#------------------------------------------------------------------------------
#$Date: 2018-09-02 03:38:27 +0300 (Sun, 02 Sep 2018) $
#$Revision: 210340 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/23/1502353.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_1502353
loop_
_publ_author_name
'Zöphel, Lukas'
'Enkelmann, Volker'
'Rieger, Ralph'
'Müllen, Klaus'
_publ_section_title
;
 Saddle Shaped Hexaaryl[a,c,fg,j,l,op]tetracenes from
 4,5,9,10-Tetrafunctionalized Pyrenes
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   17
_journal_name_full               'Organic Letters'
_journal_page_first              4506
_journal_page_last               4509
_journal_paper_doi               10.1021/ol2016516
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C10 H3 F6 O6 S2'
_chemical_formula_sum            'C10 H3 F6 O6 S2'
_chemical_formula_weight         397.25
_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
_audit_creation_date             09-08-25
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                101.515(3)
_cell_angle_beta                 96.482(3)
_cell_angle_gamma                97.466(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0041(2)
_cell_length_b                   9.4388(5)
_cell_length_c                   14.0451(8)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     637.91(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9295
_diffrn_reflns_theta_full        28.765
_diffrn_reflns_theta_max         29.964
_diffrn_reflns_theta_min         2.943
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_description       prism
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0750
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000311
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;

 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 

 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 

 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 

 Method = Robust Weighting (Prince, 1982) 

 W = [weight] * [1-(deltaF/6*sigmaF)²]² 

 Ai are: 

 1.33 0.433 0.899 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0485
_refine_ls_wR_factor_gt          0.0444
_refine_ls_wR_factor_ref         0.0444
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2767
_reflns_number_total             3668
_reflns_threshold_expression     I>3.0σ(I)
_oxford_diffrn_Wilson_scale      0.00
_cod_data_source_file            ol2016516_si_003.cif
_cod_data_source_block           zoep2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1502353
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
S1 S 0.40230(9) -0.49569(5) -0.18811(3) 0.0173 1.0000 Uani .
S2 S 0.72293(9) 0.07616(5) 0.35121(3) 0.0177 1.0000 Uani .
F1 F -0.0012(3) -0.48018(14) -0.31935(10) 0.0270 1.0000 Uani .
F2 F 0.0618(3) -0.69904(13) -0.30828(10) 0.0323 1.0000 Uani .
F3 F 0.3348(3) -0.57043(15) -0.37887(9) 0.0320 1.0000 Uani .
F4 F 0.4163(3) 0.27674(14) 0.39843(10) 0.0292 1.0000 Uani .
F5 F 0.5415(3) 0.16699(15) 0.51326(9) 0.0333 1.0000 Uani .
F6 F 0.8283(3) 0.32964(15) 0.47395(10) 0.0336 1.0000 Uani .
O1 O 0.5372(3) -0.34124(13) -0.20592(9) 0.0171 1.0000 Uani .
O2 O 0.6063(3) -0.58580(16) -0.18679(12) 0.0252 1.0000 Uani .
O3 O 0.2333(3) -0.47320(15) -0.11402(11) 0.0229 1.0000 Uani .
O4 O 0.8141(3) 0.17001(14) 0.27339(9) 0.0173 1.0000 Uani .
O5 O 0.4892(3) -0.02796(15) 0.30850(10) 0.0230 1.0000 Uani .
O6 O 0.9602(3) 0.03959(18) 0.39870(11) 0.0261 1.0000 Uani .
C1 C 0.5947(3) -0.04321(18) 0.01685(12) 0.0140 1.0000 Uani .
C2 C 0.6428(3) -0.17255(18) -0.04551(12) 0.0146 1.0000 Uani .
C3 C 0.8368(4) -0.25338(19) -0.01273(13) 0.0171 1.0000 Uani .
C4 C 0.9812(4) -0.2068(2) 0.08153(13) 0.0177 1.0000 Uani .
C5 C 0.9303(4) -0.08353(19) 0.14521(13) 0.0169 1.0000 Uani .
C6 C 0.7362(3) -0.00146(18) 0.11423(12) 0.0144 1.0000 Uani .
C7 C 0.4928(3) -0.21282(18) -0.14303(12) 0.0153 1.0000 Uani .
C8 C 0.6787(3) 0.12749(18) 0.17651(12) 0.0152 1.0000 Uani .
C9 C 0.1843(4) -0.5653(2) -0.30714(14) 0.0219 1.0000 Uani .
C10 C 0.6189(4) 0.2231(2) 0.44004(14) 0.0237 1.0000 Uani .
H31 H 0.8689 -0.3398 -0.0548 0.0213 1.0000 Uiso R
H41 H 1.1169 -0.2600 0.1025 0.0222 1.0000 Uiso R
H51 H 1.0272 -0.0548 0.2099 0.0210 1.0000 Uiso R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . S1 O2 . 107.86(8) yes
O1 . S1 O3 . 110.00(8) yes
O2 . S1 O3 . 123.03(9) yes
O1 . S1 C9 . 99.00(8) yes
O2 . S1 C9 . 105.78(9) yes
O3 . S1 C9 . 108.44(9) yes
O4 . S2 O5 . 110.00(8) yes
O4 . S2 O6 . 107.73(8) yes
O5 . S2 O6 . 123.15(9) yes
O4 . S2 C10 . 98.56(8) yes
O5 . S2 C10 . 108.29(9) yes
O6 . S2 C10 . 106.27(9) yes
S1 . O1 C7 . 118.02(11) yes
S2 . O4 C8 . 118.12(11) yes
C1 2_655 C1 C2 . 120.83(19) yes
C1 2_655 C1 C6 . 120.30(19) yes
C2 . C1 C6 . 118.87(15) yes
C1 . C2 C3 . 120.23(16) yes
C1 . C2 C7 . 117.38(15) yes
C3 . C2 C7 . 122.36(16) yes
C2 . C3 C4 . 119.79(16) yes
C2 . C3 H31 . 120.0 no
C4 . C3 H31 . 120.2 no
C3 . C4 C5 . 121.00(16) yes
C3 . C4 H41 . 119.4 no
C5 . C4 H41 . 119.6 no
C4 . C5 C6 . 120.19(16) yes
C4 . C5 H51 . 119.9 no
C6 . C5 H51 . 119.9 no
C1 . C6 C5 . 119.82(15) yes
C1 . C6 C8 . 117.77(15) yes
C5 . C6 C8 . 122.39(15) yes
C2 . C7 O1 . 118.20(14) yes
C2 . C7 C8 2_655 121.80(15) yes
O1 . C7 C8 2_655 119.93(15) yes
C6 . C8 O4 . 118.76(15) yes
C6 . C8 C7 2_655 121.77(15) yes
O4 . C8 C7 2_655 119.40(15) yes
S1 . C9 F2 . 107.98(13) yes
S1 . C9 F1 . 110.60(13) yes
F2 . C9 F1 . 109.48(16) yes
S1 . C9 F3 . 109.77(13) yes
F2 . C9 F3 . 109.57(16) yes
F1 . C9 F3 . 109.42(16) yes
S2 . C10 F6 . 109.63(14) yes
S2 . C10 F4 . 110.75(13) yes
F6 . C10 F4 . 109.21(17) yes
S2 . C10 F5 . 107.84(14) yes
F6 . C10 F5 . 109.45(16) yes
F4 . C10 F5 . 109.94(17) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.6036(13) yes
S1 O2 . 1.4121(14) yes
S1 O3 . 1.4145(14) yes
S1 C9 . 1.839(2) yes
S2 O4 . 1.6066(13) yes
S2 O5 . 1.4147(14) yes
S2 O6 . 1.4117(15) yes
S2 C10 . 1.843(2) yes
F1 C9 . 1.322(2) yes
F2 C9 . 1.326(2) yes
F3 C9 . 1.321(2) yes
F4 C10 . 1.320(2) yes
F5 C10 . 1.320(2) yes
F6 C10 . 1.326(2) yes
O1 C7 . 1.409(2) yes
O4 C8 . 1.405(2) yes
C1 C1 2_655 1.429(3) yes
C1 C2 . 1.419(2) yes
C1 C6 . 1.422(2) yes
C2 C3 . 1.403(2) yes
C2 C7 . 1.439(2) yes
C3 C4 . 1.392(3) yes
C3 H31 . 0.950 no
C4 C5 . 1.390(2) yes
C4 H41 . 0.950 no
C5 C6 . 1.403(2) yes
C5 H51 . 0.950 no
C6 C8 . 1.432(2) yes
C7 C8 2_655 1.359(2) yes
