#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/61/1506128.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_1506128
loop_
_publ_author_name
'Würthner, Frank'
'Osswald, Peter'
'Schmidt, Rüdiger'
'Kaiser, Theo E.'
'Mansikkamäki, Heidi'
'Könemann, Martin'
_publ_section_title
;
 Synthesis and optical and electrochemical properties of core-fluorinated
 perylene bisimides.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3765
_journal_page_last               3768
_journal_paper_doi               10.1021/ol0613416
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C48 H40 O4 N2 F2, 2(C7 H8)'
_chemical_formula_sum            'C62 H56 F2 N2 O4'
_chemical_formula_weight         931.09
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.135(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.040(2)
_cell_length_b                   11.320(1)
_cell_length_c                   25.137(2)
_cell_measurement_temperature    103(2)
_cell_volume                     4811.2(8)
_computing_molecular_graphics    'Mercury 1.4.1, ccdc'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker AXS CCD'
_diffrn_measurement_method       'rotation in phi and omega'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28605
_diffrn_reflns_theta_full        57.44
_diffrn_reflns_theta_max         57.44
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.9352
_exptl_absorpt_correction_T_min  0.7729
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_recrystallization_method
'Cooling of toluene solution to -30°C'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00376(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         6387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0519
_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)+(0.0516P)²+2.3971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                4828
_reflns_number_total             6387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0613416si1.cif
_cod_data_source_block           2a
_cod_original_cell_volume        4811.3(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1506128
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.17430(15) 0.5468(2) 0.35198(9) 0.0280(6) Uani 1 1 d . . .
C2 C 0.25636(15) 0.5360(2) 0.35972(10) 0.0306(6) Uani 1 1 d . . .
C3 C 0.29031(16) 0.4463(2) 0.33212(10) 0.0338(7) Uani 1 1 d . . .
H3 H 0.3462 0.4380 0.3362 0.041 Uiso 1 1 calc R . .
C4 C 0.24433(17) 0.3696(2) 0.29899(10) 0.0361(7) Uani 1 1 d . . .
H4 H 0.2684 0.3079 0.2811 0.043 Uiso 1 1 calc R . .
C5 C 0.16325(16) 0.3827(2) 0.29193(10) 0.0339(7) Uani 1 1 d . . .
H5 H 0.1320 0.3293 0.2691 0.041 Uiso 1 1 calc R . .
C6 C 0.12603(15) 0.4724(2) 0.31746(10) 0.0310(6) Uani 1 1 d . . .
N7 N 0.13696(12) 0.63843(16) 0.38130(8) 0.0275(5) Uani 1 1 d . . .
C8 C 0.13788(15) 0.7546(2) 0.36208(11) 0.0293(6) Uani 1 1 d . . .
C9 C 0.10101(14) 0.8468(2) 0.39309(10) 0.0270(6) Uani 1 1 d . . .
C10 C 0.06886(14) 0.8188(2) 0.44087(9) 0.0244(6) Uani 1 1 d . . .
C11 C 0.07054(14) 0.7003(2) 0.45866(10) 0.0261(6) Uani 1 1 d . . .
C12 C 0.10508(15) 0.6055(2) 0.42824(10) 0.0281(6) Uani 1 1 d . . .
C13 C 0.03793(15) 0.6726(2) 0.50441(10) 0.0303(6) Uani 1 1 d . . .
H13 H 0.0382 0.5929 0.5162 0.036 Uiso 1 1 calc R . .
C14 C 0.00452(15) 0.7592(2) 0.53369(10) 0.0300(6) Uani 1 1 d . . .
H14 H -0.0178 0.7370 0.5650 0.036 Uiso 0.25 1 calc PR A 1
F1 F 0.05860(11) 1.15497(14) 0.37866(7) 0.0348(5) Uani 0.75 1 d P B 2
C15 C 0.00271(14) 0.8777(2) 0.51845(10) 0.0261(6) Uani 1 1 d . . .
C16 C 0.03471(14) 0.9093(2) 0.47027(9) 0.0253(6) Uani 1 1 d . . .
C17 C 0.03197(14) 1.0287(2) 0.45085(10) 0.0263(6) Uani 1 1 d . . .
C18 C 0.06239(15) 1.0467(2) 0.40257(10) 0.0310(6) Uani 1 1 d . . .
H18 H 0.0593 1.1242 0.3880 0.037 Uiso 0.75 1 calc PR C 1
F1B F -0.0151(4) 0.7258(6) 0.5786(3) 0.0607(19) Uani 0.25 1 d P D 2
C19 C 0.09668(15) 0.9603(2) 0.37443(10) 0.0308(6) Uani 1 1 d . . .
H19 H 0.1173 0.9797 0.3421 0.037 Uiso 1 1 calc R . .
C21 C 0.31024(15) 0.6159(2) 0.39675(10) 0.0341(7) Uani 1 1 d . . .
H21 H 0.2764 0.6758 0.4122 0.041 Uiso 1 1 calc R . .
C22 C 0.36882(16) 0.6821(2) 0.36608(11) 0.0434(7) Uani 1 1 d . . .
H22A H 0.4023 0.7333 0.3909 0.065 Uiso 1 1 calc R . .
H22B H 0.3397 0.7304 0.3379 0.065 Uiso 1 1 calc R . .
H22C H 0.4020 0.6251 0.3498 0.065 Uiso 1 1 calc R . .
C23 C 0.35343(17) 0.5450(2) 0.44312(11) 0.0459(8) Uani 1 1 d . . .
H23A H 0.3870 0.5980 0.4669 0.069 Uiso 1 1 calc R . .
H23B H 0.3863 0.4844 0.4289 0.069 Uiso 1 1 calc R . .
H23C H 0.3147 0.5070 0.4633 0.069 Uiso 1 1 calc R . .
C61 C 0.03746(15) 0.4908(2) 0.30459(10) 0.0334(7) Uani 1 1 d . . .
H61 H 0.0189 0.5358 0.3349 0.040 Uiso 1 1 calc R . .
C62 C 0.02130(18) 0.5660(3) 0.25414(13) 0.0639(10) Uani 1 1 d . . .
H62A H -0.0358 0.5778 0.2455 0.096 Uiso 1 1 calc R . .
H62B H 0.0419 0.5257 0.2243 0.096 Uiso 1 1 calc R . .
H62C H 0.0474 0.6427 0.2602 0.096 Uiso 1 1 calc R . .
C63 C -0.00870(19) 0.3762(3) 0.29824(16) 0.0673(10) Uani 1 1 d . . .
H63A H -0.0653 0.3936 0.2902 0.101 Uiso 1 1 calc R . .
H63B H 0.0006 0.3307 0.3316 0.101 Uiso 1 1 calc R . .
H63C H 0.0087 0.3301 0.2688 0.101 Uiso 1 1 calc R . .
O1 O 0.16823(11) 0.77743(14) 0.32192(7) 0.0374(5) Uani 1 1 d . . .
O2 O 0.10722(11) 0.50257(15) 0.44268(7) 0.0389(5) Uani 1 1 d . . .
C201 C 0.31727(15) 1.3514(2) 0.68680(10) 0.0293(6) Uani 1 1 d . . .
C202 C 0.23645(15) 1.3763(2) 0.67930(10) 0.0308(6) Uani 1 1 d . . .
C221 C 0.18176(16) 1.3346(2) 0.63066(11) 0.0371(7) Uani 1 1 d . . .
H221 H 0.2153 1.2971 0.6054 0.045 Uiso 1 1 calc R . .
C222 C 0.12463(17) 1.2402(2) 0.64644(12) 0.0493(8) Uani 1 1 d . . .
H22D H 0.1548 1.1750 0.6646 0.074 Uiso 1 1 calc R . .
H22E H 0.0925 1.2104 0.6142 0.074 Uiso 1 1 calc R . .
H22F H 0.0900 1.2748 0.6706 0.074 Uiso 1 1 calc R . .
C223 C 0.13721(17) 1.4372(2) 0.60100(11) 0.0452(8) Uani 1 1 d . . .
H22G H 0.1037 1.4069 0.5694 0.068 Uiso 1 1 calc R . .
H22H H 0.1753 1.4939 0.5896 0.068 Uiso 1 1 calc R . .
H22I H 0.1042 1.4764 0.6249 0.068 Uiso 1 1 calc R . .
C203 C 0.20693(16) 1.4430(2) 0.71908(11) 0.0364(7) Uani 1 1 d . . .
H203 H 0.1521 1.4612 0.7156 0.044 Uiso 1 1 calc R . .
C204 C 0.25548(18) 1.4832(2) 0.76340(11) 0.0383(7) Uani 1 1 d . . .
H204 H 0.2340 1.5288 0.7898 0.046 Uiso 1 1 calc R . .
C205 C 0.33483(17) 1.4572(2) 0.76931(11) 0.0366(7) Uani 1 1 d . . .
H205 H 0.3678 1.4860 0.7998 0.044 Uiso 1 1 calc R . .
C206 C 0.36802(15) 1.3891(2) 0.73131(10) 0.0319(7) Uani 1 1 d . . .
C261 C 0.45521(15) 1.3579(2) 0.74048(11) 0.0372(7) Uani 1 1 d . . .
H261 H 0.4672 1.3079 0.7097 0.045 Uiso 1 1 calc R . .
C262 C 0.47361(18) 1.2847(3) 0.79182(12) 0.0502(8) Uani 1 1 d . . .
H26A H 0.4403 1.2138 0.7894 0.075 Uiso 1 1 calc R . .
H26B H 0.4628 1.3320 0.8227 0.075 Uiso 1 1 calc R . .
H26C H 0.5294 1.2615 0.7962 0.075 Uiso 1 1 calc R . .
C263 C 0.50647(17) 1.4682(3) 0.74151(12) 0.0497(8) Uani 1 1 d . . .
H26D H 0.4943 1.5112 0.7076 0.075 Uiso 1 1 calc R . .
H26E H 0.5624 1.4454 0.7462 0.075 Uiso 1 1 calc R . .
H26F H 0.4957 1.5190 0.7713 0.075 Uiso 1 1 calc R . .
N207 N 0.35018(12) 1.27981(17) 0.64653(8) 0.0277(5) Uani 1 1 d . . .
C208 C 0.38197(15) 1.3393(2) 0.60528(10) 0.0309(6) Uani 1 1 d . . .
C209 C 0.41805(14) 1.2637(2) 0.56649(10) 0.0273(6) Uani 1 1 d . . .
C210 C 0.42283(14) 1.1404(2) 0.57261(10) 0.0262(6) Uani 1 1 d . . .
C211 C 0.38799(14) 1.0855(2) 0.61476(10) 0.0280(6) Uani 1 1 d . . .
C212 C 0.35049(15) 1.1576(2) 0.65361(10) 0.0300(6) Uani 1 1 d . . .
C213 C 0.38864(15) 0.9651(2) 0.61952(10) 0.0314(6) Uani 1 1 d . . .
H213 H 0.3633 0.9284 0.6468 0.038 Uiso 1 1 calc R . .
C214 C 0.42645(15) 0.8963(2) 0.58436(10) 0.0327(7) Uani 1 1 d . . .
H214 H 0.4264 0.8129 0.5884 0.039 Uiso 0.75 1 calc PR E 1
F20B F 0.4275(4) 0.7788(5) 0.5926(3) 0.0553(18) Uani 0.25 1 d P F 2
C215 C 0.46423(14) 0.9451(2) 0.54349(10) 0.0288(6) Uani 1 1 d . . .
C216 C 0.46126(14) 1.0702(2) 0.53624(9) 0.0276(6) Uani 1 1 d . . .
C217 C 0.49425(14) 1.1274(2) 0.49298(10) 0.0279(6) Uani 1 1 d . . .
C219 C 0.44805(15) 1.3169(2) 0.52442(10) 0.0324(7) Uani 1 1 d . . .
H219 H 0.4443 1.4001 0.5198 0.039 Uiso 1 1 calc R . .
O201 O 0.32167(11) 1.11415(15) 0.69113(7) 0.0430(5) Uani 1 1 d . . .
O202 O 0.38001(11) 1.44618(15) 0.60232(7) 0.0427(5) Uani 1 1 d . . .
C218 C 0.48395(15) 1.2484(2) 0.48859(10) 0.0319(7) Uani 1 1 d . . .
H218 H 0.5027 1.2870 0.4591 0.038 Uiso 0.25 1 calc PR G 1
F201 F 0.50952(12) 1.31019(16) 0.44752(8) 0.0431(5) Uani 0.75 1 d P H 2
C101 C 0.32215(16) 0.9542(2) 0.41856(11) 0.0428(7) Uani 1 1 d . . .
H10A H 0.2878 0.9222 0.3878 0.064 Uiso 1 1 calc R . .
H10B H 0.3350 0.8916 0.4452 0.064 Uiso 1 1 calc R . .
H10C H 0.3710 0.9842 0.4066 0.064 Uiso 1 1 calc R . .
C103 C 0.26582(17) 1.1598(2) 0.41634(11) 0.0412(7) Uani 1 1 d . . .
H103 H 0.2835 1.1706 0.3823 0.049 Uiso 1 1 calc R . .
C102 C 0.28023(15) 1.0531(2) 0.44327(11) 0.0349(7) Uani 1 1 d . . .
C104 C 0.22596(17) 1.2506(2) 0.43852(12) 0.0447(8) Uani 1 1 d . . .
H104 H 0.2161 1.3226 0.4194 0.054 Uiso 1 1 calc R . .
C105 C 0.20046(17) 1.2368(2) 0.48827(12) 0.0422(7) Uani 1 1 d . . .
H105 H 0.1737 1.2994 0.5036 0.051 Uiso 1 1 calc R . .
C106 C 0.21421(16) 1.1310(2) 0.51554(11) 0.0409(7) Uani 1 1 d . . .
H106 H 0.1964 1.1205 0.5496 0.049 Uiso 1 1 calc R . .
C107 C 0.25398(15) 1.0407(2) 0.49315(11) 0.0379(7) Uani 1 1 d . . .
H107 H 0.2635 0.9688 0.5123 0.045 Uiso 1 1 calc R . .
C111 C 0.26558(18) 0.6845(3) 0.54855(11) 0.0479(8) Uani 1 1 d . . .
H11A H 0.2174 0.6477 0.5305 0.072 Uiso 1 1 calc R . .
H11B H 0.3067 0.6242 0.5563 0.072 Uiso 1 1 calc R . .
H11C H 0.2840 0.7453 0.5253 0.072 Uiso 1 1 calc R . .
C112 C 0.24801(17) 0.7402(2) 0.60030(11) 0.0393(7) Uani 1 1 d . . .
C113 C 0.28469(17) 0.7004(2) 0.64954(11) 0.0429(8) Uani 1 1 d . . .
H113 H 0.3205 0.6358 0.6509 0.051 Uiso 1 1 calc R . .
C114 C 0.26919(19) 0.7544(3) 0.69690(12) 0.0501(8) Uani 1 1 d . . .
H114 H 0.2948 0.7264 0.7302 0.060 Uiso 1 1 calc R . .
C115 C 0.2176(2) 0.8474(3) 0.69610(14) 0.0542(9) Uani 1 1 d . . .
H115 H 0.2079 0.8845 0.7286 0.065 Uiso 1 1 calc R . .
C116 C 0.17977(18) 0.8864(3) 0.64750(14) 0.0512(8) Uani 1 1 d . . .
H116 H 0.1429 0.9496 0.6465 0.061 Uiso 1 1 calc R . .
C117 C 0.19538(16) 0.8338(2) 0.60020(12) 0.0434(8) Uani 1 1 d . . .
H117 H 0.1696 0.8624 0.5670 0.052 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
C2 C1 C6 122.4(2) .
C2 C1 N7 118.9(2) .
C6 C1 N7 118.7(2) .
C1 C2 C3 117.7(2) .
C1 C2 C21 123.5(2) .
C3 C2 C21 118.7(2) .
C4 C3 C2 121.3(3) .
C4 C3 H3 119.3 .
C2 C3 H3 119.3 .
C3 C4 C5 119.7(2) .
C3 C4 H4 120.2 .
C5 C4 H4 120.2 .
C4 C5 C6 121.7(2) .
C4 C5 H5 119.2 .
C6 C5 H5 119.2 .
C5 C6 C1 117.2(2) .
C5 C6 C61 119.9(2) .
C1 C6 C61 122.8(2) .
C8 N7 C12 124.0(2) .
C8 N7 C1 117.86(19) .
C12 N7 C1 118.11(18) .
O1 C8 N7 120.6(2) .
O1 C8 C9 122.4(2) .
N7 C8 C9 117.0(2) .
C19 C9 C10 119.4(2) .
C19 C9 C8 119.2(2) .
C10 C9 C8 121.3(2) .
C11 C10 C9 119.1(2) .
C11 C10 C16 120.7(2) .
C9 C10 C16 120.2(2) .
C13 C11 C10 119.1(2) .
C13 C11 C12 119.7(2) .
C10 C11 C12 121.2(2) .
O2 C12 N7 120.1(2) .
O2 C12 C11 122.5(2) .
N7 C12 C11 117.4(2) .
C11 C13 C14 121.2(2) .
C11 C13 H13 119.4 .
C14 C13 H13 119.4 .
C13 C14 C15 122.0(2) .
C13 C14 H14 119.0 .
C15 C14 H14 119.0 .
C14 C15 C16 118.3(2) .
C14 C15 C17 122.9(2) 3_576
C16 C15 C17 118.8(2) 3_576
C10 C16 C15 118.7(2) .
C10 C16 C17 119.8(2) .
C15 C16 C17 121.5(2) .
C18 C17 C16 115.7(2) .
C18 C17 C15 124.6(2) 3_576
C16 C17 C15 119.7(2) 3_576
C19 C18 C17 124.8(2) .
C19 C18 H18 117.6 .
C17 C18 H18 117.6 .
C9 C19 C18 119.9(2) .
C9 C19 H19 120.0 .
C18 C19 H19 120.0 .
C2 C21 C23 110.6(2) .
C2 C21 C22 111.4(2) .
C23 C21 C22 111.1(2) .
C2 C21 H21 107.9 .
C23 C21 H21 107.9 .
C22 C21 H21 107.9 .
C21 C22 H22A 109.5 .
C21 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C21 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C21 C23 H23A 109.5 .
C21 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C21 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C63 C61 C6 113.2(2) .
C63 C61 C62 110.6(3) .
C6 C61 C62 109.0(2) .
C63 C61 H61 107.9 .
C6 C61 H61 107.9 .
C62 C61 H61 107.9 .
C61 C62 H62A 109.5 .
C61 C62 H62B 109.5 .
H62A C62 H62B 109.5 .
C61 C62 H62C 109.5 .
H62A C62 H62C 109.5 .
H62B C62 H62C 109.5 .
C61 C63 H63A 109.5 .
C61 C63 H63B 109.5 .
H63A C63 H63B 109.5 .
C61 C63 H63C 109.5 .
H63A C63 H63C 109.5 .
H63B C63 H63C 109.5 .
C206 C201 C202 123.4(2) .
C206 C201 N207 118.2(2) .
C202 C201 N207 118.4(2) .
C201 C202 C203 116.7(2) .
C201 C202 C221 122.9(2) .
C203 C202 C221 120.4(2) .
C202 C221 C223 112.0(2) .
C202 C221 C222 110.8(2) .
C223 C221 C222 111.3(2) .
C202 C221 H221 107.5 .
C223 C221 H221 107.5 .
C222 C221 H221 107.5 .
C221 C222 H22D 109.5 .
C221 C222 H22E 109.5 .
H22D C222 H22E 109.5 .
C221 C222 H22F 109.5 .
H22D C222 H22F 109.5 .
H22E C222 H22F 109.5 .
C221 C223 H22G 109.5 .
C221 C223 H22H 109.5 .
H22G C223 H22H 109.5 .
C221 C223 H22I 109.5 .
H22G C223 H22I 109.5 .
H22H C223 H22I 109.5 .
C204 C203 C202 121.6(3) .
C204 C203 H203 119.2 .
C202 C203 H203 119.2 .
C205 C204 C203 120.0(2) .
C205 C204 H204 120.0 .
C203 C204 H204 120.0 .
C204 C205 C206 121.3(3) .
C204 C205 H205 119.3 .
C206 C205 H205 119.3 .
C201 C206 C205 117.0(2) .
C201 C206 C261 123.3(2) .
C205 C206 C261 119.7(2) .
C206 C261 C263 111.1(2) .
C206 C261 C262 110.4(2) .
C263 C261 C262 111.8(2) .
C206 C261 H261 107.8 .
C263 C261 H261 107.8 .
C262 C261 H261 107.8 .
C261 C262 H26A 109.5 .
C261 C262 H26B 109.5 .
H26A C262 H26B 109.5 .
C261 C262 H26C 109.5 .
H26A C262 H26C 109.5 .
H26B C262 H26C 109.5 .
C261 C263 H26D 109.5 .
C261 C263 H26E 109.5 .
H26D C263 H26E 109.5 .
C261 C263 H26F 109.5 .
H26D C263 H26F 109.5 .
H26E C263 H26F 109.5 .
C212 N207 C208 125.2(2) .
C212 N207 C201 117.19(19) .
C208 N207 C201 117.59(19) .
O202 C208 N207 121.0(2) .
O202 C208 C209 123.0(2) .
N207 C208 C209 116.0(2) .
C219 C209 C210 119.9(2) .
C219 C209 C208 118.6(2) .
C210 C209 C208 121.5(2) .
C209 C210 C211 119.5(2) .
C209 C210 C216 120.5(2) .
C211 C210 C216 120.0(2) .
C213 C211 C210 120.1(2) .
C213 C211 C212 119.5(2) .
C210 C211 C212 120.4(2) .
O201 C212 N207 120.2(2) .
O201 C212 C211 122.5(2) .
N207 C212 C211 117.3(2) .
C211 C213 C214 120.0(2) .
C211 C213 H213 120.0 .
C214 C213 H213 120.0 .
C215 C214 C213 122.6(2) .
C215 C214 H214 118.7 .
C213 C214 H214 118.7 .
C214 C215 C216 118.4(2) .
C214 C215 C217 122.6(2) 3_676
C216 C215 C217 119.0(2) 3_676
C215 C216 C210 118.8(2) .
C215 C216 C217 122.2(2) .
C210 C216 C217 119.1(2) .
C218 C217 C216 116.6(2) .
C218 C217 C215 124.6(2) 3_676
C216 C217 C215 118.8(2) 3_676
C209 C219 C218 119.5(2) .
C209 C219 H219 120.3 .
C218 C219 H219 120.3 .
C217 C218 C219 124.3(2) .
C217 C218 H218 117.8 .
C219 C218 H218 117.8 .
C102 C101 H10A 109.5 .
C102 C101 H10B 109.5 .
H10A C101 H10B 109.5 .
C102 C101 H10C 109.5 .
H10A C101 H10C 109.5 .
H10B C101 H10C 109.5 .
C104 C103 C102 120.9(3) .
C104 C103 H103 119.6 .
C102 C103 H103 119.6 .
C107 C102 C103 118.0(2) .
C107 C102 C101 121.4(2) .
C103 C102 C101 120.6(2) .
C105 C104 C103 120.3(3) .
C105 C104 H104 119.8 .
C103 C104 H104 119.8 .
C104 C105 C106 119.5(3) .
C104 C105 H105 120.3 .
C106 C105 H105 120.3 .
C107 C106 C105 119.9(3) .
C107 C106 H106 120.1 .
C105 C106 H106 120.1 .
C106 C107 C102 121.4(2) .
C106 C107 H107 119.3 .
C102 C107 H107 119.3 .
C112 C111 H11A 109.5 .
C112 C111 H11B 109.5 .
H11A C111 H11B 109.5 .
C112 C111 H11C 109.5 .
H11A C111 H11C 109.5 .
H11B C111 H11C 109.5 .
C117 C112 C113 117.9(3) .
C117 C112 C111 121.0(3) .
C113 C112 C111 121.1(3) .
C112 C113 C114 120.4(3) .
C112 C113 H113 119.8 .
C114 C113 H113 119.8 .
C115 C114 C113 121.0(3) .
C115 C114 H114 119.5 .
C113 C114 H114 119.5 .
C114 C115 C116 119.1(3) .
C114 C115 H115 120.4 .
C116 C115 H115 120.4 .
C115 C116 C117 120.2(3) .
C115 C116 H116 119.9 .
C117 C116 H116 119.9 .
C116 C117 C112 121.3(3) .
C116 C117 H117 119.3 .
C112 C117 H117 119.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.393(4) .
C1 C6 1.400(3) .
C1 N7 1.463(3) .
C2 C3 1.395(3) .
C2 C21 1.522(4) .
C3 C4 1.379(4) .
C3 H3 0.9500 .
C4 C5 1.379(4) .
C4 H4 0.9500 .
C5 C6 1.395(3) .
C5 H5 0.9500 .
C6 C61 1.518(4) .
N7 C8 1.401(3) .
N7 C12 1.409(3) .
C8 O1 1.218(3) .
C8 C9 1.488(3) .
C9 C19 1.367(3) .
C9 C10 1.417(3) .
C10 C11 1.413(3) .
C10 C16 1.429(3) .
C11 C13 1.374(3) .
C11 C12 1.481(3) .
C12 O2 1.219(3) .
C13 C14 1.389(3) .
C13 H13 0.9500 .
C14 C15 1.395(3) .
C14 H14 0.9500 .
C15 C16 1.434(3) .
C15 C17 1.476(3) 3_576
C16 C17 1.435(3) .
C17 C18 1.393(3) .
C17 C15 1.476(3) 3_576
C18 C19 1.378(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C21 C23 1.527(4) .
C21 C22 1.531(4) .
C21 H21 1.0000 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C61 C63 1.515(4) .
C61 C62 1.524(4) .
C61 H61 1.0000 .
C62 H62A 0.9800 .
C62 H62B 0.9800 .
C62 H62C 0.9800 .
C63 H63A 0.9800 .
C63 H63B 0.9800 .
C63 H63C 0.9800 .
C201 C206 1.394(4) .
C201 C202 1.395(3) .
C201 N207 1.462(3) .
C202 C203 1.396(3) .
C202 C221 1.517(4) .
C221 C223 1.530(4) .
C221 C222 1.530(4) .
C221 H221 1.0000 .
C222 H22D 0.9800 .
C222 H22E 0.9800 .
C222 H22F 0.9800 .
C223 H22G 0.9800 .
C223 H22H 0.9800 .
C223 H22I 0.9800 .
C203 C204 1.379(4) .
C203 H203 0.9500 .
C204 C205 1.374(4) .
C204 H204 0.9500 .
C205 C206 1.400(3) .
C205 H205 0.9500 .
C206 C261 1.517(4) .
C261 C263 1.522(4) .
C261 C262 1.533(4) .
C261 H261 1.0000 .
C262 H26A 0.9800 .
C262 H26B 0.9800 .
C262 H26C 0.9800 .
C263 H26D 0.9800 .
C263 H26E 0.9800 .
C263 H26F 0.9800 .
N207 C212 1.395(3) .
N207 C208 1.401(3) .
C208 O202 1.212(3) .
C208 C209 1.486(3) .
C209 C219 1.370(3) .
C209 C210 1.406(3) .
C210 C211 1.421(3) .
C210 C216 1.430(3) .
C211 C213 1.368(3) .
C211 C212 1.478(3) .
C212 O201 1.220(3) .
C213 C214 1.394(3) .
C213 H213 0.9500 .
C214 C215 1.392(3) .
C214 H214 0.9500 .
C215 C216 1.428(3) .
C215 C217 1.475(3) 3_676
C216 C217 1.439(3) .
C217 C218 1.383(3) .
C217 C215 1.475(3) 3_676
C219 C218 1.387(3) .
C219 H219 0.9500 .
C218 H218 0.9500 .
C101 C102 1.504(4) .
C101 H10A 0.9800 .
C101 H10B 0.9800 .
C101 H10C 0.9800 .
C103 C104 1.387(4) .
C103 C102 1.391(4) .
C103 H103 0.9500 .
C102 C107 1.390(4) .
C104 C105 1.383(4) .
C104 H104 0.9500 .
C105 C106 1.385(4) .
C105 H105 0.9500 .
C106 C107 1.384(4) .
C106 H106 0.9500 .
C107 H107 0.9500 .
C111 C112 1.509(4) .
C111 H11A 0.9800 .
C111 H11B 0.9800 .
C111 H11C 0.9800 .
C112 C117 1.388(4) .
C112 C113 1.391(4) .
C113 C114 1.393(4) .
C113 H113 0.9500 .
C114 C115 1.370(4) .
C114 H114 0.9500 .
C115 C116 1.381(4) .
C115 H115 0.9500 .
C116 C117 1.385(4) .
C116 H116 0.9500 .
C117 H117 0.9500 .
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
C6 C1 C2 C3 -0.7(4) . .
N7 C1 C2 C3 178.7(2) . .
C6 C1 C2 C21 179.7(2) . .
N7 C1 C2 C21 -0.9(3) . .
C1 C2 C3 C4 -1.1(4) . .
C21 C2 C3 C4 178.5(2) . .
C2 C3 C4 C5 1.4(4) . .
C3 C4 C5 C6 0.1(4) . .
C4 C5 C6 C1 -1.9(4) . .
C4 C5 C6 C61 174.3(2) . .
C2 C1 C6 C5 2.2(4) . .
N7 C1 C6 C5 -177.3(2) . .
C2 C1 C6 C61 -173.9(2) . .
N7 C1 C6 C61 6.7(3) . .
C2 C1 N7 C8 78.9(3) . .
C6 C1 N7 C8 -101.7(3) . .
C2 C1 N7 C12 -98.7(3) . .
C6 C1 N7 C12 80.8(3) . .
C12 N7 C8 O1 178.1(2) . .
C1 N7 C8 O1 0.7(4) . .
C12 N7 C8 C9 -1.4(3) . .
C1 N7 C8 C9 -178.8(2) . .
O1 C8 C9 C19 3.9(4) . .
N7 C8 C9 C19 -176.6(2) . .
O1 C8 C9 C10 -177.5(2) . .
N7 C8 C9 C10 2.1(3) . .
C19 C9 C10 C11 177.3(2) . .
C8 C9 C10 C11 -1.3(4) . .
C19 C9 C10 C16 -2.2(4) . .
C8 C9 C10 C16 179.2(2) . .
C9 C10 C11 C13 -178.7(2) . .
C16 C10 C11 C13 0.8(4) . .
C9 C10 C11 C12 -0.1(4) . .
C16 C10 C11 C12 179.4(2) . .
C8 N7 C12 O2 -179.2(2) . .
C1 N7 C12 O2 -1.9(3) . .
C8 N7 C12 C11 0.1(3) . .
C1 N7 C12 C11 177.5(2) . .
C13 C11 C12 O2 -1.4(4) . .
C10 C11 C12 O2 -179.9(2) . .
C13 C11 C12 N7 179.3(2) . .
C10 C11 C12 N7 0.7(3) . .
C10 C11 C13 C14 -0.9(4) . .
C12 C11 C13 C14 -179.5(2) . .
C11 C13 C14 C15 -0.3(4) . .
C13 C14 C15 C16 1.6(4) . .
C13 C14 C15 C17 -179.6(2) . 3_576
C11 C10 C16 C15 0.5(3) . .
C9 C10 C16 C15 180.0(2) . .
C11 C10 C16 C17 -178.6(2) . .
C9 C10 C16 C17 0.9(3) . .
C14 C15 C16 C10 -1.7(3) . .
C17 C15 C16 C10 179.5(2) 3_576 .
C14 C15 C16 C17 177.4(2) . .
C17 C15 C16 C17 -1.5(4) 3_576 .
C10 C16 C17 C18 1.4(3) . .
C15 C16 C17 C18 -177.7(2) . .
C10 C16 C17 C15 -179.5(2) . 3_576
C15 C16 C17 C15 1.5(4) . 3_576
C16 C17 C18 C19 -2.6(4) . .
C15 C17 C18 C19 178.2(2) 3_576 .
C10 C9 C19 C18 1.1(4) . .
C8 C9 C19 C18 179.7(2) . .
C17 C18 C19 C9 1.5(4) . .
C1 C2 C21 C23 115.7(3) . .
C3 C2 C21 C23 -63.8(3) . .
C1 C2 C21 C22 -120.3(3) . .
C3 C2 C21 C22 60.2(3) . .
C5 C6 C61 C63 40.2(3) . .
C1 C6 C61 C63 -143.9(3) . .
C5 C6 C61 C62 -83.4(3) . .
C1 C6 C61 C62 92.5(3) . .
C206 C201 C202 C203 0.3(4) . .
N207 C201 C202 C203 178.9(2) . .
C206 C201 C202 C221 -180.0(2) . .
N207 C201 C202 C221 -1.4(3) . .
C201 C202 C221 C223 -124.2(3) . .
C203 C202 C221 C223 55.6(3) . .
C201 C202 C221 C222 110.9(3) . .
C203 C202 C221 C222 -69.3(3) . .
C201 C202 C203 C204 0.5(4) . .
C221 C202 C203 C204 -179.3(2) . .
C202 C203 C204 C205 -0.3(4) . .
C203 C204 C205 C206 -0.7(4) . .
C202 C201 C206 C205 -1.2(4) . .
N207 C201 C206 C205 -179.8(2) . .
C202 C201 C206 C261 177.5(2) . .
N207 C201 C206 C261 -1.1(3) . .
C204 C205 C206 C201 1.4(4) . .
C204 C205 C206 C261 -177.4(2) . .
C201 C206 C261 C263 117.9(3) . .
C205 C206 C261 C263 -63.4(3) . .
C201 C206 C261 C262 -117.4(3) . .
C205 C206 C261 C262 61.3(3) . .
C206 C201 N207 C212 89.5(3) . .
C202 C201 N207 C212 -89.2(3) . .
C206 C201 N207 C208 -87.8(3) . .
C202 C201 N207 C208 93.6(3) . .
C212 N207 C208 O202 -179.2(2) . .
C201 N207 C208 O202 -2.2(3) . .
C212 N207 C208 C209 0.4(3) . .
C201 N207 C208 C209 177.4(2) . .
O202 C208 C209 C219 -2.3(4) . .
N207 C208 C209 C219 178.2(2) . .
O202 C208 C209 C210 176.8(2) . .
N207 C208 C209 C210 -2.7(3) . .
C219 C209 C210 C211 -176.8(2) . .
C208 C209 C210 C211 4.1(4) . .
C219 C209 C210 C216 2.1(4) . .
C208 C209 C210 C216 -176.9(2) . .
C209 C210 C211 C213 176.6(2) . .
C216 C210 C211 C213 -2.3(4) . .
C209 C210 C211 C212 -3.1(4) . .
C216 C210 C211 C212 178.0(2) . .
C208 N207 C212 O201 179.5(2) . .
C201 N207 C212 O201 2.5(3) . .
C208 N207 C212 C211 0.6(4) . .
C201 N207 C212 C211 -176.5(2) . .
C213 C211 C212 O201 2.1(4) . .
C210 C211 C212 O201 -178.1(2) . .
C213 C211 C212 N207 -178.9(2) . .
C210 C211 C212 N207 0.8(3) . .
C210 C211 C213 C214 2.7(4) . .
C212 C211 C213 C214 -177.6(2) . .
C211 C213 C214 C215 -0.3(4) . .
C213 C214 C215 C216 -2.5(4) . .
C213 C214 C215 C217 178.6(2) . 3_676
C214 C215 C216 C210 2.8(3) . .
C217 C215 C216 C210 -178.3(2) 3_676 .
C214 C215 C216 C217 -176.0(2) . .
C217 C215 C216 C217 2.9(4) 3_676 .
C209 C210 C216 C215 -179.4(2) . .
C211 C210 C216 C215 -0.5(3) . .
C209 C210 C216 C217 -0.6(3) . .
C211 C210 C216 C217 178.3(2) . .
C215 C216 C217 C218 176.7(2) . .
C210 C216 C217 C218 -2.1(3) . .
C215 C216 C217 C215 -2.9(4) . 3_676
C210 C216 C217 C215 178.3(2) . 3_676
C210 C209 C219 C218 -0.9(4) . .
C208 C209 C219 C218 178.2(2) . .
C216 C217 C218 C219 3.5(4) . .
C215 C217 C218 C219 -176.9(2) 3_676 .
C209 C219 C218 C217 -2.1(4) . .
C104 C103 C102 C107 -0.4(4) . .
C104 C103 C102 C101 178.9(2) . .
C102 C103 C104 C105 0.6(4) . .
C103 C104 C105 C106 -0.8(4) . .
C104 C105 C106 C107 0.7(4) . .
C105 C106 C107 C102 -0.5(4) . .
C103 C102 C107 C106 0.4(4) . .
C101 C102 C107 C106 -178.9(2) . .
C117 C112 C113 C114 -0.7(4) . .
C111 C112 C113 C114 178.6(3) . .
C112 C113 C114 C115 0.2(4) . .
C113 C114 C115 C116 0.9(4) . .
C114 C115 C116 C117 -1.5(4) . .
C115 C116 C117 C112 0.9(4) . .
C113 C112 C117 C116 0.2(4) . .
C111 C112 C117 C116 -179.1(3) . .
