C23 -174.3(7) . . . . ?
C30 C31 C32 C27 2.6(10) . . . . ?
C32 C23 C24 O2 -175.9(6) . . . . ?
C32 C23 C24 C25 -1.7(10) . . . . ?
C32 C27 C28 C29 0.6(11) . . . . ?
N1 N2 C38 C39 13.1(10) . . . . ?
N1 N2 C38 C42 -169.0(6) . . . . ?
N1 C33 C34 C35 -179.3(7) . . . . ?
N1 C33 C37 C36 177.8(7) . . . . ?
N2 N1 C33 C34 14.0(10) . . . . ?
N2 N1 C33 C37 -163.6(7) . . . . ?
N2 C38 C39 C40 177.3(7) . . . . ?
N2 C38 C42 C41 -179.2(6) . . . . ?
N3 C36 C37 C33 1.9(14) . . . . ?
N4 C41 C42 C38 2.0(12) . . . . ?
C33 N1 N2 C38 -177.6(6) . . . . ?
C33 C34 C35 N3 2.0(13) . . . . ?
C34 C33 C37 C36 0.1(12) . . . . ?
C35 N3 C36 C37 -1.8(13) . . . . ?
C36 N3 C35 C34 -0.2(13) . . . . ?
C37 C33 C34 C35 -1.8(12) . . . . ?
C38 C39 C40 N4 1.9(12) . . . . ?
C39 C38 C42 C41 -1.1(11) . . . . ?
C40 N4 C41 C42 -0.8(12) . . . . ?
C41 N4 C40 C39 -1.2(12) . . . . ?
C42 C38 C39 C40 -0.6(11) . . . . ?


#End of file
####################################################################### 
# 
# 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_apy_2
_database_code_depnum_ccdc_archive 'CCDC 1868142'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2018-09-17 deposited with the CCDC.	2019-03-12 downloaded from the CCDC.
;
_audit_creation_date             2018-08-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 F8 I2 O2, C10 H8 N4'
_chemical_formula_sum            'C30 H22 F8 I2 N4 O2'
_chemical_formula_weight         876.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.2031(2)
_cell_length_b                   17.8566(4)
_cell_length_c                   32.8945(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3056.22(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    34384
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.143
_exptl_absorpt_correction_T_max  0.9017
_exptl_absorpt_correction_T_min  0.5781
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 3 0.0280
0 1 -1 0.0490
0 -1 1 0.0340
0 -1 -3 0.0280
-4 -1 1 0.2110
4 1 -1 0.2540
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            38579
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.254
_diffrn_reflns_theta_min         2.180
_diffrn_ambient_temperature      119.99
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                6979
_reflns_number_total             8255
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction        'STOE X-Area'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.316
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 
;
 Flack x determined using 2672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         8255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+1.1536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I1 I 0.74442(7) 0.35257(2) 0.59112(2) 0.02985(9) Uani 1 1 d . . . . .
I2 I 0.44621(7) 0.35961(2) 0.90528(2) 0.03136(10) Uani 1 1 d . . . . .
F1 F 1.1225(6) 0.41981(19) 0.65979(10) 0.0313(7) Uani 1 1 d . . . . .
F2 F 1.1110(6) 0.54715(19) 0.70231(11) 0.0348(8) Uani 1 1 d . . . . .
F3 F 0.3876(7) 0.62687(18) 0.62724(10) 0.0336(8) Uani 1 1 d . . . . .
F4 F 0.3875(6) 0.49796(19) 0.58678(10) 0.0355(8) Uani 1 1 d . . . . .
F5 F 0.0874(6) 0.50364(18) 0.90871(11) 0.0354(7) Uani 1 1 d . . . . .
F6 F 0.0922(6) 0.63458(19) 0.87007(10) 0.0341(7) Uani 1 1 d . . . . .
F7 F 0.8238(7) 0.55785(19) 0.79634(11) 0.0352(8) Uani 1 1 d . . . . .
F8 F 0.8247(7) 0.42726(19) 0.83636(10) 0.0333(8) Uani 1 1 d . . . . .
O1 O 0.7635(8) 0.6566(2) 0.68679(12) 0.0316(8) Uani 1 1 d . . . . .
O2 O 0.4839(7) 0.6671(2) 0.81345(12) 0.0292(9) Uani 1 1 d . . . . .
C1 C 0.7531(11) 0.4549(3) 0.62222(15) 0.0246(10) Uani 1 1 d . . . . .
C2 C 0.9368(11) 0.4706(3) 0.65149(16) 0.0260(11) Uani 1 1 d . . . . .
C3 C 0.9331(11) 0.5359(3) 0.67323(16) 0.0258(11) Uani 1 1 d . . . . .
C4 C 0.7493(12) 0.5907(3) 0.66653(16) 0.0266(11) Uani 1 1 d . . . . .
C5 C 0.5661(11) 0.5759(3) 0.63631(16) 0.0253(11) Uani 1 1 d . . . . .
C6 C 0.5700(11) 0.5088(3) 0.61533(15) 0.0254(11) Uani 1 1 d . . . . .
C7 C 0.5395(11) 0.6720(3) 0.71164(17) 0.0288(11) Uani 1 1 d . . . . .
H7A H 0.501264 0.628360 0.729164 0.035 Uiso 1 1 calc R . . . .
H7B H 0.388489 0.681364 0.694035 0.035 Uiso 1 1 calc R . . . .
C8 C 0.5924(10) 0.7406(3) 0.73787(16) 0.0231(10) Uani 1 1 d . . . . .
H8 H 0.739815 0.729203 0.756376 0.028 Uiso 1 1 calc R . . . .
C9 C 0.6622(11) 0.8083(3) 0.71187(17) 0.0264(11) Uani 1 1 d . . . . .
H9A H 0.819614 0.796908 0.696119 0.032 Uiso 1 1 calc R . . . .
H9B H 0.521641 0.818004 0.692290 0.032 Uiso 1 1 calc R . . . .
C10 C 0.7075(11) 0.8782(3) 0.73724(18) 0.0267(11) Uani 1 1 d . . . . .
H10A H 0.743446 0.921139 0.719081 0.032 Uiso 1 1 calc R . . . .
H10B H 0.859125 0.870599 0.754949 0.032 Uiso 1 1 calc R . . . .
C11 C 0.4722(11) 0.8955(3) 0.76343(18) 0.0279(11) Uani 1 1 d . . . . .
H11A H 0.509611 0.938917 0.781206 0.034 Uiso 1 1 calc R . . . .
H11B H 0.325561 0.908937 0.745689 0.034 Uiso 1 1 calc R . . . .
C12 C 0.4013(11) 0.8287(3) 0.78926(16) 0.0249(11) Uani 1 1 d . . . . .
H12A H 0.243827 0.840364 0.804907 0.030 Uiso 1 1 calc R . . . .
H12B H 0.541329 0.818836 0.808922 0.030 Uiso 1 1 calc R . . . .
C13 C 0.3550(10) 0.7583(3) 0.76383(16) 0.0218(10) Uani 1 1 d . . . . .
H13 H 0.211779 0.770034 0.744598 0.026 Uiso 1 1 calc R . . . .
C14 C 0.2663(11) 0.6931(3) 0.78982(16) 0.0257(10) Uani 1 1 d . . . . .
H14A H 0.125939 0.709307 0.808131 0.031 Uiso 1 1 calc R . . . .
H14B H 0.200941 0.652201 0.772324 0.031 Uiso 1 1 calc R . . . .
C15 C 0.4590(12) 0.5999(3) 0.83187(16) 0.0259(11) Uani 1 1 d . . . . .
C16 C 0.2737(12) 0.5831(3) 0.86067(16) 0.0272(11) Uani 1 1 d . . . . .
C17 C 0.2719(11) 0.5151(3) 0.88088(16) 0.0275(11) Uani 1 1 d . . . . .
C18 C 0.4552(12) 0.4612(3) 0.87389(16) 0.0277(11) Uani 1 1 d . . . . .
C19 C 0.6410(11) 0.4774(3) 0.84480(17) 0.0268(11) Uani 1 1 d . . . . .
C20 C 0.6423(11) 0.5448(3) 0.82453(16) 0.0262(11) Uani 1 1 d . . . . .
N1 N 0.4995(12) 0.0074(3) 0.49588(18) 0.0462(14) Uani 1 1 d . . . . .
N2 N 0.2918(13) -0.0169(4) 0.50279(18) 0.0480(15) Uani 1 1 d . . . . .
N3 N 0.6654(11) 0.2147(3) 0.55168(16) 0.0338(11) Uani 1 1 d . . . . .
N4 N 0.1284(11) -0.2221(3) 0.44536(16) 0.0352(12) Uani 1 1 d . . . . .
C21 C 0.8066(13) 0.1846(4) 0.5225(2) 0.0373(14) Uani 1 1 d . . . . .
H21 H 0.955282 0.210650 0.513489 0.045 Uiso 1 1 calc R . . . .
C22 C 0.7471(16) 0.1172(4) 0.50470(19) 0.0408(14) Uani 1 1 d . . . . .
H22 H 0.852106 0.097588 0.483614 0.049 Uiso 1 1 calc R . . . .
C23 C 0.5378(16) 0.0791(3) 0.5174(2) 0.0389(15) Uani 1 1 d . . . . .
C24 C 0.3874(14) 0.1088(4) 0.5481(2) 0.0451(17) Uani 1 1 d . . . . .
H24 H 0.238857 0.083215 0.557518 0.054 Uiso 1 1 calc R . . . .
C25 C 0.4595(13) 0.1772(4) 0.56484(19) 0.0353(13) Uani 1 1 d . . . . .
H25 H 0.359406 0.197876 0.586224 0.042 Uiso 1 1 calc R . . . .
C26 C -0.0102(13) -0.1931(4) 0.4749(2) 0.0401(15) Uani 1 1 d . . . . .
H26 H -0.157038 -0.220120 0.483840 0.048 Uiso 1 1 calc R . . . .
C27 C 0.0449(16) -0.1264(4) 0.4935(2) 0.0427(15) Uani 1 1 d . . . . .
H27 H -0.061775 -0.107491 0.514585 0.051 Uiso 1 1 calc R . . . .
C28 C 0.2568(16) -0.0879(3) 0.48098(19) 0.0388(15) Uani 1 1 d . . . . .
C29 C 0.4051(13) -0.1168(4) 0.4504(2) 0.0385(15) Uani 1 1 d . . . . .
H29 H 0.553975 -0.090929 0.441289 0.046 Uiso 1 1 calc R . . . .
C30 C 0.3347(14) -0.1839(4) 0.43312(19) 0.0378(14) Uani 1 1 d . . . . .
H30 H 0.436652 -0.203728 0.411718 0.045 Uiso 1 1 calc R . . . .


_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
I1 C1 2.094(5) . ?
I2 C18 2.088(5) . ?
F1 C2 1.352(6) . ?
F2 C3 1.346(6) . ?
F3 C5 1.335(6) . ?
F4 C6 1.349(6) . ?
F5 C17 1.342(6) . ?
F6 C16 1.354(6) . ?
F7 C20 1.344(6) . ?
F8 C19 1.339(7) . ?
O1 C4 1.354(6) . ?
O1 C7 1.450(7) . ?
O2 C14 1.450(6) . ?
O2 C15 1.350(6) . ?
C1 C2 1.385(8) . ?
C1 C6 1.373(8) . ?
C2 C3 1.368(7) . ?
C3 C4 1.387(8) . ?
C4 C5 1.403(8) . ?
C5 C6 1.382(7) . ?
C7 C8 1.523(7) . ?
C8 C9 1.525(7) . ?
C8 C13 1.535(7) . ?
C9 C10 1.520(7) . ?
C10 C11 1.529(8) . ?
C11 C12 1.511(8) . ?
C12 C13 1.529(7) . ?
C13 C14 1.516(7) . ?
C15 C16 1.385(8) . ?
C15 C20 1.392(8) . ?
C16 C17 1.384(8) . ?
C17 C18 1.374(8) . ?
C18 C19 1.390(8) . ?
C19 C20 1.375(8) . ?
N1 N2 1.187(8) . ?
N1 C23 1.477(9) . ?
N2 C28 1.468(9) . ?
N3 C21 1.323(8) . ?
N3 C25 1.335(9) . ?
N4 C26 1.316(9) . ?
N4 C30 1.334(9) . ?
C21 C22 1.373(9) . ?
C22 C23 1.351(11) . ?
C23 C24 1.383(10) . ?
C24 C25 1.391(9) . ?
C26 C27 1.370(10) . ?
C27 C28 1.364(12) . ?
C28 C29 1.368(10) . ?
C29 C30 1.377(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
C4 O1 C7 113.5(4) . . ?
C15 O2 C14 116.8(4) . . ?
C2 C1 I1 122.0(4) . . ?
C6 C1 I1 121.1(4) . . ?
C6 C1 C2 116.9(5) . . ?
F1 C2 C1 119.9(5) . . ?
F1 C2 C3 118.4(5) . . ?
C3 C2 C1 121.7(5) . . ?
F2 C3 C2 119.3(5) . . ?
F2 C3 C4 118.8(5) . . ?
C2 C3 C4 121.9(5) . . ?
O1 C4 C3 119.9(5) . . ?
O1 C4 C5 123.4(5) . . ?
C3 C4 C5 116.6(5) . . ?
F3 C5 C4 120.1(5) . . ?
F3 C5 C6 119.3(5) . . ?
C6 C5 C4 120.5(5) . . ?
F4 C6 C1 120.2(5) . . ?
F4 C6 C5 117.5(5) . . ?
C1 C6 C5 122.3(5) . . ?
O1 C7 C8 109.1(4) . . ?
C7 C8 C9 111.3(4) . . ?
C7 C8 C13 109.6(4) . . ?
C9 C8 C13 109.9(4) . . ?
C10 C9 C8 112.3(4) . . ?
C9 C10 C11 110.6(5) . . ?
C12 C11 C10 110.6(4) . . ?
C11 C12 C13 112.4(4) . . ?
C12 C13 C8 110.3(4) . . ?
C14 C13 C8 113.6(4) . . ?
C14 C13 C12 111.8(4) . . ?
O2 C14 C13 108.1(4) . . ?
O2 C15 C16 124.5(5) . . ?
O2 C15 C20 119.0(5) . . ?
C16 C15 C20 116.2(5) . . ?
F6 C16 C15 119.6(5) . . ?
F6 C16 C17 118.8(5) . . ?
C17 C16 C15 121.6(5) . . ?
F5 C17 C16 117.8(5) . . ?
F5 C17 C18 120.3(5) . . ?
C18 C17 C16 121.9(5) . . ?
C17 C18 I2 120.7(4) . . ?
C17 C18 C19 116.9(5) . . ?
C19 C18 I2 122.4(4) . . ?
F8 C19 C18 120.0(5) . . ?
F8 C19 C20 118.7(5) . . ?
C20 C19 C18 121.3(5) . . ?
F7 C20 C15 118.6(5) . . ?
F7 C20 C19 119.3(5) . . ?
C19 C20 C15 122.1(5) . . ?
N2 N1 C23 110.4(7) . . ?
N1 N2 C28 109.6(7) . . ?
C21 N3 C25 118.5(6) . . ?
C26 N4 C30 117.6(6) . . ?
N3 C21 C22 122.7(7) . . ?
C23 C22 C21 119.4(7) . . ?
C22 C23 N1 113.3(7) . . ?
C22 C23 C24 119.3(6) . . ?
C24 C23 N1 127.3(7) . . ?
C23 C24 C25 118.2(7) . . ?
N3 C25 C24 121.9(6) . . ?
N4 C26 C27 123.8(7) . . ?
C28 C27 C26 118.2(7) . . ?
C27 C28 N2 112.8(6) . . ?
C27 C28 C29 119.2(6) . . ?
C29 C28 N2 127.9(7) . . ?
C28 C29 C30 118.8(6) . . ?
N4 C30 C29 122.3(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 F1 2.0(7) . . . . ?
I1 C1 C2 C3 -176.4(4) . . . . ?
I1 C1 C6 F4 -3.2(7) . . . . ?
I1 C1 C6 C5 177.9(4) . . . . ?
I2 C18 C19 F8 -0.8(7) . . . . ?
I2 C18 C19 C20 179.9(4) . . . . ?
F1 C2 C3 F2 -0.8(8) . . . . ?
F1 C2 C3 C4 179.9(5) . . . . ?
F2 C3 C4 O1 5.3(8) . . . . ?
F2 C3 C4 C5 -179.1(5) . . . . ?
F3 C5 C6 F4 -1.0(8) . . . . ?
F3 C5 C6 C1 177.9(5) . . . . ?
F5 C17 C18 I2 1.4(7) . . . . ?
F5 C17 C18 C19 -179.6(5) . . . . ?
F6 C16 C17 F5 0.6(8) . . . . ?
F6 C16 C17 C18 -177.8(5) . . . . ?
F8 C19 C20 F7 1.3(8) . . . . ?
F8 C19 C20 C15 -179.5(5) . . . . ?
O1 C4 C5 F3 -2.6(9) . . . . ?
O1 C4 C5 C6 176.7(5) . . . . ?
O1 C7 C8 C9 57.3(6) . . . . ?
O1 C7 C8 C13 179.1(4) . . . . ?
O2 C15 C16 F6 4.1(9) . . . . ?
O2 C15 C16 C17 -174.5(5) . . . . ?
O2 C15 C20 F7 -6.3(8) . . . . ?
O2 C15 C20 C19 174.5(5) . . . . ?
C1 C2 C3 F2 177.7(5) . . . . ?
C1 C2 C3 C4 -1.6(9) . . . . ?
C2 C1 C6 F4 178.9(5) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
C2 C3 C4 O1 -175.4(5) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 F3 -178.0(5) . . . . ?
C3 C4 C5 C6 1.3(8) . . . . ?
C4 O1 C7 C8 171.3(5) . . . . ?
C4 C5 C6 F4 179.7(5) . . . . ?
C4 C5 C6 C1 -1.4(9) . . . . ?
C6 C1 C2 F1 179.9(5) . . . . ?
C6 C1 C2 C3 1.5(8) . . . . ?
C7 O1 C4 C3 -120.2(6) . . . . ?
C7 O1 C4 C5 64.5(7) . . . . ?
C7 C8 C9 C10 178.1(5) . . . . ?
C7 C8 C13 C12 -178.0(4) . . . . ?
C7 C8 C13 C14 55.6(6) . . . . ?
C8 C9 C10 C11 -56.3(6) . . . . ?
C8 C13 C14 O2 53.3(6) . . . . ?
C9 C8 C13 C12 -55.4(6) . . . . ?
C9 C8 C13 C14 178.2(4) . . . . ?
C9 C10 C11 C12 55.0(7) . . . . ?
C10 C11 C12 C13 -56.1(6) . . . . ?
C11 C12 C13 C8 56.5(6) . . . . ?
C11 C12 C13 C14 -176.1(5) . . . . ?
C12 C13 C14 O2 -72.3(6) . . . . ?
C13 C8 C9 C10 56.5(6) . . . . ?
C14 O2 C15 C16 -60.5(7) . . . . ?
C14 O2 C15 C20 125.2(6) . . . . ?
C15 O2 C14 C13 -166.3(4) . . . . ?
C15 C16 C17 F5 179.2(5) . . . . ?
C15 C16 C17 C18 0.9(9) . . . . ?
C16 C15 C20 F7 178.9(5) . . . . ?
C16 C15 C20 C19 -0.3(8) . . . . ?
C16 C17 C18 I2 179.7(4) . . . . ?
C16 C17 C18 C19 -1.3(8) . . . . ?
C17 C18 C19 F8 -179.7(5) . . . . ?
C17 C18 C19 C20 0.9(8) . . . . ?
C18 C19 C20 F7 -179.3(5) . . . . ?
C18 C19 C20 C15 -0.1(9) . . . . ?
C20 C15 C16 F6 178.6(5) . . . . ?
C20 C15 C16 C17 0.0(8) . . . . ?
N1 N2 C28 C27 167.9(6) . . . . ?
N1 N2 C28 C29 -13.5(10) . . . . ?
N1 C23 C24 C25 179.1(6) . . . . ?
N2 N1 C23 C22 -167.4(7) . . . . ?
N2 N1 C23 C24 13.1(10) . . . . ?
N2 C28 C29 C30 -178.3(6) . . . . ?
N3 C21 C22 C23 -0.6(10) . . . . ?
N4 C26 C27 C28 -0.6(10) . . . . ?
C21 N3 C25 C24 -1.5(9) . . . . ?
C21 C22 C23 N1 -179.4(6) . . . . ?
C21 C22 C23 C24 0.1(10) . . . . ?
C22 C23 C24 C25 -0.3(10) . . . . ?
C23 N1 N2 C28 179.7(5) . . . . ?
C23 C24 C25 N3 1.0(9) . . . . ?
C25 N3 C21 C22 1.3(10) . . . . ?
C26 N4 C30 C29 0.4(9) . . . . ?
C26 C27 C28 N2 179.0(6) . . . . ?
C26 C27 C28 C29 0.3(10) . . . . ?
C27 C28 C29 C30 0.2(10) . . . . ?
C28 C29 C30 N4 -0.6(10) . . . . ?
C30 N4 C26 C27 0.2(10) . . . . ?

