#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:53:17 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235216 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/36/1553621.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1553621
loop_
_publ_author_name
'Almeida, José'
'Aguiar, António'
'Leite, Andreia'
'Silva, André M. N.'
'Cunha-Silva, Luís'
'de Castro, Baltazar'
'Rangel, Maria'
'Barone, Giampaolo'
'Tomé, Augusto C.'
'Silva, Ana M. G.'
_publ_section_title
;
 1,3-Dipolar cycloadditions with meso-tetraarylchlorins -- site
 selectivity and mixed bisadducts
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              534
_journal_paper_doi               10.1039/C6QO00771F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C60 H28 F20 N6 O2'
_chemical_formula_sum            'C60 H28 F20 N6 O2'
_chemical_formula_weight         1244.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             '28 June 2016'
_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_audit_update_record
;
2016-11-29 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                102.651(5)
_cell_angle_beta                 95.439(6)
_cell_angle_gamma                92.290(6)
_cell_formula_units_Z            2
_cell_length_a                   12.4994(13)
_cell_length_b                   13.1859(14)
_cell_length_c                   16.0253(17)
_cell_measurement_reflns_used    7343
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      21.44
_cell_measurement_theta_min      2.21
_cell_volume                     2560.5(5)
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            51921
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.660
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       prism
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.396
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.050(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.614
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     681
_refine_ls_number_reflns         8926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.614
_refine_ls_R_factor_all          0.1877
_refine_ls_R_factor_gt           0.1387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4059
_refine_ls_wR_factor_ref         0.4340
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5527
_reflns_number_total             8926
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6qo00771f2.cif
_cod_data_source_block           as0214
_cod_database_code               1553621
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
F1 F 0.5039(4) 0.7241(3) 0.2509(3) 0.0687(12) Uani 1 1 d . .
F2 F 0.4424(4) 0.8705(4) 0.1655(3) 0.0865(15) Uani 1 1 d . .
F3 F 0.2802(4) 0.9919(3) 0.2175(3) 0.0721(13) Uani 1 1 d . .
F4 F 0.1866(4) 0.9722(3) 0.3601(3) 0.0698(12) Uani 1 1 d . .
F5 F 0.2531(3) 0.8316(3) 0.4480(2) 0.0556(11) Uani 1 1 d . .
F6 F 0.0757(3) 0.4215(3) 0.5199(3) 0.0714(13) Uani 1 1 d . .
F7 F -0.1194(3) 0.3207(4) 0.4815(3) 0.0840(15) Uani 1 1 d . .
F8 F -0.1509(3) 0.1463(4) 0.3540(3) 0.0759(13) Uani 1 1 d . .
F9 F 0.0122(4) 0.0765(3) 0.2620(3) 0.0762(13) Uani 1 1 d . .
F10 F 0.2063(3) 0.1816(3) 0.2960(3) 0.0662(12) Uani 1 1 d . .
O1 O 0.2319(10) 0.5758(8) 0.2385(9) 0.175(4) Uani 1 1 d . .
N1 N 0.5682(4) 0.6432(4) 0.4891(3) 0.0424(13) Uani 1 1 d . .
H1 H 0.5401 0.5831 0.4947 0.051 Uiso 1 1 calc R U
N2 N 0.3598(4) 0.5221(4) 0.4294(3) 0.0429(13) Uani 1 1 d . .
N3 N 0.2200(9) 0.4613(9) 0.2179(7) 0.126(3) Uani 1 1 d . .
C1 C 0.6680(5) 0.6848(5) 0.5234(4) 0.0404(15) Uani 1 1 d . .
C2 C 0.6818(5) 0.7825(5) 0.4998(4) 0.0488(16) Uani 1 1 d . .
H2 H 0.7439 0.8293 0.5144 0.059 Uiso 1 1 calc R U
C3 C 0.5892(5) 0.7958(5) 0.4525(4) 0.0443(15) Uani 1 1 d . .
H3 H 0.5755 0.8548 0.4290 0.053 Uiso 1 1 calc R U
C4 C 0.5170(5) 0.7091(5) 0.4440(4) 0.0413(15) Uani 1 1 d . .
C5 C 0.4149(5) 0.6913(4) 0.3996(4) 0.0376(14) Uani 1 1 d . .
C6 C 0.3420(5) 0.6046(4) 0.3909(4) 0.0411(15) Uani 1 1 d . .
C7 C 0.2343(5) 0.5922(5) 0.3399(4) 0.0488(16) Uani 1 1 d . .
H7 H 0.1910 0.6523 0.3626 0.059 Uiso 1 1 calc R U
C9 C 0.2696(5) 0.4586(4) 0.4074(4) 0.0406(15) Uani 1 1 d . .
C10 C 0.3803(3) 0.7740(3) 0.3519(2) 0.0410(15) Uani 1 1 d G .
C11 C 0.2986(3) 0.8376(3) 0.3794(2) 0.0473(16) Uani 1 1 d G .
C12 C 0.2649(3) 0.9113(3) 0.3341(3) 0.0512(17) Uani 1 1 d G .
C13 C 0.3129(4) 0.9213(3) 0.2613(3) 0.0553(18) Uani 1 1 d G .
C14 C 0.3945(4) 0.8576(3) 0.2338(2) 0.0586(19) Uani 1 1 d G .
C15 C 0.4282(3) 0.7839(3) 0.2791(3) 0.0511(17) Uani 1 1 d G .
C16 C 0.2552(5) 0.3628(4) 0.4316(4) 0.0399(15) Uani 1 1 d . .
C17 C 0.1470(5) 0.3056(5) 0.4077(4) 0.0400(14) Uani 1 1 d . .
C18 C 0.0615(5) 0.3388(5) 0.4553(5) 0.0533(18) Uani 1 1 d . .
C19 C -0.0394(5) 0.2877(6) 0.4370(5) 0.0576(18) Uani 1 1 d . .
C20 C -0.0553(6) 0.1981(5) 0.3706(5) 0.0569(18) Uani 1 1 d . .
C21 C 0.0273(6) 0.1635(5) 0.3239(5) 0.0523(18) Uani 1 1 d . .
C22 C 0.1267(5) 0.2177(5) 0.3431(4) 0.0479(16) Uani 1 1 d . .
C23 C 0.1865(6) 0.4997(5) 0.3548(4) 0.0506(17) Uani 1 1 d . .
H23 H 0.1247 0.5183 0.3895 0.061 Uiso 1 1 calc R U
C24 C 0.1428(7) 0.4326(7) 0.2679(5) 0.073(2) Uani 1 1 d . .
H24A H 0.1419 0.3575 0.2677 0.087 Uiso 1 1 calc R U
H24B H 0.0697 0.4508 0.2490 0.087 Uiso 1 1 calc R U
C25 C 0.1782(15) 0.4236(10) 0.1247(7) 0.148(6) Uani 1 1 d . .
H25A H 0.2288 0.4484 0.0885 0.178 Uiso 1 1 calc R U
H25B H 0.1078 0.4526 0.1136 0.178 Uiso 1 1 calc R U
C26 C 0.1652(11) 0.3041(8) 0.1004(8) 0.144(5) Uiso 1 1 d G .
C27 C 0.2411(9) 0.2520(11) 0.0520(9) 0.180(7) Uiso 1 1 d G .
H27 H 0.3027 0.2895 0.0409 0.216 Uiso 1 1 calc R U
C28 C 0.2269(11) 0.1450(11) 0.0198(9) 0.255(12) Uiso 1 1 d G .
H28 H 0.2788 0.1093 -0.0133 0.306 Uiso 1 1 calc R U
C29 C 0.1368(13) 0.0901(8) 0.0360(9) 0.159(6) Uiso 1 1 d G .
H29 H 0.1270 0.0170 0.0140 0.191 Uiso 1 1 calc R U
C30 C 0.0609(10) 0.1423(10) 0.0844(9) 0.276(13) Uiso 1 1 d G .
H30 H -0.0007 0.1048 0.0955 0.331 Uiso 1 1 calc R U
C31 C 0.0751(10) 0.2493(10) 0.1166(8) 0.160(6) Uiso 1 1 d G .
H31 H 0.0232 0.2849 0.1497 0.192 Uiso 1 1 calc R U
F11 F 0.1500(9) 0.8195(6) -0.1429(5) 0.151(3) Uani 1 1 d . .
F12 F 0.3032(13) 0.9541(7) -0.1696(6) 0.233(7) Uani 1 1 d . .
F13 F 0.5100(10) 0.9526(7) -0.0985(6) 0.221(6) Uani 1 1 d . .
F14 F 0.5615(7) 0.8197(7) 0.0096(6) 0.163(3) Uani 1 1 d . .
F15 F 0.4043(6) 0.6902(5) 0.0341(5) 0.125(2) Uani 1 1 d . .
F16 F 0.0431(4) 0.7538(4) 0.3291(3) 0.0824(15) Uani 1 1 d . .
F17 F -0.0195(5) 0.8915(4) 0.4606(3) 0.0894(16) Uani 1 1 d . .
F18 F -0.2124(4) 0.9807(3) 0.4417(3) 0.0772(14) Uani 1 1 d . .
F19 F -0.3383(4) 0.9268(4) 0.2905(3) 0.0794(14) Uani 1 1 d . .
F20 F -0.2751(4) 0.7878(4) 0.1584(3) 0.0755(13) Uani 1 1 d . .
O2 O -0.2263(9) 0.3917(8) 0.2262(7) 0.148(3) Uani 1 1 d . .
N4 N 0.0478(5) 0.6559(4) 0.0552(3) 0.0506(14) Uani 1 1 d . .
H4 H 0.0284 0.5899 0.0327 0.061 Uiso 1 1 calc R U
N5 N -0.1102(5) 0.5043(4) 0.0874(4) 0.0587(16) Uani 1 1 d . .
N6 N -0.2243(12) 0.4556(10) 0.3080(8) 0.155(5) Uani 1 1 d . .
C32 C 0.1258(6) 0.7117(5) 0.0283(4) 0.0517(17) Uani 1 1 d . .
C33 C 0.1319(6) 0.8139(5) 0.0822(4) 0.0527(18) Uani 1 1 d . .
H33 H 0.1801 0.8700 0.0788 0.063 Uiso 1 1 calc R U
C34 C 0.0591(6) 0.8178(5) 0.1383(4) 0.0501(17) Uani 1 1 d . .
H34 H 0.0465 0.8772 0.1810 0.060 Uiso 1 1 calc R U
C35 C 0.0027(5) 0.7175(5) 0.1235(4) 0.0463(16) Uani 1 1 d . .
C36 C -0.0776(6) 0.6858(5) 0.1666(4) 0.0509(17) Uani 1 1 d . .
C37 C -0.1319(6) 0.5884(6) 0.1516(5) 0.061(2) Uani 1 1 d . .
C38 C -0.2146(7) 0.5596(6) 0.2034(5) 0.071(2) Uani 1 1 d . .
H38 H -0.2774 0.6040 0.2015 0.085 Uiso 1 1 calc R U
C39 C -0.2463(9) 0.4518(7) 0.1641(6) 0.082(3) Uani 1 1 d . .
H39 H -0.3242 0.4439 0.1411 0.098 Uiso 1 1 calc R U
C40 C -0.1776(7) 0.4238(6) 0.0931(5) 0.065(2) Uani 1 1 d . .
C41 C 0.1868(6) 0.6742(5) -0.0390(4) 0.0569(19) Uani 1 1 d . .
C42 C 0.2743(5) 0.7509(4) -0.0550(4) 0.078(3) Uani 1 1 d G .
C43 C 0.2509(6) 0.8198(5) -0.1076(4) 0.124(5) Uani 1 1 d G .
C44 C 0.3318(8) 0.8875(5) -0.1218(5) 0.132(6) Uani 1 1 d G .
C45 C 0.4361(7) 0.8862(6) -0.0835(6) 0.116(4) Uiso 1 1 d G .
C46 C 0.4596(5) 0.8173(6) -0.0309(5) 0.130(5) Uani 1 1 d G .
C47 C 0.3787(6) 0.7496(5) -0.0167(4) 0.086(3) Uani 1 1 d G .
C48 C -0.1122(6) 0.7669(5) 0.2405(4) 0.0551(18) Uani 1 1 d . .
C49 C -0.0515(5) 0.7958(5) 0.3166(4) 0.0488(17) Uani 1 1 d . .
C50 C -0.0845(6) 0.8683(5) 0.3859(4) 0.0548(18) Uani 1 1 d . .
C51 C -0.1772(7) 0.9114(5) 0.3765(5) 0.058(2) Uani 1 1 d . .
C52 C -0.2446(6) 0.8842(6) 0.2993(5) 0.0566(19) Uani 1 1 d . .
C53 C -0.2098(5) 0.8124(5) 0.2328(4) 0.0494(17) Uani 1 1 d . .
C54 C -0.1768(15) 0.5551(12) 0.2963(11) 0.165(7) Uani 1 1 d . .
H54A H -0.0972 0.5572 0.3054 0.198 Uiso 1 1 calc R U
H54B H -0.2022 0.6145 0.3373 0.198 Uiso 1 1 calc R U
C55 C -0.3381(19) 0.459(2) 0.3306(13) 0.243(12) Uani 1 1 d . .
H55A H -0.3363 0.5011 0.3900 0.291 Uiso 1 1 calc R U
H55B H -0.3781 0.4974 0.2924 0.291 Uiso 1 1 calc R U
C56 C -0.3961(6) 0.3701(5) 0.3265(5) 0.088(3) Uiso 1 1 d G .
C57 C -0.3599(5) 0.2962(6) 0.3706(4) 0.089(3) Uiso 1 1 d G .
H57 H -0.2942 0.3097 0.4074 0.107 Uiso 1 1 calc R U
C58 C -0.4197(8) 0.2024(6) 0.3609(6) 0.128(4) Uiso 1 1 d G .
H58 H -0.3949 0.1519 0.3911 0.153 Uiso 1 1 calc R U
C59 C -0.5157(8) 0.1826(7) 0.3071(7) 0.180(7) Uiso 1 1 d G .
H59 H -0.5566 0.1185 0.3005 0.216 Uiso 1 1 calc R U
C60 C -0.5519(6) 0.2565(9) 0.2630(7) 0.168(6) Uiso 1 1 d G .
H60 H -0.6175 0.2430 0.2262 0.202 Uiso 1 1 calc R U
C61 C -0.4921(7) 0.3503(7) 0.2727(5) 0.131(4) Uiso 1 1 d G .
H61 H -0.5169 0.4008 0.2425 0.157 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N3 O1 C7 97.1(9) . .
C1 N1 C4 110.1(5) . .
C1 N1 H1 125.0 . .
C4 N1 H1 125.0 . .
C9 N2 C6 105.7(5) . .
C24 N3 O1 107.1(10) . .
C24 N3 C25 108.4(11) . .
O1 N3 C25 109.0(10) . .
N1 C1 C16 126.0(5) . 2_666
N1 C1 C2 107.2(5) . .
C16 C1 C2 126.7(6) 2_666 .
C3 C2 C1 107.1(6) . .
C3 C2 H2 126.5 . .
C1 C2 H2 126.5 . .
C2 C3 C4 109.4(5) . .
C2 C3 H3 125.3 . .
C4 C3 H3 125.3 . .
N1 C4 C5 126.2(6) . .
N1 C4 C3 106.2(5) . .
C5 C4 C3 127.6(6) . .
C4 C5 C6 128.0(5) . .
C4 C5 C10 115.4(5) . .
C6 C5 C10 116.6(5) . .
N2 C6 C5 124.6(5) . .
N2 C6 C7 111.6(5) . .
C5 C6 C7 123.7(5) . .
C23 C7 C6 104.2(6) . .
C23 C7 O1 106.3(6) . .
C6 C7 O1 117.3(7) . .
C23 C7 H7 109.6 . .
C6 C7 H7 109.6 . .
O1 C7 H7 109.6 . .
N2 C9 C16 124.3(6) . .
N2 C9 C23 112.7(5) . .
C16 C9 C23 123.0(5) . .
C11 C10 C15 120.0 . .
C11 C10 C5 120.2(3) . .
C15 C10 C5 119.8(3) . .
F5 C11 C12 118.3(3) . .
F5 C11 C10 121.7(3) . .
C12 C11 C10 120.0 . .
F4 C12 C11 120.2(3) . .
F4 C12 C13 119.8(3) . .
C11 C12 C13 120.0 . .
F3 C13 C14 120.0(4) . .
F3 C13 C12 120.0(4) . .
C14 C13 C12 120.0 . .
F2 C14 C15 120.6(4) . .
F2 C14 C13 119.4(4) . .
C15 C14 C13 120.0 . .
F1 C15 C14 118.6(3) . .
F1 C15 C10 121.4(3) . .
C14 C15 C10 120.0 . .
C1 C16 C9 126.6(6) 2_666 .
C1 C16 C17 115.9(5) 2_666 .
C9 C16 C17 117.5(5) . .
C22 C17 C18 116.7(6) . .
C22 C17 C16 123.5(5) . .
C18 C17 C16 119.7(5) . .
F6 C18 C19 117.8(6) . .
F6 C18 C17 120.2(6) . .
C19 C18 C17 122.1(6) . .
F7 C19 C18 121.4(7) . .
F7 C19 C20 120.0(6) . .
C18 C19 C20 118.7(6) . .
F8 C20 C21 120.3(6) . .
F8 C20 C19 119.4(6) . .
C21 C20 C19 120.3(6) . .
F9 C21 C20 120.0(6) . .
F9 C21 C22 120.7(7) . .
C20 C21 C22 119.3(6) . .
F10 C22 C17 119.3(6) . .
F10 C22 C21 117.9(6) . .
C17 C22 C21 122.9(6) . .
C7 C23 C9 105.5(6) . .
C7 C23 C24 107.1(6) . .
C9 C23 C24 118.3(6) . .
C7 C23 H23 108.5 . .
C9 C23 H23 108.5 . .
C24 C23 H23 108.5 . .
N3 C24 C23 99.3(7) . .
N3 C24 H24A 111.9 . .
C23 C24 H24A 111.9 . .
N3 C24 H24B 111.9 . .
C23 C24 H24B 111.9 . .
H24A C24 H24B 109.6 . .
N3 C25 C26 110.6(10) . .
N3 C25 H25A 109.5 . .
C26 C25 H25A 109.5 . .
N3 C25 H25B 109.5 . .
C26 C25 H25B 109.5 . .
H25A C25 H25B 108.1 . .
C27 C26 C31 120.0 . .
C27 C26 C25 117.4(12) . .
C31 C26 C25 122.2(12) . .
C28 C27 C26 120.0 . .
C28 C27 H27 120.0 . .
C26 C27 H27 120.0 . .
C27 C28 C29 120.0 . .
C27 C28 H28 120.0 . .
C29 C28 H28 120.0 . .
C30 C29 C28 120.0 . .
C30 C29 H29 120.0 . .
C28 C29 H29 120.0 . .
C29 C30 C31 120.0 . .
C29 C30 H30 120.0 . .
C31 C30 H30 120.0 . .
C30 C31 C26 120.0 . .
C30 C31 H31 120.0 . .
C26 C31 H31 120.0 . .
N6 O2 C39 109.2(10) . .
C32 N4 C35 110.5(5) . .
C32 N4 H4 124.7 . .
C35 N4 H4 124.7 . .
C40 N5 C37 106.3(5) . .
O2 N6 C54 102.2(11) . .
O2 N6 C55 107.3(13) . .
C54 N6 C55 114.8(16) . .
N4 C32 C41 125.6(6) . .
N4 C32 C33 106.5(6) . .
C41 C32 C33 127.9(6) . .
C34 C33 C32 108.9(6) . .
C34 C33 H33 125.5 . .
C32 C33 H33 125.5 . .
C33 C34 C35 108.9(6) . .
C33 C34 H34 125.6 . .
C35 C34 H34 125.6 . .
C36 C35 N4 126.0(6) . .
C36 C35 C34 128.8(6) . .
N4 C35 C34 105.2(5) . .
C35 C36 C37 128.4(6) . .
C35 C36 C48 116.4(6) . .
C37 C36 C48 115.2(6) . .
C36 C37 N5 123.3(6) . .
C36 C37 C38 124.9(6) . .
N5 C37 C38 111.8(6) . .
C39 C38 C37 104.6(6) . .
C39 C38 C54 102.4(9) . .
C37 C38 C54 116.8(9) . .
C39 C38 H38 110.8 . .
C37 C38 H38 110.8 . .
C54 C38 H38 110.8 . .
O2 C39 C38 108.7(8) . .
O2 C39 C40 111.4(9) . .
C38 C39 C40 104.8(7) . .
O2 C39 H39 110.6 . .
C38 C39 H39 110.6 . .
C40 C39 H39 110.6 . .
N5 C40 C41 125.9(6) . 2_565
N5 C40 C39 112.5(6) . .
C41 C40 C39 121.5(7) 2_565 .
C40 C41 C32 127.5(7) 2_565 .
C40 C41 C42 116.4(6) 2_565 .
C32 C41 C42 116.1(5) . .
C43 C42 C47 120.0 . .
C43 C42 C41 121.1(5) . .
C47 C42 C41 118.9(5) . .
F11 C43 C44 121.5(6) . .
F11 C43 C42 118.5(6) . .
C44 C43 C42 120.0 . .
F12 C44 C45 123.0(9) . .
F12 C44 C43 117.0(9) . .
C45 C44 C43 120.0 . .
F13 C45 C44 117.8(10) . .
F13 C45 C46 122.2(10) . .
C44 C45 C46 120.0 . .
F14 C46 C47 120.3(7) . .
F14 C46 C45 119.7(7) . .
C47 C46 C45 120.0 . .
F15 C47 C46 117.2(6) . .
F15 C47 C42 122.7(6) . .
C46 C47 C42 120.0 . .
C49 C48 C53 117.0(6) . .
C49 C48 C36 121.9(7) . .
C53 C48 C36 121.1(6) . .
F16 C49 C48 120.3(6) . .
F16 C49 C50 117.6(6) . .
C48 C49 C50 122.1(7) . .
C51 C50 F17 122.1(6) . .
C51 C50 C49 119.6(7) . .
F17 C50 C49 118.3(7) . .
C50 C51 F18 121.5(7) . .
C50 C51 C52 121.2(6) . .
F18 C51 C52 117.2(7) . .
F19 C52 C53 121.4(7) . .
F19 C52 C51 121.0(7) . .
C53 C52 C51 117.6(7) . .
F20 C53 C52 117.0(6) . .
F20 C53 C48 120.6(6) . .
C52 C53 C48 122.5(7) . .
N6 C54 C38 105.5(10) . .
N6 C54 H54A 110.6 . .
C38 C54 H54A 110.6 . .
N6 C54 H54B 110.6 . .
C38 C54 H54B 110.6 . .
H54A C54 H54B 108.8 . .
C56 C55 N6 119.9(18) . .
C56 C55 H55A 107.4 . .
N6 C55 H55A 107.4 . .
C56 C55 H55B 107.4 . .
N6 C55 H55B 107.4 . .
H55A C55 H55B 106.9 . .
C55 C56 C57 121.7(14) . .
C55 C56 C61 118.2(14) . .
C57 C56 C61 120.0 . .
C58 C57 C56 120.0 . .
C58 C57 H57 120.0 . .
C56 C57 H57 120.0 . .
C59 C58 C57 120.0 . .
C59 C58 H58 120.0 . .
C57 C58 H58 120.0 . .
C58 C59 C60 120.0 . .
C58 C59 H59 120.0 . .
C60 C59 H59 120.0 . .
C59 C60 C61 120.0 . .
C59 C60 H60 120.0 . .
C61 C60 H60 120.0 . .
C60 C61 C56 120.0 . .
C60 C61 H61 120.0 . .
C56 C61 H61 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C15 1.306(5) .
F2 C14 1.334(5) .
F3 C13 1.337(5) .
F4 C12 1.331(5) .
F5 C11 1.301(5) .
F6 C18 1.322(8) .
F7 C19 1.316(8) .
F8 C20 1.327(8) .
F9 C21 1.337(8) .
F10 C22 1.346(7) .
O1 N3 1.471(15) .
O1 C7 1.588(15) .
N1 C1 1.357(8) .
N1 C4 1.385(8) .
N1 H1 0.8800 .
N2 C9 1.348(8) .
N2 C6 1.379(8) .
N3 C24 1.403(13) .
N3 C25 1.504(15) .
C1 C16 1.396(9) 2_666
C1 C2 1.428(9) .
C2 C3 1.361(9) .
C2 H2 0.9500 .
C3 C4 1.402(9) .
C3 H3 0.9500 .
C4 C5 1.386(9) .
C5 C6 1.407(8) .
C5 C10 1.516(6) .
C6 C7 1.491(9) .
C7 C23 1.413(9) .
C7 H7 1.0000 .
C9 C16 1.410(9) .
C9 C23 1.471(9) .
C10 C11 1.3900 .
C10 C15 1.3900 .
C11 C12 1.3900 .
C12 C13 1.3900 .
C13 C14 1.3900 .
C14 C15 1.3900 .
C16 C1 1.396(9) 2_666
C16 C17 1.496(8) .
C17 C22 1.371(9) .
C17 C18 1.400(9) .
C18 C19 1.380(10) .
C19 C20 1.399(10) .
C20 C21 1.366(11) .
C21 C22 1.382(9) .
C23 C24 1.516(11) .
C23 H23 1.0000 .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C26 1.536(15) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 C27 1.3900 .
C26 C31 1.3900 .
C27 C28 1.3900 .
C27 H27 0.9500 .
C28 C29 1.3900 .
C28 H28 0.9500 .
C29 C30 1.3900 .
C29 H29 0.9500 .
C30 C31 1.3900 .
C30 H30 0.9500 .
C31 H31 0.9500 .
F11 C43 1.332(11) .
F12 C44 1.324(13) .
F13 C45 1.322(7) .
F14 C46 1.370(11) .
F15 C47 1.277(9) .
F16 C49 1.342(8) .
F17 C50 1.349(8) .
F18 C51 1.349(8) .
F19 C52 1.328(9) .
F20 C53 1.349(8) .
O2 N6 1.393(13) .
O2 C39 1.413(14) .
N4 C32 1.356(9) .
N4 C35 1.393(8) .
N4 H4 0.8800 .
N5 C40 1.352(9) .
N5 C37 1.393(8) .
N6 C54 1.476(18) .
N6 C55 1.50(2) .
C32 C41 1.394(10) .
C32 C33 1.427(9) .
C33 C34 1.333(10) .
C33 H33 0.9500 .
C34 C35 1.434(9) .
C34 H34 0.9500 .
C35 C36 1.372(10) .
C36 C37 1.390(10) .
C36 C48 1.521(9) .
C37 C38 1.474(11) .
C38 C39 1.445(11) .
C38 C54 1.53(2) .
C38 H38 1.0000 .
C39 C40 1.482(12) .
C39 H39 1.0000 .
C40 C41 1.383(10) 2_565
C41 C40 1.383(10) 2_565
C41 C42 1.537(8) .
C42 C43 1.3900 .
C42 C47 1.3900 .
C43 C44 1.3900 .
C44 C45 1.3900 .
C45 C46 1.3900 .
C46 C47 1.3900 .
C48 C49 1.343(10) .
C48 C53 1.388(10) .
C49 C50 1.403(9) .
C50 C51 1.322(11) .
C51 C52 1.396(11) .
C52 C53 1.379(10) .
C54 H54A 0.9900 .
C54 H54B 0.9900 .
C55 C56 1.34(2) .
C55 H55A 0.9900 .
C55 H55B 0.9900 .
C56 C57 1.3900 .
C56 C61 1.3900 .
C57 C58 1.3900 .
C57 H57 0.9500 .
C58 C59 1.3900 .
C58 H58 0.9500 .
C59 C60 1.3900 .
C59 H59 0.9500 .
C60 C61 1.3900 .
C60 H60 0.9500 .
C61 H61 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.88 2.42 2.962(7) 120.2 .
N1 H1 N2 0.88 2.36 2.907(7) 120.6 2_666
C2 H2 F18 0.95 2.59 3.236(8) 125.8 1_655
C7 H7 F5 1.00 2.51 3.239(7) 129.5 .
C7 H7 F16 1.00 2.41 3.283(8) 145.1 .
C23 H23 F7 1.00 2.63 3.323(8) 126.7 2_566
C24 H24A F10 0.99 2.60 3.547(10) 159.7 .
N4 H4 N5 0.88 2.37 2.914(8) 120.3 .
N4 H4 N5 0.88 2.39 2.941(7) 120.8 2_565
C33 H33 F3 0.95 2.61 3.209(8) 121.1 .
C55 H55A N1 0.99 2.59 3.438(17) 144.1 1_455
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_4
C7 O1 N3 C24 43.9(10) . .
C7 O1 N3 C25 161.0(11) . .
C4 N1 C1 C16 -175.9(5) . 2_666
C4 N1 C1 C2 0.3(7) . .
N1 C1 C2 C3 0.3(7) . .
C16 C1 C2 C3 176.5(6) 2_666 .
C1 C2 C3 C4 -0.8(7) . .
C1 N1 C4 C5 179.0(6) . .
C1 N1 C4 C3 -0.8(6) . .
C2 C3 C4 N1 1.0(7) . .
C2 C3 C4 C5 -178.8(6) . .
N1 C4 C5 C6 0.3(10) . .
C3 C4 C5 C6 -179.9(6) . .
N1 C4 C5 C10 -177.1(5) . .
C3 C4 C5 C10 2.7(9) . .
C9 N2 C6 C5 177.8(5) . .
C9 N2 C6 C7 -1.0(6) . .
C4 C5 C6 N2 2.6(10) . .
C10 C5 C6 N2 180.0(5) . .
C4 C5 C6 C7 -178.8(6) . .
C10 C5 C6 C7 -1.4(8) . .
N2 C6 C7 C23 3.4(7) . .
C5 C6 C7 C23 -175.3(6) . .
N2 C6 C7 O1 -113.6(7) . .
C5 C6 C7 O1 67.6(8) . .
N3 O1 C7 C23 -20.7(10) . .
N3 O1 C7 C6 95.2(9) . .
C6 N2 C9 C16 178.1(6) . .
C6 N2 C9 C23 -1.8(6) . .
C4 C5 C10 C11 -111.3(5) . .
C6 C5 C10 C11 71.0(6) . .
C4 C5 C10 C15 70.6(6) . .
C6 C5 C10 C15 -107.1(5) . .
C15 C10 C11 F5 -179.0(4) . .
C5 C10 C11 F5 2.9(5) . .
C15 C10 C11 C12 0.0 . .
C5 C10 C11 C12 -178.1(4) . .
F5 C11 C12 F4 -1.2(5) . .
C10 C11 C12 F4 179.8(4) . .
F5 C11 C12 C13 179.0(4) . .
C10 C11 C12 C13 0.0 . .
F4 C12 C13 F3 0.0(5) . .
C11 C12 C13 F3 179.8(4) . .
F4 C12 C13 C14 -179.8(4) . .
C11 C12 C13 C14 0.0 . .
F3 C13 C14 F2 2.6(5) . .
C12 C13 C14 F2 -177.6(5) . .
F3 C13 C14 C15 -179.8(4) . .
C12 C13 C14 C15 0.0 . .
F2 C14 C15 F1 -3.5(5) . .
C13 C14 C15 F1 178.9(4) . .
F2 C14 C15 C10 177.6(5) . .
C13 C14 C15 C10 0.0 . .
C11 C10 C15 F1 -178.9(5) . .
C5 C10 C15 F1 -0.7(5) . .
C11 C10 C15 C14 0.0 . .
C5 C10 C15 C14 178.2(4) . .
N2 C9 C16 C1 -4.2(9) . 2_666
C23 C9 C16 C1 175.7(6) . 2_666
N2 C9 C16 C17 175.3(5) . .
C23 C9 C16 C17 -4.8(8) . .
C1 C16 C17 C22 -74.3(8) 2_666 .
C9 C16 C17 C22 106.1(7) . .
C1 C16 C17 C18 102.6(7) 2_666 .
C9 C16 C17 C18 -77.0(7) . .
C22 C17 C18 F6 178.4(6) . .
C16 C17 C18 F6 1.3(9) . .
C22 C17 C18 C19 -1.7(10) . .
C16 C17 C18 C19 -178.8(7) . .
F6 C18 C19 F7 0.9(11) . .
C17 C18 C19 F7 -179.0(7) . .
F6 C18 C19 C20 -178.1(7) . .
C17 C18 C19 C20 2.0(11) . .
F7 C19 C20 F8 -1.0(11) . .
C18 C19 C20 F8 177.9(7) . .
F7 C19 C20 C21 179.8(7) . .
C18 C19 C20 C21 -1.2(11) . .
F8 C20 C21 F9 -0.7(11) . .
C19 C20 C21 F9 178.4(6) . .
F8 C20 C21 C22 -179.0(6) . .
C19 C20 C21 C22 0.1(11) . .
C18 C17 C22 F10 -179.2(6) . .
C16 C17 C22 F10 -2.2(9) . .
C18 C17 C22 C21 0.5(10) . .
C16 C17 C22 C21 177.5(6) . .
F9 C21 C22 F10 1.7(10) . .
C20 C21 C22 F10 180.0(6) . .
F9 C21 C22 C17 -178.0(6) . .
C20 C21 C22 C17 0.2(11) . .
C6 C7 C23 C9 -4.2(6) . .
O1 C7 C23 C9 120.3(7) . .
C6 C7 C23 C24 -131.1(6) . .
O1 C7 C23 C24 -6.6(8) . .
N2 C9 C23 C7 4.0(7) . .
C16 C9 C23 C7 -175.9(5) . .
N2 C9 C23 C24 123.8(6) . .
C16 C9 C23 C24 -56.1(9) . .
O1 N3 C24 C23 -48.9(10) . .
C25 N3 C24 C23 -166.4(9) . .
C7 C23 C24 N3 32.9(9) . .
C9 C23 C24 N3 -86.1(8) . .
C24 N3 C25 C26 -64.0(16) . .
O1 N3 C25 C26 179.7(12) . .
N3 C25 C26 C27 -105.3(13) . .
N3 C25 C26 C31 82.2(15) . .
C31 C26 C27 C28 0.0 . .
C25 C26 C27 C28 -172.7(10) . .
C26 C27 C28 C29 0.0 . .
C27 C28 C29 C30 0.0 . .
C28 C29 C30 C31 0.0 . .
C29 C30 C31 C26 0.0 . .
C27 C26 C31 C30 0.0 . .
C25 C26 C31 C30 172.3(11) . .
C39 O2 N6 C54 -34.3(15) . .
C39 O2 N6 C55 86.8(16) . .
C35 N4 C32 C41 -179.7(7) . .
C35 N4 C32 C33 0.5(8) . .
N4 C32 C33 C34 -0.6(8) . .
C41 C32 C33 C34 179.6(7) . .
C32 C33 C34 C35 0.4(8) . .
C32 N4 C35 C36 -179.5(7) . .
C32 N4 C35 C34 -0.2(7) . .
C33 C34 C35 C36 179.1(7) . .
C33 C34 C35 N4 -0.1(8) . .
N4 C35 C36 C37 -1.1(12) . .
C34 C35 C36 C37 179.8(8) . .
N4 C35 C36 C48 178.8(6) . .
C34 C35 C36 C48 -0.3(11) . .
C35 C36 C37 N5 0.7(13) . .
C48 C36 C37 N5 -179.2(7) . .
C35 C36 C37 C38 177.4(8) . .
C48 C36 C37 C38 -2.5(12) . .
C40 N5 C37 C36 179.4(8) . .
C40 N5 C37 C38 2.3(9) . .
C36 C37 C38 C39 -179.5(9) . .
N5 C37 C38 C39 -2.5(10) . .
C36 C37 C38 C54 -67.1(13) . .
N5 C37 C38 C54 109.9(10) . .
N6 O2 C39 C38 23.1(13) . .
N6 O2 C39 C40 138.1(10) . .
C37 C38 C39 O2 120.8(9) . .
C54 C38 C39 O2 -1.5(12) . .
C37 C38 C39 C40 1.6(10) . .
C54 C38 C39 C40 -120.7(10) . .
C37 N5 C40 C41 177.0(8) . 2_565
C37 N5 C40 C39 -1.2(10) . .
O2 C39 C40 N5 -117.7(9) . .
C38 C39 C40 N5 -0.3(11) . .
O2 C39 C40 C41 64.0(12) . 2_565
C38 C39 C40 C41 -178.6(8) . 2_565
N4 C32 C41 C40 2.9(13) . 2_565
C33 C32 C41 C40 -177.3(8) . 2_565
N4 C32 C41 C42 -177.3(7) . .
C33 C32 C41 C42 2.5(11) . .
C40 C41 C42 C43 93.1(8) 2_565 .
C32 C41 C42 C43 -86.8(7) . .
C40 C41 C42 C47 -86.1(8) 2_565 .
C32 C41 C42 C47 94.0(7) . .
C47 C42 C43 F11 -179.6(7) . .
C41 C42 C43 F11 1.2(7) . .
C47 C42 C43 C44 0.0 . .
C41 C42 C43 C44 -179.2(5) . .
F11 C43 C44 F12 2.3(8) . .
C42 C43 C44 F12 -177.2(7) . .
F11 C43 C44 C45 179.5(8) . .
C42 C43 C44 C45 0.0 . .
F12 C44 C45 F13 -2.4(8) . .
C43 C44 C45 F13 -179.5(7) . .
F12 C44 C45 C46 177.1(8) . .
C43 C44 C45 C46 0.0 . .
F13 C45 C46 F14 2.3(8) . .
C44 C45 C46 F14 -177.2(7) . .
F13 C45 C46 C47 179.5(7) . .
C44 C45 C46 C47 0.0 . .
F14 C46 C47 F15 -0.9(7) . .
C45 C46 C47 F15 -178.1(6) . .
F14 C46 C47 C42 177.2(7) . .
C45 C46 C47 C42 0.0 . .
C43 C42 C47 F15 178.0(7) . .
C41 C42 C47 F15 -2.8(7) . .
C43 C42 C47 C46 0.0 . .
C41 C42 C47 C46 179.2(5) . .
C35 C36 C48 C49 -74.9(9) . .
C37 C36 C48 C49 105.0(8) . .
C35 C36 C48 C53 106.7(8) . .
C37 C36 C48 C53 -73.4(9) . .
C53 C48 C49 F16 179.0(6) . .
C36 C48 C49 F16 0.6(10) . .
C53 C48 C49 C50 0.4(10) . .
C36 C48 C49 C50 -178.0(6) . .
F16 C49 C50 C51 -179.9(7) . .
C48 C49 C50 C51 -1.2(11) . .
F16 C49 C50 F17 0.1(10) . .
C48 C49 C50 F17 178.8(6) . .
F17 C50 C51 F18 -0.6(11) . .
C49 C50 C51 F18 179.4(6) . .
F17 C50 C51 C52 -178.3(6) . .
C49 C50 C51 C52 1.7(10) . .
C50 C51 C52 F19 179.2(7) . .
F18 C51 C52 F19 1.4(9) . .
C50 C51 C52 C53 -1.4(10) . .
F18 C51 C52 C53 -179.2(6) . .
F19 C52 C53 F20 0.2(9) . .
C51 C52 C53 F20 -179.2(6) . .
F19 C52 C53 C48 180.0(6) . .
C51 C52 C53 C48 0.5(10) . .
C49 C48 C53 F20 179.7(6) . .
C36 C48 C53 F20 -1.9(10) . .
C49 C48 C53 C52 -0.1(10) . .
C36 C48 C53 C52 178.4(6) . .
O2 N6 C54 C38 32.2(16) . .
C55 N6 C54 C38 -83.6(16) . .
C39 C38 C54 N6 -18.9(14) . .
C37 C38 C54 N6 -132.5(11) . .
O2 N6 C55 C56 54(2) . .
C54 N6 C55 C56 167.1(17) . .
N6 C55 C56 C57 55(2) . .
N6 C55 C56 C61 -121.6(18) . .
C55 C56 C57 C58 -176.4(10) . .
C61 C56 C57 C58 0.0 . .
C56 C57 C58 C59 0.0 . .
C57 C58 C59 C60 0.0 . .
C58 C59 C60 C61 0.0 . .
C59 C60 C61 C56 0.0 . .
C55 C56 C61 C60 176.6(10) . .
C57 C56 C61 C60 0.0 . .
