#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/90/4309086.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_4309086
loop_
_publ_author_name
'Anna Berlicka'
'Lechosław Latos-Grażyński'
'Tadeusz Lis'
_publ_section_title
;
1H NMR Investigation of High-Spin and Low-Spin
Iron(III)meso-Ethynylporphyrins
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4522
_journal_page_last               4533
_journal_paper_doi               10.1021/ic050158q
_journal_volume                  44
_journal_year                    2005
_chemical_formula_moiety
'C52 H32 N4, C1.73 H1.27 Cl0.54 F2.20 O1.46, 2(C2 H F3 O2), 2(C2 F3 O2)'
_chemical_formula_sum            'C61.73 H35.27 Cl0.54 F14.2 N4 O9.46'
_chemical_formula_weight         1273.27
_chemical_name_systematic
;
5,10,15,20-tetra(phenylethynyl)porphyrin dication
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.81(3)
_cell_angle_beta                 97.36(3)
_cell_angle_gamma                110.75(3)
_cell_formula_units_Z            2
_cell_length_a                   10.454(2)
_cell_length_b                   14.450(4)
_cell_length_c                   20.164(4)
_cell_measurement_reflns_used    13822
_cell_measurement_temperature    100(2)
_cell_volume                     2789.4(13)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 1995-2003)'
_computing_data_collection
'CrysAlis CCD (Oxford Diffraction, 1995-2003)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 1995-2003)'
_computing_molecular_graphics    'XP (Bruker, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'KUMA KM4 CCD κ-geometry diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26076
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1293
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     992
_refine_ls_number_reflns         12767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0850P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1685
_reflns_number_gt                8746
_reflns_number_total             12767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic050158qsi20050131_110352_1.cif
_cod_data_source_block           dication
_cod_original_cell_volume        2789.4(11)
_cod_original_formula_sum        'C61.73 H35.27 Cl0.54 F14.20 N4 O9.46'
_cod_database_code               4309086
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N21 N 0.50003(17) 0.64964(12) 0.75476(9) 0.0210(4) Uani 1 1 d . . .
H21 H 0.581(3) 0.6480(19) 0.7687(13) 0.035(7) Uiso 1 1 d . . .
N22 N 0.76342(17) 0.82938(13) 0.76412(9) 0.0224(4) Uani 1 1 d . . .
H22 H 0.722(3) 0.788(2) 0.7241(14) 0.039(7) Uiso 1 1 d . . .
N23 N 0.89350(17) 0.69617(13) 0.69980(9) 0.0219(4) Uani 1 1 d . . .
H23 H 0.845(3) 0.681(2) 0.7338(14) 0.042(8) Uiso 1 1 d . . .
N24 N 0.61856(17) 0.52157(14) 0.67508(9) 0.0220(4) Uani 1 1 d . . .
H24 H 0.626(3) 0.581(2) 0.6665(14) 0.045(8) Uiso 1 1 d . . .
C1 C 0.3846(2) 0.56428(15) 0.73153(10) 0.0229(4) Uani 1 1 d . . .
C2 C 0.2667(2) 0.58971(17) 0.73790(11) 0.0267(5) Uani 1 1 d . . .
H2 H 0.180(3) 0.5471(17) 0.7257(11) 0.024(6) Uiso 1 1 d . . .
C3 C 0.3124(2) 0.68776(17) 0.76580(12) 0.0279(5) Uani 1 1 d . . .
H3 H 0.260(3) 0.7282(18) 0.7743(12) 0.035(7) Uiso 1 1 d . . .
C4 C 0.4602(2) 0.72615(15) 0.77717(10) 0.0229(4) Uani 1 1 d . . .
C5 C 0.5499(2) 0.82403(16) 0.80734(11) 0.0241(4) Uani 1 1 d . . .
C6 C 0.6931(2) 0.86840(15) 0.80461(11) 0.0238(4) Uani 1 1 d . . .
C7 C 0.7900(2) 0.95998(17) 0.84385(12) 0.0298(5) Uani 1 1 d . . .
H7 H 0.767(2) 0.9984(17) 0.8764(12) 0.023(6) Uiso 1 1 d . . .
C8 C 0.9164(2) 0.97446(17) 0.82645(12) 0.0300(5) Uani 1 1 d . . .
H8 H 1.002(3) 1.030(2) 0.8438(13) 0.040(7) Uiso 1 1 d . . .
C9 C 0.9007(2) 0.89251(15) 0.77617(11) 0.0244(4) Uani 1 1 d . . .
C10 C 1.0061(2) 0.87791(16) 0.74438(11) 0.0240(4) Uani 1 1 d . . .
C11 C 0.9964(2) 0.78895(15) 0.70445(11) 0.0227(4) Uani 1 1 d . . .
C12 C 1.0897(2) 0.77762(17) 0.66137(11) 0.0260(5) Uani 1 1 d . . .
H12 H 1.165(3) 0.8316(19) 0.6540(12) 0.031(6) Uiso 1 1 d . . .
C13 C 1.0438(2) 0.67940(17) 0.63275(11) 0.0245(4) Uani 1 1 d . . .
H13 H 1.081(3) 0.6526(19) 0.6038(13) 0.036(7) Uiso 1 1 d . . .
C14 C 0.9192(2) 0.62732(15) 0.65684(10) 0.0228(4) Uani 1 1 d . . .
C15 C 0.8393(2) 0.52383(15) 0.64139(10) 0.0225(4) Uani 1 1 d . . .
C16 C 0.7057(2) 0.47539(15) 0.65639(10) 0.0219(4) Uani 1 1 d . . .
C17 C 0.6381(2) 0.37116(16) 0.65709(11) 0.0256(4) Uani 1 1 d . . .
H17 H 0.679(3) 0.3194(19) 0.6489(13) 0.039(7) Uiso 1 1 d . . .
C18 C 0.5140(2) 0.35634(16) 0.67664(11) 0.0254(4) Uani 1 1 d . . .
H18 H 0.451(2) 0.2977(17) 0.6846(11) 0.024(6) Uiso 1 1 d . . .
C19 C 0.5002(2) 0.45095(15) 0.68771(10) 0.0225(4) Uani 1 1 d . . .
C20 C 0.3855(2) 0.46958(15) 0.70794(10) 0.0223(4) Uani 1 1 d . . .
C25 C 0.4901(2) 0.88201(16) 0.84465(11) 0.0275(5) Uani 1 1 d . . .
C26 C 0.4364(2) 0.92621(17) 0.87778(12) 0.0283(5) Uani 1 1 d . . .
C27 C 0.3675(2) 0.97602(17) 0.91700(11) 0.0296(5) Uani 1 1 d . . .
C28 C 0.2324(3) 0.9239(2) 0.92647(14) 0.0417(6) Uani 1 1 d . . .
H28 H 0.183(3) 0.853(2) 0.9063(16) 0.057(9) Uiso 1 1 d . . .
C29 C 0.1654(3) 0.9728(3) 0.96278(16) 0.0553(8) Uani 1 1 d . . .
H29 H 0.071(4) 0.938(3) 0.971(2) 0.090(12) Uiso 1 1 d . . .
C30 C 0.2294(4) 1.0717(3) 0.98956(15) 0.0541(8) Uani 1 1 d . . .
H30 H 0.177(4) 1.110(3) 1.0153(17) 0.074(10) Uiso 1 1 d . . .
C31 C 0.3618(4) 1.1233(2) 0.98106(14) 0.0532(8) Uani 1 1 d . . .
H31 H 0.417(4) 1.190(3) 0.9974(19) 0.084(12) Uiso 1 1 d . . .
C32 C 0.4336(3) 1.07692(19) 0.94543(13) 0.0385(6) Uani 1 1 d . . .
H32 H 0.524(3) 1.1059(18) 0.9375(12) 0.031(6) Uiso 1 1 d . . .
C33 C 1.1337(2) 0.96156(16) 0.75443(11) 0.0264(5) Uani 1 1 d . . .
C34 C 1.2390(2) 1.03454(16) 0.76664(11) 0.0269(5) Uani 1 1 d . . .
C35 C 1.3615(2) 1.12389(16) 0.78724(11) 0.0274(5) Uani 1 1 d . . .
C36 C 1.3487(3) 1.21085(17) 0.81699(12) 0.0320(5) Uani 1 1 d . . .
H36 H 1.262(3) 1.2180(18) 0.8208(12) 0.033(6) Uiso 1 1 d . . .
C37 C 1.4658(3) 1.29476(19) 0.84343(13) 0.0392(6) Uani 1 1 d . . .
H37 H 1.451(3) 1.350(2) 0.8623(16) 0.059(9) Uiso 1 1 d . . .
C38 C 1.5959(3) 1.2921(2) 0.84067(13) 0.0423(6) Uani 1 1 d . . .
H38 H 1.684(3) 1.351(2) 0.8614(15) 0.056(8) Uiso 1 1 d . . .
C39 C 1.6096(3) 1.2073(2) 0.81012(13) 0.0387(6) Uani 1 1 d . . .
H39 H 1.700(3) 1.2007(19) 0.8103(13) 0.043(7) Uiso 1 1 d . . .
C40 C 1.4925(2) 1.12255(19) 0.78275(12) 0.0325(5) Uani 1 1 d . . .
H40 H 1.502(2) 1.0638(19) 0.7652(12) 0.032(7) Uiso 1 1 d . . .
C41 C 0.8995(2) 0.46191(15) 0.60796(11) 0.0236(4) Uani 1 1 d . . .
C42 C 0.9509(2) 0.41083(16) 0.57971(11) 0.0239(4) Uani 1 1 d . . .
C43 C 1.0189(2) 0.35293(16) 0.54747(10) 0.0236(4) Uani 1 1 d . . .
C44 C 1.1506(2) 0.40209(17) 0.53244(11) 0.0268(5) Uani 1 1 d . . .
H44 H 1.193(3) 0.4757(19) 0.5425(12) 0.035(7) Uiso 1 1 d . . .
C45 C 1.2201(2) 0.34803(18) 0.50332(13) 0.0328(5) Uani 1 1 d . . .
H45 H 1.313(2) 0.3828(15) 0.4923(11) 0.018(5) Uiso 1 1 d . . .
C46 C 1.1600(2) 0.24428(18) 0.48920(13) 0.0337(5) Uani 1 1 d . . .
H46 H 1.204(2) 0.2044(17) 0.4658(12) 0.029(6) Uiso 1 1 d . . .
C47 C 1.0294(3) 0.19533(18) 0.50376(12) 0.0329(5) Uani 1 1 d . . .
H47 H 0.985(3) 0.120(2) 0.4950(13) 0.039(7) Uiso 1 1 d . . .
C48 C 0.9579(2) 0.24818(17) 0.53251(11) 0.0286(5) Uani 1 1 d . . .
H48 H 0.867(3) 0.2102(19) 0.5438(13) 0.041(7) Uiso 1 1 d . . .
C49 C 0.2615(2) 0.38520(16) 0.70458(11) 0.0242(4) Uani 1 1 d . . .
C50 C 0.1565(2) 0.31387(16) 0.70109(11) 0.0256(4) Uani 1 1 d . . .
C51 C 0.0331(2) 0.22551(16) 0.69082(11) 0.0257(4) Uani 1 1 d . . .
C52 C 0.0386(2) 0.13331(17) 0.66692(12) 0.0312(5) Uani 1 1 d . . .
H52 H 0.120(3) 0.1269(19) 0.6605(14) 0.041(7) Uiso 1 1 d . . .
C53 C -0.0812(3) 0.04861(19) 0.65150(13) 0.0382(6) Uani 1 1 d . . .
H53 H -0.077(3) -0.016(2) 0.6354(13) 0.036(7) Uiso 1 1 d . . .
C54 C -0.2070(3) 0.0543(2) 0.65971(14) 0.0405(6) Uani 1 1 d . . .
H54 H -0.293(3) -0.009(2) 0.6479(15) 0.059(9) Uiso 1 1 d . . .
C55 C -0.2143(2) 0.1451(2) 0.68344(13) 0.0400(6) Uani 1 1 d . . .
H55 H -0.303(3) 0.1526(18) 0.6884(13) 0.035(7) Uiso 1 1 d . . .
C56 C -0.0942(2) 0.23128(19) 0.69973(12) 0.0304(5) Uani 1 1 d . . .
H56 H -0.101(2) 0.2890(19) 0.7158(12) 0.030(6) Uiso 1 1 d . . .
C1A C 0.5438(2) 0.74097(15) 0.61636(11) 0.0226(4) Uani 1 1 d . . .
C2A C 0.4433(2) 0.68050(16) 0.55103(11) 0.0265(5) Uani 1 1 d . . .
O1A O 0.63298(14) 0.70774(11) 0.63878(7) 0.0246(3) Uani 1 1 d . . .
O2A O 0.52750(16) 0.81705(11) 0.64092(8) 0.0335(4) Uani 1 1 d . . .
F1A F 0.43685(14) 0.58603(10) 0.53998(8) 0.0427(4) Uani 1 1 d . . .
F2A F 0.31487(13) 0.67686(11) 0.55216(8) 0.0455(4) Uani 1 1 d . . .
F3A F 0.48409(16) 0.72137(12) 0.49751(7) 0.0481(4) Uani 1 1 d . . .
C1B C 0.7806(2) 0.59224(16) 0.85123(11) 0.0259(5) Uani 1 1 d . . .
C2B C 0.9222(2) 0.58109(18) 0.85638(12) 0.0318(5) Uani 1 1 d . . .
O1B O 0.75406(14) 0.64035(11) 0.80741(7) 0.0254(3) Uani 1 1 d . . .
O2B O 0.7025(2) 0.5432(2) 0.88839(12) 0.0329(7) Uani 0.896(8) 1 d P . .
O2B0 O 0.7436(17) 0.5937(16) 0.9078(8) 0.017(4) Uiso 0.104(8) 1 d P . .
F1B F 0.96589(15) 0.56241(12) 0.91595(8) 0.0463(4) Uani 1 1 d . . .
F2B F 1.02011(14) 0.66229(12) 0.84359(8) 0.0478(4) Uani 1 1 d . . .
F3B F 0.91217(16) 0.50479(12) 0.80955(8) 0.0519(4) Uani 1 1 d . . .
C1C C 0.4465(3) 0.58493(18) 0.94113(14) 0.0364(6) Uani 1 1 d . . .
C2C C 0.3021(3) 0.5904(2) 0.93675(14) 0.0398(6) Uani 1 1 d . . .
O1C O 0.4698(2) 0.5505(3) 0.88393(11) 0.0379(8) Uani 0.896(8) 1 d P . .
O1C0 O 0.499(2) 0.606(2) 0.9001(11) 0.038(6) Uiso 0.104(8) 1 d P . .
H1C H 0.568(5) 0.557(4) 0.887(2) 0.126(17) Uiso 1 1 d . . .
O2C O 0.5256(2) 0.61510(18) 0.99447(11) 0.0643(6) Uani 1 1 d . . .
F1C F 0.31191(17) 0.68390(12) 0.92961(9) 0.0549(4) Uani 1 1 d . . .
F2C F 0.25009(16) 0.56915(13) 0.99220(8) 0.0535(4) Uani 1 1 d . . .
F3C F 0.21189(15) 0.52935(13) 0.88381(8) 0.0517(4) Uani 1 1 d . . .
C1D C 0.3796(2) 0.95531(17) 0.55859(12) 0.0295(5) Uani 1 1 d . . .
C2D C 0.3356(3) 1.04597(18) 0.55900(13) 0.0364(6) Uani 1 1 d . . .
O1D O 0.41150(18) 0.94150(14) 0.62018(9) 0.0386(4) Uani 1 1 d . . .
H1D H 0.440(4) 0.892(3) 0.6162(19) 0.082(12) Uiso 1 1 d . . .
O2D O 0.37789(18) 0.90660(13) 0.50624(9) 0.0398(4) Uani 1 1 d . . .
F1D F 0.43110(17) 1.12789(10) 0.59676(8) 0.0486(4) Uani 1 1 d . . .
F2D F 0.21881(16) 1.02684(12) 0.58513(10) 0.0581(5) Uani 1 1 d . . .
F3D F 0.31060(18) 1.06603(12) 0.49734(8) 0.0552(4) Uani 1 1 d . . .
C1F C 0.8847(3) 0.7072(2) 1.02469(19) 0.0338(8) Uani 0.732(3) 1 d P A 1
C2F C 1.0206(4) 0.7245(3) 1.0716(2) 0.0416(9) Uani 0.732(3) 1 d P A 1
O1F O 0.7792(3) 0.65422(19) 1.04951(13) 0.0421(7) Uani 0.732(3) 1 d P A 1
H1F H 0.666(7) 0.627(4) 1.023(3) 0.12(2) Uiso 0.732(3) 1 d P A 1
O2F O 0.8850(3) 0.74306(18) 0.97282(13) 0.0435(7) Uani 0.732(3) 1 d P A 1
F1F F 1.0306(2) 0.64394(18) 1.08867(16) 0.0765(10) Uani 0.732(3) 1 d P A 1
F2F F 1.1289(3) 0.7676(3) 1.04282(17) 0.0864(11) Uani 0.732(3) 1 d P A 1
F3F F 1.0349(4) 0.7884(3) 1.12601(18) 0.0955(13) Uani 0.732(3) 1 d P A 1
Cl1 Cl 0.9642(4) 0.7212(3) 1.13786(15) 0.0622(11) Uani 0.268(3) 1 d P A 2
Cl2 Cl 1.0268(7) 0.7751(3) 1.0093(3) 0.106(2) Uani 0.268(3) 1 d P A 2
C57 C 0.9273(18) 0.6823(12) 1.0513(8) 0.072(4) Uiso 0.268(3) 1 d P A 2
H57A H 0.8274 0.6663 1.0347 0.086 Uiso 0.268(3) 1 calc PR A 2
H57B H 0.9467 0.6207 1.0410 0.086 Uiso 0.268(3) 1 calc PR A 2
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C4 N21 C1 109.56(17) . . ?
C4 N21 H21 123.2(17) . . ?
C1 N21 H21 122.4(17) . . ?
C6 N22 C9 108.83(18) . . ?
C6 N22 H22 123.2(16) . . ?
C9 N22 H22 122.1(17) . . ?
C14 N23 C11 109.53(18) . . ?
C14 N23 H23 124.1(17) . . ?
C11 N23 H23 120.5(17) . . ?
C19 N24 C16 109.15(17) . . ?
C19 N24 H24 124.6(18) . . ?
C16 N24 H24 123.1(19) . . ?
N21 C1 C20 125.52(18) . . ?
N21 C1 C2 107.06(18) . . ?
C20 C1 C2 127.39(19) . . ?
C3 C2 C1 108.16(19) . . ?
C3 C2 H2 127.7(15) . . ?
C1 C2 H2 124.1(15) . . ?
C2 C3 C4 107.94(19) . . ?
C2 C3 H3 128.9(15) . . ?
C4 C3 H3 123.0(15) . . ?
N21 C4 C5 126.00(18) . . ?
N21 C4 C3 107.26(18) . . ?
C5 C4 C3 126.72(19) . . ?
C4 C5 C6 125.97(19) . . ?
C4 C5 C25 116.32(19) . . ?
C6 C5 C25 117.70(19) . . ?
N22 C6 C5 125.53(19) . . ?
N22 C6 C7 107.96(18) . . ?
C5 C6 C7 126.5(2) . . ?
C8 C7 C6 107.6(2) . . ?
C8 C7 H7 128.7(15) . . ?
C6 C7 H7 123.7(14) . . ?
C7 C8 C9 108.1(2) . . ?
C7 C8 H8 127.5(16) . . ?
C9 C8 H8 124.4(16) . . ?
N22 C9 C10 125.76(19) . . ?
N22 C9 C8 107.57(19) . . ?
C10 C9 C8 126.7(2) . . ?
C11 C10 C9 126.21(19) . . ?
C11 C10 C33 117.85(19) . . ?
C9 C10 C33 115.94(19) . . ?
N23 C11 C10 125.87(19) . . ?
N23 C11 C12 107.05(18) . . ?
C10 C11 C12 127.08(19) . . ?
C13 C12 C11 108.38(19) . . ?
C13 C12 H12 128.8(15) . . ?
C11 C12 H12 122.7(15) . . ?
C12 C13 C14 107.6(2) . . ?
C12 C13 H13 126.9(17) . . ?
C14 C13 H13 125.5(17) . . ?
N23 C14 C15 125.99(19) . . ?
N23 C14 C13 107.42(18) . . ?
C15 C14 C13 126.6(2) . . ?
C14 C15 C16 126.14(19) . . ?
C14 C15 C41 117.04(18) . . ?
C16 C15 C41 116.82(19) . . ?
N24 C16 C15 125.78(19) . . ?
N24 C16 C17 107.38(18) . . ?
C15 C16 C17 126.82(19) . . ?
C18 C17 C16 108.06(19) . . ?
C18 C17 H17 126.1(15) . . ?
C16 C17 H17 125.6(15) . . ?
C17 C18 C19 108.0(2) . . ?
C17 C18 H18 127.6(14) . . ?
C19 C18 H18 124.3(14) . . ?
N24 C19 C20 125.84(19) . . ?
N24 C19 C18 107.45(18) . . ?
C20 C19 C18 126.71(19) . . ?
C1 C20 C19 125.61(19) . . ?
C1 C20 C49 117.34(18) . . ?
C19 C20 C49 117.04(19) . . ?
C26 C25 C5 176.3(2) . . ?
C25 C26 C27 177.9(2) . . ?
C28 C27 C32 119.2(2) . . ?
C28 C27 C26 120.0(2) . . ?
C32 C27 C26 120.8(2) . . ?
C29 C28 C27 119.7(3) . . ?
C29 C28 H28 119.6(18) . . ?
C27 C28 H28 120.7(18) . . ?
C30 C29 C28 120.9(3) . . ?
C30 C29 H29 117(2) . . ?
C28 C29 H29 122(2) . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 118.9(19) . . ?
C29 C30 H30 121.2(19) . . ?
C30 C31 C32 121.2(3) . . ?
C30 C31 H31 128(2) . . ?
C32 C31 H31 111(2) . . ?
C31 C32 C27 119.1(3) . . ?
C31 C32 H32 127.1(15) . . ?
C27 C32 H32 113.8(15) . . ?
C34 C33 C10 175.7(2) . . ?
C33 C34 C35 174.7(2) . . ?
C40 C35 C36 119.9(2) . . ?
C40 C35 C34 121.0(2) . . ?
C36 C35 C34 118.9(2) . . ?
C37 C36 C35 120.1(2) . . ?
C37 C36 H36 115.2(15) . . ?
C35 C36 H36 124.7(15) . . ?
C36 C37 C38 119.7(3) . . ?
C36 C37 H37 116(2) . . ?
C38 C37 H37 124(2) . . ?
C39 C38 C37 120.6(2) . . ?
C39 C38 H38 117.6(17) . . ?
C37 C38 H38 121.8(17) . . ?
C38 C39 C40 120.3(2) . . ?
C38 C39 H39 122.9(16) . . ?
C40 C39 H39 116.5(16) . . ?
C39 C40 C35 119.3(2) . . ?
C39 C40 H40 120.1(16) . . ?
C35 C40 H40 120.4(16) . . ?
C42 C41 C15 179.3(2) . . ?
C41 C42 C43 177.3(2) . . ?
C44 C43 C48 119.4(2) . . ?
C44 C43 C42 119.10(19) . . ?
C48 C43 C42 121.50(19) . . ?
C45 C44 C43 120.3(2) . . ?
C45 C44 H44 120.6(15) . . ?
C43 C44 H44 119.1(15) . . ?
C44 C45 C46 120.1(2) . . ?
C44 C45 H45 120.2(12) . . ?
C46 C45 H45 119.6(12) . . ?
C47 C46 C45 119.7(2) . . ?
C47 C46 H46 118.2(14) . . ?
C45 C46 H46 121.8(14) . . ?
C48 C47 C46 120.9(2) . . ?
C48 C47 H47 118.4(15) . . ?
C46 C47 H47 120.6(15) . . ?
C47 C48 C43 119.5(2) . . ?
C47 C48 H48 118.2(15) . . ?
C43 C48 H48 122.2(15) . . ?
C50 C49 C20 179.4(2) . . ?
C49 C50 C51 174.7(2) . . ?
C52 C51 C56 119.6(2) . . ?
C52 C51 C50 119.2(2) . . ?
C56 C51 C50 121.0(2) . . ?
C53 C52 C51 120.1(2) . . ?
C53 C52 H52 118.0(17) . . ?
C51 C52 H52 121.9(17) . . ?
C54 C53 C52 120.4(3) . . ?
C54 C53 H53 119.4(15) . . ?
C52 C53 H53 120.2(15) . . ?
C53 C54 C55 120.2(2) . . ?
C53 C54 H54 119.0(18) . . ?
C55 C54 H54 120.7(17) . . ?
C54 C55 C56 120.2(2) . . ?
C54 C55 H55 122.6(15) . . ?
C56 C55 H55 117.2(15) . . ?
C55 C56 C51 119.5(2) . . ?
C55 C56 H56 118.5(16) . . ?
C51 C56 H56 122.0(16) . . ?
O2A C1A O1A 127.1(2) . . ?
O2A C1A C2A 116.58(18) . . ?
O1A C1A C2A 116.32(18) . . ?
F3A C2A F2A 107.58(18) . . ?
F3A C2A F1A 106.61(18) . . ?
F2A C2A F1A 107.34(17) . . ?
F3A C2A C1A 110.64(17) . . ?
F2A C2A C1A 111.90(18) . . ?
F1A C2A C1A 112.48(17) . . ?
O1B C1B O2B0 124.1(7) . . ?
O1B C1B O2B 128.8(2) . . ?
O2B0 C1B O2B 34.3(9) . . ?
O1B C1B C2B 116.33(19) . . ?
O2B0 C1B C2B 110.8(7) . . ?
O2B C1B C2B 114.51(19) . . ?
F1B C2B F2B 108.05(19) . . ?
F1B C2B F3B 107.7(2) . . ?
F2B C2B F3B 106.6(2) . . ?
F1B C2B C1B 113.3(2) . . ?
F2B C2B C1B 111.86(19) . . ?
F3B C2B C1B 109.05(18) . . ?
O2B0 O2B C1B 72.3(11) . . ?
O2B O2B0 C1B 73.5(13) . . ?
O1C0 C1C O2C 111.2(13) . . ?
O1C0 C1C O1C 36.1(15) . . ?
O2C C1C O1C 127.7(2) . . ?
O1C0 C1C C2C 116.8(10) . . ?
O2C C1C C2C 118.7(2) . . ?
O1C C1C C2C 113.6(2) . . ?
F2C C2C F3C 108.4(2) . . ?
F2C C2C F1C 107.8(2) . . ?
F3C C2C F1C 107.0(2) . . ?
F2C C2C C1C 111.6(2) . . ?
F3C C2C C1C 112.7(2) . . ?
F1C C2C C1C 109.1(2) . . ?
O1C0 O1C C1C 54.9(16) . . ?
O1C0 O1C H1C 85(3) . . ?
C1C O1C H1C 112(3) . . ?
O1C O1C0 C1C 89(2) . . ?
O1C O1C0 H1C 55(3) . . ?
C1C O1C0 H1C 114(3) . . ?
C1C O2C H1F 139(2) . . ?
O2D C1D O1D 128.9(2) . . ?
O2D C1D C2D 121.0(2) . . ?
O1D C1D C2D 110.1(2) . . ?
F3D C2D F1D 108.2(2) . . ?
F3D C2D F2D 107.9(2) . . ?
F1D C2D F2D 107.1(2) . . ?
F3D C2D C1D 111.7(2) . . ?
F1D C2D C1D 112.2(2) . . ?
F2D C2D C1D 109.5(2) . . ?
C1D O1D H1D 105(2) . . ?
O2F C1F O1F 128.4(3) . . ?
O2F C1F C2F 120.8(3) . . ?
O1F C1F C2F 110.7(3) . . ?
F1F C2F F3F 110.0(4) . . ?
F1F C2F F2F 107.0(3) . . ?
F3F C2F F2F 105.3(4) . . ?
F1F C2F C1F 113.7(3) . . ?
F3F C2F C1F 109.4(3) . . ?
F2F C2F C1F 111.1(3) . . ?
C1F O1F H1F 125(3) . . ?
Cl1 C57 Cl2 111.2(9) . . ?
Cl1 C57 H57A 109.4 . . ?
Cl2 C57 H57A 109.4 . . ?
Cl1 C57 H57B 109.4 . . ?
Cl2 C57 H57B 109.4 . . ?
H57A C57 H57B 108.0 . . ?
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
N21 C4 1.368(3) . ?
N21 C1 1.371(3) . ?
N21 H21 0.86(3) . ?
N22 C6 1.371(3) . ?
N22 C9 1.375(3) . ?
N22 H22 0.91(3) . ?
N23 C14 1.373(3) . ?
N23 C11 1.375(3) . ?
N23 H23 0.90(3) . ?
N24 C19 1.370(3) . ?
N24 C16 1.373(3) . ?
N24 H24 0.87(3) . ?
C1 C20 1.406(3) . ?
C1 C2 1.422(3) . ?
C2 C3 1.357(3) . ?
C2 H2 0.88(2) . ?
C3 C4 1.422(3) . ?
C3 H3 0.95(3) . ?
C4 C5 1.411(3) . ?
C5 C6 1.415(3) . ?
C5 C25 1.423(3) . ?
C6 C7 1.427(3) . ?
C7 C8 1.360(3) . ?
C7 H7 0.93(2) . ?
C8 C9 1.426(3) . ?
C8 H8 0.96(3) . ?
C9 C10 1.410(3) . ?
C10 C11 1.410(3) . ?
C10 C33 1.421(3) . ?
C11 C12 1.426(3) . ?
C12 C13 1.363(3) . ?
C12 H12 0.93(3) . ?
C13 C14 1.429(3) . ?
C13 H13 0.88(3) . ?
C14 C15 1.409(3) . ?
C15 C16 1.411(3) . ?
C15 C41 1.427(3) . ?
C16 C17 1.421(3) . ?
C17 C18 1.356(3) . ?
C17 H17 0.99(3) . ?
C18 C19 1.423(3) . ?
C18 H18 0.91(2) . ?
C19 C20 1.417(3) . ?
C20 C49 1.419(3) . ?
C25 C26 1.197(3) . ?
C26 C27 1.435(3) . ?
C27 C28 1.395(4) . ?
C27 C32 1.395(3) . ?
C28 C29 1.380(4) . ?
C28 H28 0.99(3) . ?
C29 C30 1.362(5) . ?
C29 H29 0.98(4) . ?
C30 C31 1.362(5) . ?
C30 H30 1.05(4) . ?
C31 C32 1.388(4) . ?
C31 H31 0.93(4) . ?
C32 H32 0.93(3) . ?
C33 C34 1.199(3) . ?
C34 C35 1.437(3) . ?
C35 C40 1.391(3) . ?
C35 C36 1.394(3) . ?
C36 C37 1.379(3) . ?
C36 H36 0.96(3) . ?
C37 C38 1.383(4) . ?
C37 H37 0.92(3) . ?
C38 C39 1.376(4) . ?
C38 H38 1.01(3) . ?
C39 C40 1.389(3) . ?
C39 H39 0.98(3) . ?
C40 H40 0.93(3) . ?
C41 C42 1.197(3) . ?
C42 C43 1.435(3) . ?
C43 C44 1.396(3) . ?
C43 C48 1.401(3) . ?
C44 C45 1.379(3) . ?
C44 H44 0.98(3) . ?
C45 C46 1.387(3) . ?
C45 H45 0.98(2) . ?
C46 C47 1.382(3) . ?
C46 H46 0.98(2) . ?
C47 C48 1.380(3) . ?
C47 H47 1.01(3) . ?
C48 H48 0.98(3) . ?
C49 C50 1.198(3) . ?
C50 C51 1.431(3) . ?
C51 C52 1.394(3) . ?
C51 C56 1.395(3) . ?
C52 C53 1.379(3) . ?
C52 H52 0.91(3) . ?
C53 C54 1.376(4) . ?
C53 H53 0.97(3) . ?
C54 C55 1.382(4) . ?
C54 H54 1.01(3) . ?
C55 C56 1.392(3) . ?
C55 H55 0.98(3) . ?
C56 H56 0.90(3) . ?
C1A O2A 1.236(3) . ?
C1A O1A 1.248(2) . ?
C1A C2A 1.537(3) . ?
C2A F3A 1.328(3) . ?
C2A F2A 1.329(2) . ?
C2A F1A 1.337(3) . ?
C1B O1B 1.241(3) . ?
C1B O2B0 1.250(15) . ?
C1B O2B 1.259(3) . ?
C1B C2B 1.537(3) . ?
C2B F1B 1.318(3) . ?
C2B F2B 1.330(3) . ?
C2B F3B 1.342(3) . ?
O2B O2B0 0.74(2) . ?
C1C O1C0 1.06(2) . ?
C1C O2C 1.205(3) . ?
C1C O1C 1.296(4) . ?
C1C C2C 1.531(3) . ?
C2C F2C 1.322(3) . ?
C2C F3C 1.330(3) . ?
C2C F1C 1.342(3) . ?
O1C O1C0 0.76(3) . ?
O1C H1C 0.99(5) . ?
O1C0 H1C 1.20(5) . ?
O2C H1F 1.45(7) . ?
C1D O2D 1.202(3) . ?
C1D O1D 1.298(3) . ?
C1D C2D 1.534(3) . ?
C2D F3D 1.320(3) . ?
C2D F1D 1.328(3) . ?
C2D F2D 1.342(3) . ?
O1D H1D 0.86(4) . ?
C1F O2F 1.213(4) . ?
C1F O1F 1.294(4) . ?
C1F C2F 1.527(5) . ?
C2F F1F 1.282(4) . ?
C2F F3F 1.317(5) . ?
C2F F2F 1.322(5) . ?
O1F H1F 1.14(7) . ?
Cl1 C57 1.728(16) . ?
Cl2 C57 1.749(16) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
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
N21 H21 O1B 0.86(3) 1.93(3) 2.785(2) 175(2) .
N22 H22 O1A 0.91(3) 1.90(3) 2.803(3) 177(2) .
N22 H22 O2A 0.91(3) 2.64(3) 3.212(3) 122(2) .
N23 H23 O1B 0.90(3) 1.90(3) 2.796(2) 174(2) .
N24 H24 O1A 0.87(3) 1.95(3) 2.817(2) 175(3) .
O1C H1C O2B 0.99(5) 1.49(5) 2.463(3) 167(4) .
O1D H1D O2A 0.86(4) 1.72(4) 2.539(2) 157(4) .
O1F H1F O2C 1.14(7) 1.45(7) 2.576(3) 167(5) .
C29 H29 Cl2 0.98(4) 2.46(4) 3.017(6) 116(3) 1_455
C44 H44 F1A 0.98(3) 2.50(3) 3.195(3) 127.8(19) 1_655
C47 H47 F2D 1.01(3) 2.62(3) 3.463(3) 140.6(19) 2_666
C48 H48 O2D 0.98(3) 2.52(3) 3.364(3) 144(2) 2_666
C36 H36 Cl1 0.96(3) 2.98(3) 3.918(4) 165.7(19) 2_777
C52 H52 F2D 0.91(3) 2.55(3) 3.312(3) 142(2) 1_545
C54 H54 O2A 1.01(3) 2.53(3) 3.511(3) 164(2) 1_445
