#------------------------------------------------------------------------------
#$Date: 2017-02-17 08:57:54 +0200 (Fri, 17 Feb 2017) $
#$Revision: 192220 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119169.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_7119169
loop_
_publ_author_name
'Yohei Haketa'
'Ryota Takasago'
'Hiromitsu Maeda'
_publ_section_title
;
 beta-Perfluoroalkyl-substituted pyrrole as an anion-responsive
 pi-electronic system through a single NH moiety
;
_journal_name_full               Chem.Commun.
_journal_page_first              7364
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C21 H11 F26 N O2'
_chemical_formula_sum            'C21 H11 F26 N O2'
_chemical_formula_weight         800.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_update_record
;
2016-04-25 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                98.783(18)
_cell_angle_beta                 91.487(6)
_cell_angle_gamma                104.872(7)
_cell_formula_units_Z            4
_cell_length_a                   12.370(3)
_cell_length_b                   12.834(4)
_cell_length_c                   18.490(5)
_cell_measurement_reflns_used    3129
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      25.3
_cell_volume                     2797.3(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35192
_diffrn_reflns_theta_full        65.99
_diffrn_reflns_theta_max         65.99
_diffrn_reflns_theta_min         6.52
_exptl_absorpt_coefficient_mu    2.234
_exptl_absorpt_correction_T_max  0.8965
_exptl_absorpt_correction_T_min  0.4073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.907
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prims
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.450
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     901
_refine_ls_number_reflns         9502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0950P)²+1.6855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                8308
_reflns_number_total             9502
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc03619h2.cif
_cod_data_source_block           50622m
_cod_original_cell_volume        2797.3(13)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7119169
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
F1 F 0.53000(12) 0.92554(11) 0.11831(7) 0.0262(3) Uani 1 1 d . . .
F2 F 0.48102(11) 0.79492(12) 0.02348(7) 0.0272(3) Uani 1 1 d . . .
F3 F 0.75185(11) 0.90992(12) 0.10568(7) 0.0276(3) Uani 1 1 d . . .
F4 F 0.69272(12) 0.79401(11) 0.00444(7) 0.0269(3) Uani 1 1 d . . .
F5 F 0.68622(14) 1.06584(12) 0.05446(8) 0.0351(4) Uani 1 1 d . . .
F6 F 0.59158(12) 0.95375(12) -0.03957(8) 0.0314(3) Uani 1 1 d . . .
F7 F 0.87589(14) 0.99151(17) -0.00043(11) 0.0526(5) Uani 1 1 d . . .
F8 F 0.76766(15) 0.91867(14) -0.09886(9) 0.0457(4) Uani 1 1 d . . .
F9 F 0.86008(18) 1.18668(16) -0.00909(12) 0.0623(6) Uani 1 1 d . . .
F10 F 0.71739(14) 1.12973(15) -0.08774(10) 0.0447(4) Uani 1 1 d . . .
F11 F 0.98321(16) 1.0943(2) -0.11295(13) 0.0658(6) Uani 1 1 d . . .
F12 F 0.8437(2) 1.0586(2) -0.19020(12) 0.0778(7) Uani 1 1 d . . .
F13 F 0.9134(2) 1.2230(2) -0.14019(16) 0.0849(8) Uani 1 1 d . . .
F14 F 0.64478(12) 0.84120(12) 0.32501(7) 0.0299(3) Uani 1 1 d . . .
F15 F 0.64560(11) 0.95003(11) 0.24554(7) 0.0258(3) Uani 1 1 d . . .
F16 F 0.43270(13) 0.79423(11) 0.33345(8) 0.0320(3) Uani 1 1 d . . .
F17 F 0.40042(11) 0.85191(12) 0.23243(7) 0.0290(3) Uani 1 1 d . . .
F18 F 0.56649(12) 1.01788(12) 0.38231(8) 0.0327(4) Uani 1 1 d . . .
F19 F 0.48502(13) 1.05449(12) 0.28705(8) 0.0329(4) Uani 1 1 d . . .
F20 F 0.38197(14) 0.94908(14) 0.44116(8) 0.0377(4) Uani 1 1 d . . .
F21 F 0.27943(12) 0.92189(13) 0.33950(9) 0.0361(4) Uani 1 1 d . . .
F22 F 0.45015(14) 1.17647(13) 0.41754(11) 0.0484(5) Uani 1 1 d . A 1
F23 F 0.30864(15) 1.12736(14) 0.33709(9) 0.0418(4) Uani 1 1 d . A 1
F24 F 0.31845(19) 1.1140(2) 0.52274(9) 0.0644(6) Uani 1 1 d . . .
F25 F 0.17890(14) 1.03515(15) 0.44534(10) 0.0473(5) Uani 1 1 d . . .
F26 F 0.24636(16) 1.20934(15) 0.46104(11) 0.0522(5) Uani 1 1 d . . .
F27 F 0.86159(11) 0.27337(11) 0.25861(7) 0.0246(3) Uani 1 1 d . . .
F28 F 0.85628(12) 0.12952(12) 0.17735(7) 0.0300(3) Uani 1 1 d . . .
F29 F 1.10429(11) 0.29442(12) 0.27054(8) 0.0294(3) Uani 1 1 d . . .
F30 F 1.06908(13) 0.17572(12) 0.16977(8) 0.0328(4) Uani 1 1 d . . .
F31 F 1.02951(13) 0.43610(12) 0.21598(8) 0.0335(4) Uani 1 1 d . . .
F32 F 0.93648(12) 0.31817(13) 0.12362(8) 0.0316(3) Uani 1 1 d . . .
F33 F 1.22505(12) 0.37503(14) 0.15811(9) 0.0369(4) Uani 1 1 d . . .
F34 F 1.11553(13) 0.29896(13) 0.06028(8) 0.0360(4) Uani 1 1 d . . .
F35 F 1.20087(17) 0.56606(14) 0.15188(10) 0.0503(5) Uani 1 1 d . . .
F36 F 1.04936(14) 0.50551(15) 0.07909(10) 0.0450(4) Uani 1 1 d . . .
F37 F 1.24723(18) 0.60818(17) 0.02203(13) 0.0629(6) Uani 1 1 d . . .
F38 F 1.16395(16) 0.44570(18) -0.03172(9) 0.0553(5) Uani 1 1 d . . .
F39 F 1.31255(13) 0.47329(16) 0.03866(10) 0.0485(5) Uani 1 1 d . . .
F40 F 1.01993(11) 0.28774(11) 0.47979(7) 0.0243(3) Uani 1 1 d . . .
F41 F 0.97690(11) 0.35593(10) 0.38522(7) 0.0230(3) Uani 1 1 d . . .
F42 F 0.80880(11) 0.20111(11) 0.50027(7) 0.0258(3) Uani 1 1 d . . .
F43 F 0.75094(11) 0.23586(12) 0.39628(7) 0.0280(3) Uani 1 1 d . . .
F44 F 0.91400(11) 0.43329(11) 0.53461(8) 0.0269(3) Uani 1 1 d . . .
F45 F 0.81349(13) 0.44578(12) 0.43941(8) 0.0325(4) Uani 1 1 d . . .
F46 F 0.74324(13) 0.34959(13) 0.60229(8) 0.0337(4) Uani 1 1 d . . .
F47 F 0.62948(12) 0.30437(13) 0.50459(9) 0.0385(4) Uani 1 1 d . . .
F48 F 0.78282(14) 0.57105(13) 0.57385(11) 0.0467(5) Uani 1 1 d . . .
F49 F 0.63682(15) 0.50662(16) 0.49630(11) 0.0506(5) Uani 1 1 d . . .
F50 F 0.66214(18) 0.4995(2) 0.68315(11) 0.0648(6) Uani 1 1 d . . .
F51 F 0.52011(14) 0.41732(16) 0.60845(11) 0.0520(5) Uani 1 1 d . . .
F52 F 0.58274(19) 0.59187(18) 0.62208(15) 0.0747(7) Uani 1 1 d . . .
C1 C 0.54373(19) 0.6458(2) 0.09755(12) 0.0213(5) Uani 1 1 d . . .
H1 H 0.5314 0.6167 0.0467 0.026 Uiso 1 1 calc R . .
C2 C 0.55689(19) 0.75229(19) 0.12789(13) 0.0209(5) Uani 1 1 d . . .
C3 C 0.57436(19) 0.75969(19) 0.20592(12) 0.0210(5) Uani 1 1 d . . .
C4 C 0.56961(19) 0.65828(19) 0.21944(12) 0.0222(5) Uani 1 1 d . . .
H2 H 0.5774 0.6387 0.2664 0.027 Uiso 1 1 calc R . .
C5 C 0.55740(19) 0.8375(2) 0.08169(12) 0.0219(5) Uani 1 1 d . . .
C6 C 0.67255(19) 0.87871(19) 0.04972(12) 0.0216(5) Uani 1 1 d . . .
C7 C 0.6827(2) 0.97462(19) 0.00679(13) 0.0226(5) Uani 1 1 d . . .
C8 C 0.7873(2) 0.9984(2) -0.03859(14) 0.0280(6) Uani 1 1 d . . .
C9 C 0.8109(3) 1.1081(3) -0.06670(19) 0.0435(7) Uani 1 1 d . . .
C10 C 0.8925(3) 1.1235(3) -0.12653(19) 0.0481(8) Uani 1 1 d . . .
C11 C 0.5872(2) 0.85578(19) 0.26559(12) 0.0217(5) Uani 1 1 d . . .
C12 C 0.4726(2) 0.86996(19) 0.29131(13) 0.0225(5) Uani 1 1 d . . .
C13 C 0.4762(2) 0.98426(19) 0.33512(13) 0.0228(5) Uani 1 1 d . . .
C14 C 0.3711(2) 0.9877(2) 0.37857(13) 0.0250(5) Uani 1 1 d . . .
C15 C 0.3521(2) 1.1029(2) 0.39737(14) 0.0296(6) Uani 1 1 d . A 1
C16 C 0.2714(2) 1.1153(2) 0.45869(15) 0.0356(6) Uani 1 1 d . . .
C17 C 0.54642(19) 0.47511(19) 0.14042(13) 0.0217(5) Uani 1 1 d . . .
C18 C 0.5739(2) 0.32809(19) 0.20210(13) 0.0239(5) Uani 1 1 d . . .
C19 C 0.4553(2) 0.2569(2) 0.18670(16) 0.0366(6) Uani 1 1 d . . .
H3 H 0.4294 0.2566 0.1361 0.055 Uiso 1 1 calc R . .
H4 H 0.4062 0.2857 0.2206 0.055 Uiso 1 1 calc R . .
H5 H 0.4531 0.1821 0.1935 0.055 Uiso 1 1 calc R . .
C20 C 0.6541(2) 0.2966(2) 0.14759(14) 0.0338(6) Uani 1 1 d . . .
H6 H 0.7293 0.3456 0.1604 0.051 Uiso 1 1 calc R . .
H7 H 0.6285 0.3026 0.0982 0.051 Uiso 1 1 calc R . .
H8 H 0.6562 0.2211 0.1489 0.051 Uiso 1 1 calc R . .
C21 C 0.6187(2) 0.3320(2) 0.27986(13) 0.0263(5) Uani 1 1 d . . .
H9 H 0.6955 0.3792 0.2877 0.039 Uiso 1 1 calc R . .
H10 H 0.6185 0.2581 0.2875 0.039 Uiso 1 1 calc R . .
H11 H 0.5710 0.3613 0.3146 0.039 Uiso 1 1 calc R . .
C22 C 0.91905(19) 0.02162(19) 0.28179(13) 0.0223(5) Uani 1 1 d . . .
H12 H 0.9077 -0.0227 0.2347 0.027 Uiso 1 1 calc R . .
C23 C 0.92313(19) 0.12970(19) 0.29604(13) 0.0210(5) Uani 1 1 d . . .
C24 C 0.94229(19) 0.16334(19) 0.37445(13) 0.0210(5) Uani 1 1 d . . .
C25 C 0.9486(2) 0.07527(19) 0.40385(13) 0.0222(5) Uani 1 1 d . . .
H13 H 0.9609 0.0736 0.4545 0.027 Uiso 1 1 calc R . .
C26 C 0.9156(2) 0.19519(19) 0.23750(12) 0.0223(5) Uani 1 1 d . . .
C27 C 1.0310(2) 0.2523(2) 0.21161(13) 0.0237(5) Uani 1 1 d . . .
C28 C 1.0300(2) 0.3459(2) 0.16804(13) 0.0245(5) Uani 1 1 d . . .
C29 C 1.1314(2) 0.3759(2) 0.12014(14) 0.0270(5) Uani 1 1 d . . .
C30 C 1.1490(2) 0.4887(2) 0.09630(15) 0.0342(6) Uani 1 1 d . . .
C31 C 1.2201(2) 0.5040(3) 0.02927(17) 0.0413(7) Uani 1 1 d . . .
C32 C 0.94543(19) 0.26990(19) 0.42112(12) 0.0201(5) Uani 1 1 d . . .
C33 C 0.83012(19) 0.27129(19) 0.45202(12) 0.0213(5) Uani 1 1 d . . .
C34 C 0.82111(19) 0.38433(19) 0.49099(13) 0.0219(5) Uani 1 1 d . . .
C35 C 0.71936(19) 0.3800(2) 0.53880(14) 0.0252(5) Uani 1 1 d . . .
C36 C 0.6893(2) 0.4900(2) 0.55591(17) 0.0358(7) Uani 1 1 d . . .
C37 C 0.6119(3) 0.4989(3) 0.61956(19) 0.0452(8) Uani 1 1 d . . .
C38 C 0.9341(2) -0.11773(19) 0.36072(13) 0.0238(5) Uani 1 1 d . . .
C39 C 0.9034(2) -0.30646(19) 0.29952(14) 0.0264(5) Uani 1 1 d . . .
C40 C 0.8641(2) -0.3582(2) 0.22070(14) 0.0302(6) Uani 1 1 d . . .
H14 H 0.7892 -0.3499 0.2097 0.045 Uiso 1 1 calc R . .
H15 H 0.8615 -0.4360 0.2138 0.045 Uiso 1 1 calc R . .
H16 H 0.9164 -0.3220 0.1876 0.045 Uiso 1 1 calc R . .
C41 C 1.0182(2) -0.3171(2) 0.31981(16) 0.0386(7) Uani 1 1 d . . .
H17 H 1.0403 -0.2831 0.3710 0.058 Uiso 1 1 calc R . .
H18 H 1.0723 -0.2804 0.2879 0.058 Uiso 1 1 calc R . .
H19 H 1.0169 -0.3946 0.3138 0.058 Uiso 1 1 calc R . .
C42 C 0.8164(2) -0.3492(2) 0.35193(15) 0.0342(6) Uani 1 1 d . . .
H20 H 0.7436 -0.3403 0.3359 0.051 Uiso 1 1 calc R . .
H21 H 0.8392 -0.3081 0.4015 0.051 Uiso 1 1 calc R . .
H22 H 0.8102 -0.4268 0.3522 0.051 Uiso 1 1 calc R . .
O1 O 0.52221(15) 0.42192(14) 0.08018(9) 0.0275(4) Uani 1 1 d . . .
O2 O 0.57261(14) 0.44485(13) 0.20199(8) 0.0222(4) Uani 1 1 d . . .
N1 N 0.55140(16) 0.58776(16) 0.15323(10) 0.0214(4) Uani 1 1 d . . .
O3 O 0.95315(16) -0.13427(14) 0.42099(9) 0.0301(4) Uani 1 1 d . . .
O4 O 0.91089(14) -0.18810(13) 0.29826(9) 0.0239(4) Uani 1 1 d . . .
N2 N 0.93419(17) -0.01234(16) 0.34751(10) 0.0223(4) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 C1 N1 108.2(2) . .
C2 C1 H1 125.9 . .
N1 C1 H1 125.9 . .
C1 C2 C3 107.1(2) . .
C1 C2 C5 121.4(2) . .
C3 C2 C5 131.4(2) . .
C4 C3 C2 107.5(2) . .
C4 C3 C11 122.8(2) . .
C2 C3 C11 129.6(2) . .
C3 C4 N1 108.3(2) . .
C3 C4 H2 125.8 . .
N1 C4 H2 125.8 . .
F1 C5 F2 107.40(19) . .
F1 C5 C2 112.71(19) . .
F2 C5 C2 109.35(19) . .
F1 C5 C6 107.62(19) . .
F2 C5 C6 106.71(18) . .
C2 C5 C6 112.74(19) . .
F3 C6 F4 108.35(19) . .
F3 C6 C7 108.42(19) . .
F4 C6 C7 108.27(18) . .
F3 C6 C5 108.04(18) . .
F4 C6 C5 107.89(18) . .
C7 C6 C5 115.7(2) . .
F6 C7 F5 108.10(19) . .
F6 C7 C6 109.21(19) . .
F5 C7 C6 108.82(19) . .
F6 C7 C8 107.75(19) . .
F5 C7 C8 107.82(19) . .
C6 C7 C8 114.9(2) . .
F7 C8 F8 107.8(2) . .
F7 C8 C9 110.6(2) . .
F8 C8 C9 106.8(2) . .
F7 C8 C7 110.0(2) . .
F8 C8 C7 107.0(2) . .
C9 C8 C7 114.3(2) . .
F10 C9 F9 107.2(3) . .
F10 C9 C10 109.2(3) . .
F9 C9 C10 104.9(3) . .
F10 C9 C8 111.6(2) . .
F9 C9 C8 106.7(3) . .
C10 C9 C8 116.6(3) . .
F13 C10 F11 112.7(3) . .
F13 C10 F12 105.3(3) . .
F11 C10 F12 105.6(3) . .
F13 C10 C9 110.4(3) . .
F11 C10 C9 113.1(3) . .
F12 C10 C9 109.4(3) . .
F15 C11 F14 106.92(18) . .
F15 C11 C3 112.30(19) . .
F14 C11 C3 109.49(19) . .
F15 C11 C12 108.73(19) . .
F14 C11 C12 106.76(18) . .
C3 C11 C12 112.35(19) . .
F16 C12 F17 108.25(19) . .
F16 C12 C11 108.1(2) . .
F17 C12 C11 109.08(18) . .
F16 C12 C13 108.60(18) . .
F17 C12 C13 107.6(2) . .
C11 C12 C13 115.07(19) . .
F18 C13 F19 108.60(19) . .
F18 C13 C14 108.37(19) . .
F19 C13 C14 108.23(19) . .
F18 C13 C12 109.4(2) . .
F19 C13 C12 107.88(19) . .
C14 C13 C12 114.19(19) . .
F21 C14 F20 107.9(2) . .
F21 C14 C15 107.9(2) . .
F20 C14 C15 108.9(2) . .
F21 C14 C13 109.50(19) . .
F20 C14 C13 108.3(2) . .
C15 C14 C13 114.1(2) . .
F22 C15 F23 108.1(2) . .
F22 C15 C14 109.6(2) . .
F23 C15 C14 108.6(2) . .
F22 C15 C16 108.2(2) . .
F23 C15 C16 107.3(2) . .
C14 C15 C16 114.9(2) . .
F24 C16 F26 108.3(2) . .
F24 C16 F25 109.2(3) . .
F26 C16 F25 109.3(2) . .
F24 C16 C15 110.8(2) . .
F26 C16 C15 109.3(2) . .
F25 C16 C15 109.9(2) . .
O1 C17 O2 129.4(2) . .
O1 C17 N1 121.0(2) . .
O2 C17 N1 109.69(19) . .
O2 C18 C19 108.5(2) . .
O2 C18 C20 109.8(2) . .
C19 C18 C20 113.4(2) . .
O2 C18 C21 102.09(18) . .
C19 C18 C21 112.0(2) . .
C20 C18 C21 110.4(2) . .
C18 C19 H3 109.5 . .
C18 C19 H4 109.5 . .
H3 C19 H4 109.5 . .
C18 C19 H5 109.5 . .
H3 C19 H5 109.5 . .
H4 C19 H5 109.5 . .
C18 C20 H6 109.5 . .
C18 C20 H7 109.5 . .
H6 C20 H7 109.5 . .
C18 C20 H8 109.5 . .
H6 C20 H8 109.5 . .
H7 C20 H8 109.5 . .
C18 C21 H9 109.5 . .
C18 C21 H10 109.5 . .
H9 C21 H10 109.5 . .
C18 C21 H11 109.5 . .
H9 C21 H11 109.5 . .
H10 C21 H11 109.5 . .
C23 C22 N2 108.0(2) . .
C23 C22 H12 126.0 . .
N2 C22 H12 126.0 . .
C22 C23 C24 107.0(2) . .
C22 C23 C26 122.9(2) . .
C24 C23 C26 129.9(2) . .
C25 C24 C23 107.6(2) . .
C25 C24 C32 121.8(2) . .
C23 C24 C32 130.4(2) . .
C24 C25 N2 108.2(2) . .
C24 C25 H13 125.9 . .
N2 C25 H13 125.9 . .
F28 C26 F27 106.90(19) . .
F28 C26 C23 109.81(19) . .
F27 C26 C23 111.82(18) . .
F28 C26 C27 106.32(18) . .
F27 C26 C27 107.66(19) . .
C23 C26 C27 113.9(2) . .
F30 C27 F29 107.64(19) . .
F30 C27 C28 109.07(19) . .
F29 C27 C28 107.64(19) . .
F30 C27 C26 107.91(19) . .
F29 C27 C26 109.20(19) . .
C28 C27 C26 115.1(2) . .
F32 C28 F31 108.4(2) . .
F32 C28 C27 109.4(2) . .
F31 C28 C27 108.50(19) . .
F32 C28 C29 107.7(2) . .
F31 C28 C29 107.9(2) . .
C27 C28 C29 114.9(2) . .
F34 C29 F33 108.1(2) . .
F34 C29 C30 109.0(2) . .
F33 C29 C30 108.3(2) . .
F34 C29 C28 108.3(2) . .
F33 C29 C28 108.9(2) . .
C30 C29 C28 114.0(2) . .
F35 C30 F36 108.7(2) . .
F35 C30 C29 109.0(2) . .
F36 C30 C29 109.8(2) . .
F35 C30 C31 107.4(2) . .
F36 C30 C31 107.3(2) . .
C29 C30 C31 114.5(2) . .
F39 C31 F37 109.0(2) . .
F39 C31 F38 108.7(3) . .
F37 C31 F38 108.6(3) . .
F39 C31 C30 110.1(2) . .
F37 C31 C30 109.3(3) . .
F38 C31 C30 111.2(2) . .
F41 C32 F40 107.35(17) . .
F41 C32 C24 113.04(18) . .
F40 C32 C24 109.64(19) . .
F41 C32 C33 107.66(19) . .
F40 C32 C33 106.75(18) . .
C24 C32 C33 112.10(18) . .
F43 C33 F42 108.47(18) . .
F43 C33 C34 108.12(19) . .
F42 C33 C34 108.23(18) . .
F43 C33 C32 108.35(18) . .
F42 C33 C32 108.23(19) . .
C34 C33 C32 115.26(19) . .
F44 C34 F45 108.63(18) . .
F44 C34 C33 109.35(19) . .
F45 C34 C33 108.15(19) . .
F44 C34 C35 107.57(18) . .
F45 C34 C35 108.45(19) . .
C33 C34 C35 114.55(19) . .
F46 C35 F47 108.0(2) . .
F46 C35 C36 108.6(2) . .
F47 C35 C36 108.6(2) . .
F46 C35 C34 108.5(2) . .
F47 C35 C34 109.52(19) . .
C36 C35 C34 113.4(2) . .
F48 C36 F49 109.0(2) . .
F48 C36 C35 109.8(2) . .
F49 C36 C35 109.0(2) . .
F48 C36 C37 106.8(2) . .
F49 C36 C37 107.0(2) . .
C35 C36 C37 115.0(2) . .
F50 C37 F51 108.9(3) . .
F50 C37 F52 108.5(3) . .
F51 C37 F52 108.5(3) . .
F50 C37 C36 112.0(3) . .
F51 C37 C36 110.8(3) . .
F52 C37 C36 108.1(3) . .
O3 C38 O4 128.7(2) . .
O3 C38 N2 121.4(2) . .
O4 C38 N2 109.9(2) . .
O4 C39 C41 108.6(2) . .
O4 C39 C40 102.0(2) . .
C41 C39 C40 112.0(2) . .
O4 C39 C42 109.3(2) . .
C41 C39 C42 113.2(2) . .
C40 C39 C42 111.1(2) . .
C39 C40 H14 109.5 . .
C39 C40 H15 109.5 . .
H14 C40 H15 109.5 . .
C39 C40 H16 109.5 . .
H14 C40 H16 109.5 . .
H15 C40 H16 109.5 . .
C39 C41 H17 109.5 . .
C39 C41 H18 109.5 . .
H17 C41 H18 109.5 . .
C39 C41 H19 109.5 . .
H17 C41 H19 109.5 . .
H18 C41 H19 109.5 . .
C39 C42 H20 109.5 . .
C39 C42 H21 109.5 . .
H20 C42 H21 109.5 . .
C39 C42 H22 109.5 . .
H20 C42 H22 109.5 . .
H21 C42 H22 109.5 . .
C17 O2 C18 119.56(17) . .
C1 N1 C4 108.9(2) . .
C1 N1 C17 122.81(19) . .
C4 N1 C17 128.2(2) . .
C38 O4 C39 119.14(19) . .
C22 N2 C25 109.2(2) . .
C22 N2 C38 128.83(19) . .
C25 N2 C38 122.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.351(3) .
F2 C5 1.361(3) .
F3 C6 1.346(3) .
F4 C6 1.348(3) .
F5 C7 1.344(3) .
F6 C7 1.342(3) .
F7 C8 1.317(3) .
F8 C8 1.363(3) .
F9 C9 1.358(4) .
F10 C9 1.320(4) .
F11 C10 1.301(4) .
F12 C10 1.360(4) .
F13 C10 1.301(4) .
F14 C11 1.356(3) .
F15 C11 1.351(3) .
F16 C12 1.342(3) .
F17 C12 1.343(3) .
F18 C13 1.335(3) .
F19 C13 1.347(3) .
F20 C14 1.343(3) .
F21 C14 1.342(3) .
F22 C15 1.336(3) .
F23 C15 1.338(3) .
F24 C16 1.310(4) .
F25 C16 1.316(3) .
F26 C16 1.315(3) .
F27 C26 1.358(3) .
F28 C26 1.357(3) .
F29 C27 1.349(3) .
F30 C27 1.346(3) .
F31 C28 1.348(3) .
F32 C28 1.338(3) .
F33 C29 1.343(3) .
F34 C29 1.339(3) .
F35 C30 1.334(3) .
F36 C30 1.343(3) .
F37 C31 1.321(4) .
F38 C31 1.322(4) .
F39 C31 1.317(4) .
F40 C32 1.357(3) .
F41 C32 1.352(3) .
F42 C33 1.346(3) .
F43 C33 1.343(3) .
F44 C34 1.339(3) .
F45 C34 1.343(3) .
F46 C35 1.341(3) .
F47 C35 1.342(3) .
F48 C36 1.337(3) .
F49 C36 1.337(4) .
F50 C37 1.314(4) .
F51 C37 1.319(4) .
F52 C37 1.327(4) .
C1 C2 1.362(3) .
C1 N1 1.375(3) .
C1 H1 0.9500 .
C2 C3 1.438(3) .
C2 C5 1.486(4) .
C3 C4 1.349(4) .
C3 C11 1.496(3) .
C4 N1 1.382(3) .
C4 H2 0.9500 .
C5 C6 1.553(3) .
C6 C7 1.544(4) .
C7 C8 1.551(3) .
C8 C9 1.535(4) .
C9 C10 1.517(4) .
C11 C12 1.553(3) .
C12 C13 1.553(3) .
C13 C14 1.552(3) .
C14 C15 1.546(4) .
C15 C16 1.546(4) .
C17 O1 1.201(3) .
C17 O2 1.316(3) .
C17 N1 1.414(3) .
C18 O2 1.503(3) .
C18 C19 1.510(4) .
C18 C20 1.515(4) .
C18 C21 1.516(3) .
C19 H3 0.9800 .
C19 H4 0.9800 .
C19 H5 0.9800 .
C20 H6 0.9800 .
C20 H7 0.9800 .
C20 H8 0.9800 .
C21 H9 0.9800 .
C21 H10 0.9800 .
C21 H11 0.9800 .
C22 C23 1.359(3) .
C22 N2 1.376(3) .
C22 H12 0.9500 .
C23 C24 1.443(3) .
C23 C26 1.483(3) .
C24 C25 1.345(4) .
C24 C32 1.492(3) .
C25 N2 1.382(3) .
C25 H13 0.9500 .
C26 C27 1.552(3) .
C27 C28 1.547(4) .
C28 C29 1.555(3) .
C29 C30 1.542(4) .
C30 C31 1.546(4) .
C32 C33 1.554(3) .
C33 C34 1.551(3) .
C34 C35 1.551(3) .
C35 C36 1.540(4) .
C36 C37 1.546(4) .
C38 O3 1.194(3) .
C38 O4 1.328(3) .
C38 N2 1.411(3) .
C39 O4 1.502(3) .
C39 C41 1.505(4) .
C39 C40 1.517(3) .
C39 C42 1.520(4) .
C40 H14 0.9800 .
C40 H15 0.9800 .
C40 H16 0.9800 .
C41 H17 0.9800 .
C41 H18 0.9800 .
C41 H19 0.9800 .
C42 H20 0.9800 .
C42 H21 0.9800 .
C42 H22 0.9800 .
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
N1 C1 C2 C3 0.5(3) . . . .
N1 C1 C2 C5 177.6(2) . . . .
C1 C2 C3 C4 -0.8(3) . . . .
C5 C2 C3 C4 -177.5(2) . . . .
C1 C2 C3 C11 -176.4(2) . . . .
C5 C2 C3 C11 7.0(4) . . . .
C2 C3 C4 N1 0.8(3) . . . .
C11 C3 C4 N1 176.7(2) . . . .
C1 C2 C5 F1 157.1(2) . . . .
C3 C2 C5 F1 -26.7(3) . . . .
C1 C2 C5 F2 37.7(3) . . . .
C3 C2 C5 F2 -146.0(2) . . . .
C1 C2 C5 C6 -80.8(3) . . . .
C3 C2 C5 C6 95.4(3) . . . .
F1 C5 C6 F3 71.8(2) . . . .
F2 C5 C6 F3 -173.13(18) . . . .
C2 C5 C6 F3 -53.1(2) . . . .
F1 C5 C6 F4 -171.22(18) . . . .
F2 C5 C6 F4 -56.2(2) . . . .
C2 C5 C6 F4 63.9(2) . . . .
F1 C5 C6 C7 -49.8(2) . . . .
F2 C5 C6 C7 65.2(2) . . . .
C2 C5 C6 C7 -174.75(19) . . . .
F3 C6 C7 F6 -167.70(17) . . . .
F4 C6 C7 F6 74.9(2) . . . .
C5 C6 C7 F6 -46.2(3) . . . .
F3 C6 C7 F5 -49.9(2) . . . .
F4 C6 C7 F5 -167.25(18) . . . .
C5 C6 C7 F5 71.6(2) . . . .
F3 C6 C7 C8 71.1(2) . . . .
F4 C6 C7 C8 -46.3(3) . . . .
C5 C6 C7 C8 -167.42(19) . . . .
F6 C7 C8 F7 -163.8(2) . . . .
F5 C7 C8 F7 79.7(3) . . . .
C6 C7 C8 F7 -41.8(3) . . . .
F6 C7 C8 F8 -47.0(3) . . . .
F5 C7 C8 F8 -163.4(2) . . . .
C6 C7 C8 F8 75.0(3) . . . .
F6 C7 C8 C9 71.1(3) . . . .
F5 C7 C8 C9 -45.4(3) . . . .
C6 C7 C8 C9 -166.9(2) . . . .
F7 C8 C9 F10 -163.3(2) . . . .
F8 C8 C9 F10 79.7(3) . . . .
C7 C8 C9 F10 -38.5(3) . . . .
F7 C8 C9 F9 -46.5(3) . . . .
F8 C8 C9 F9 -163.6(2) . . . .
C7 C8 C9 F9 78.3(3) . . . .
F7 C8 C9 C10 70.2(3) . . . .
F8 C8 C9 C10 -46.8(3) . . . .
C7 C8 C9 C10 -165.0(3) . . . .
F10 C9 C10 F13 58.6(4) . . . .
F9 C9 C10 F13 -56.0(4) . . . .
C8 C9 C10 F13 -173.8(3) . . . .
F10 C9 C10 F11 -174.2(3) . . . .
F9 C9 C10 F11 71.2(4) . . . .
C8 C9 C10 F11 -46.5(4) . . . .
F10 C9 C10 F12 -56.8(4) . . . .
F9 C9 C10 F12 -171.4(3) . . . .
C8 C9 C10 F12 70.8(4) . . . .
C4 C3 C11 F15 147.9(2) . . . .
C2 C3 C11 F15 -37.1(3) . . . .
C4 C3 C11 F14 29.3(3) . . . .
C2 C3 C11 F14 -155.7(2) . . . .
C4 C3 C11 C12 -89.2(3) . . . .
C2 C3 C11 C12 85.8(3) . . . .
F15 C11 C12 F16 -159.19(17) . . . .
F14 C11 C12 F16 -44.2(2) . . . .
C3 C11 C12 F16 75.9(2) . . . .
F15 C11 C12 F17 83.3(2) . . . .
F14 C11 C12 F17 -161.65(18) . . . .
C3 C11 C12 F17 -41.6(3) . . . .
F15 C11 C12 C13 -37.7(3) . . . .
F14 C11 C12 C13 77.4(2) . . . .
C3 C11 C12 C13 -162.6(2) . . . .
F16 C12 C13 F18 79.2(2) . . . .
F17 C12 C13 F18 -163.81(18) . . . .
C11 C12 C13 F18 -42.0(3) . . . .
F16 C12 C13 F19 -162.78(18) . . . .
F17 C12 C13 F19 -45.8(2) . . . .
C11 C12 C13 F19 76.0(2) . . . .
F16 C12 C13 C14 -42.4(3) . . . .
F17 C12 C13 C14 74.5(2) . . . .
C11 C12 C13 C14 -163.7(2) . . . .
F18 C13 C14 F21 -159.2(2) . . . .
F19 C13 C14 F21 83.2(2) . . . .
C12 C13 C14 F21 -37.0(3) . . . .
F18 C13 C14 F20 -41.8(3) . . . .
F19 C13 C14 F20 -159.40(19) . . . .
C12 C13 C14 F20 80.4(2) . . . .
F18 C13 C14 C15 79.7(3) . . . .
F19 C13 C14 C15 -37.9(3) . . . .
C12 C13 C14 C15 -158.1(2) . . . .
F21 C14 C15 F22 -162.7(2) . . . .
F20 C14 C15 F22 80.4(3) . . . .
C13 C14 C15 F22 -40.8(3) . . . .
F21 C14 C15 F23 -44.8(3) . . . .
F20 C14 C15 F23 -161.72(19) . . . .
C13 C14 C15 F23 77.1(3) . . . .
F21 C14 C15 C16 75.3(3) . . . .
F20 C14 C15 C16 -41.6(3) . . . .
C13 C14 C15 C16 -162.8(2) . . . .
F22 C15 C16 F24 -51.1(3) . . . .
F23 C15 C16 F24 -167.5(2) . . . .
C14 C15 C16 F24 71.7(3) . . . .
F22 C15 C16 F26 68.2(3) . . . .
F23 C15 C16 F26 -48.3(3) . . . .
C14 C15 C16 F26 -169.1(2) . . . .
F22 C15 C16 F25 -171.8(2) . . . .
F23 C15 C16 F25 71.7(3) . . . .
C14 C15 C16 F25 -49.1(3) . . . .
N2 C22 C23 C24 0.3(3) . . . .
N2 C22 C23 C26 176.8(2) . . . .
C22 C23 C24 C25 -0.1(3) . . . .
C26 C23 C24 C25 -176.3(2) . . . .
C22 C23 C24 C32 -174.7(2) . . . .
C26 C23 C24 C32 9.1(4) . . . .
C23 C24 C25 N2 -0.1(3) . . . .
C32 C24 C25 N2 175.1(2) . . . .
C22 C23 C26 F28 27.6(3) . . . .
C24 C23 C26 F28 -156.7(2) . . . .
C22 C23 C26 F27 146.1(2) . . . .
C24 C23 C26 F27 -38.2(3) . . . .
C22 C23 C26 C27 -91.5(3) . . . .
C24 C23 C26 C27 84.2(3) . . . .
F28 C26 C27 F30 -46.4(2) . . . .
F27 C26 C27 F30 -160.70(18) . . . .
C23 C26 C27 F30 74.7(2) . . . .
F28 C26 C27 F29 -163.15(18) . . . .
F27 C26 C27 F29 82.6(2) . . . .
C23 C26 C27 F29 -42.1(3) . . . .
F28 C26 C27 C28 75.7(2) . . . .
F27 C26 C27 C28 -38.6(3) . . . .
C23 C26 C27 C28 -163.25(19) . . . .
F30 C27 C28 F32 82.6(2) . . . .
F29 C27 C28 F32 -160.90(18) . . . .
C26 C27 C28 F32 -38.9(3) . . . .
F30 C27 C28 F31 -159.33(19) . . . .
F29 C27 C28 F31 -42.8(2) . . . .
C26 C27 C28 F31 79.2(2) . . . .
F30 C27 C28 C29 -38.6(3) . . . .
F29 C27 C28 C29 78.0(2) . . . .
C26 C27 C28 C29 -160.0(2) . . . .
F32 C28 C29 F34 -46.0(3) . . . .
F31 C28 C29 F34 -162.8(2) . . . .
C27 C28 C29 F34 76.1(3) . . . .
F32 C28 C29 F33 -163.44(19) . . . .
F31 C28 C29 F33 79.8(3) . . . .
C27 C28 C29 F33 -41.4(3) . . . .
F32 C28 C29 C30 75.5(3) . . . .
F31 C28 C29 C30 -41.3(3) . . . .
C27 C28 C29 C30 -162.4(2) . . . .
F34 C29 C30 F35 -159.3(2) . . . .
F33 C29 C30 F35 -41.9(3) . . . .
C28 C29 C30 F35 79.5(3) . . . .
F34 C29 C30 F36 81.7(3) . . . .
F33 C29 C30 F36 -160.8(2) . . . .
C28 C29 C30 F36 -39.5(3) . . . .
F34 C29 C30 C31 -39.0(3) . . . .
F33 C29 C30 C31 78.4(3) . . . .
C28 C29 C30 C31 -160.2(2) . . . .
F35 C30 C31 F39 72.4(3) . . . .
F36 C30 C31 F39 -171.0(2) . . . .
C29 C30 C31 F39 -48.9(3) . . . .
F35 C30 C31 F37 -47.3(3) . . . .
F36 C30 C31 F37 69.4(3) . . . .
C29 C30 C31 F37 -168.5(2) . . . .
F35 C30 C31 F38 -167.2(2) . . . .
F36 C30 C31 F38 -50.5(3) . . . .
C29 C30 C31 F38 71.6(3) . . . .
C25 C24 C32 F41 158.4(2) . . . .
C23 C24 C32 F41 -27.7(3) . . . .
C25 C24 C32 F40 38.7(3) . . . .
C23 C24 C32 F40 -147.4(2) . . . .
C25 C24 C32 C33 -79.7(3) . . . .
C23 C24 C32 C33 94.2(3) . . . .
F41 C32 C33 F43 75.2(2) . . . .
F40 C32 C33 F43 -169.76(17) . . . .
C24 C32 C33 F43 -49.7(3) . . . .
F41 C32 C33 F42 -167.33(16) . . . .
F40 C32 C33 F42 -52.3(2) . . . .
C24 C32 C33 F42 67.7(2) . . . .
F41 C32 C33 C34 -46.0(3) . . . .
F40 C32 C33 C34 69.0(2) . . . .
C24 C32 C33 C34 -170.94(19) . . . .
F43 C33 C34 F44 -165.20(17) . . . .
F42 C33 C34 F44 77.5(2) . . . .
C32 C33 C34 F44 -43.8(3) . . . .
F43 C33 C34 F45 -47.1(2) . . . .
F42 C33 C34 F45 -164.38(17) . . . .
C32 C33 C34 F45 74.3(2) . . . .
F43 C33 C34 C35 74.0(2) . . . .
F42 C33 C34 C35 -43.3(3) . . . .
C32 C33 C34 C35 -164.6(2) . . . .
F44 C34 C35 F46 -43.6(2) . . . .
F45 C34 C35 F46 -160.93(18) . . . .
C33 C34 C35 F46 78.2(2) . . . .
F44 C34 C35 F47 -161.3(2) . . . .
F45 C34 C35 F47 81.4(2) . . . .
C33 C34 C35 F47 -39.5(3) . . . .
F44 C34 C35 C36 77.2(3) . . . .
F45 C34 C35 C36 -40.2(3) . . . .
C33 C34 C35 C36 -161.0(2) . . . .
F46 C35 C36 F48 77.3(3) . . . .
F47 C35 C36 F48 -165.5(2) . . . .
C34 C35 C36 F48 -43.4(3) . . . .
F46 C35 C36 F49 -163.35(19) . . . .
F47 C35 C36 F49 -46.1(3) . . . .
C34 C35 C36 F49 75.9(3) . . . .
F46 C35 C36 C37 -43.1(3) . . . .
F47 C35 C36 C37 74.1(3) . . . .
C34 C35 C36 C37 -163.9(2) . . . .
F48 C36 C37 F50 -54.2(3) . . . .
F49 C36 C37 F50 -170.9(3) . . . .
C35 C36 C37 F50 67.8(3) . . . .
F48 C36 C37 F51 -176.0(3) . . . .
F49 C36 C37 F51 67.4(3) . . . .
C35 C36 C37 F51 -53.9(4) . . . .
F48 C36 C37 F52 65.3(3) . . . .
F49 C36 C37 F52 -51.4(3) . . . .
C35 C36 C37 F52 -172.7(3) . . . .
O1 C17 O2 C18 -0.4(4) . . . .
N1 C17 O2 C18 -179.60(18) . . . .
C19 C18 O2 C17 -67.1(3) . . . .
C20 C18 O2 C17 57.3(3) . . . .
C21 C18 O2 C17 174.51(19) . . . .
C2 C1 N1 C4 0.0(3) . . . .
C2 C1 N1 C17 -177.1(2) . . . .
C3 C4 N1 C1 -0.5(3) . . . .
C3 C4 N1 C17 176.4(2) . . . .
O1 C17 N1 C1 -8.7(3) . . . .
O2 C17 N1 C1 170.6(2) . . . .
O1 C17 N1 C4 174.8(2) . . . .
O2 C17 N1 C4 -5.9(3) . . . .
O3 C38 O4 C39 1.7(4) . . . .
N2 C38 O4 C39 -178.43(19) . . . .
C41 C39 O4 C38 -67.4(3) . . . .
C40 C39 O4 C38 174.2(2) . . . .
C42 C39 O4 C38 56.6(3) . . . .
C23 C22 N2 C25 -0.3(3) . . . .
C23 C22 N2 C38 178.5(2) . . . .
C24 C25 N2 C22 0.3(3) . . . .
C24 C25 N2 C38 -178.7(2) . . . .
O3 C38 N2 C22 176.8(2) . . . .
O4 C38 N2 C22 -3.1(3) . . . .
O3 C38 N2 C25 -4.5(4) . . . .
O4 C38 N2 C25 175.6(2) . . . .
