#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/82/1518232.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_1518232
loop_
_publ_author_name
'Rives, Arnaud'
'Baglai, Iaroslav'
'Barthes, Cécile'
'Maraval, Valérie'
'Saffon-Merceron, Nathalie'
'Saquet, Alix'
'Voitenko, Zoia'
'Volovenko, Yulian'
'Chauvin, Remi'
_publ_section_title
;
 Carbo-cyclohexadienes vs. carbo-benzenes: structure and conjugative
 properties
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              1139
_journal_paper_doi               10.1039/C4SC02742F
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C48 H30 F6 O4'
_chemical_formula_sum            'C48 H30 F6 O4'
_chemical_formula_weight         784.75
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 100.1002(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.07527(8)
_cell_length_b                   16.18867(10)
_cell_length_c                   19.01027(12)
_cell_measurement_reflns_used    26323
_cell_measurement_temperature    105
_cell_measurement_theta_max      70
_cell_measurement_theta_min      4
_cell_volume                     3961.57(4)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      105
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35692
_diffrn_reflns_theta_full        70.120
_diffrn_reflns_theta_max         70.120
_diffrn_reflns_theta_min         4.388
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, acta cryst. (1995), a51, 33-38'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9834
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.0004958
_refine_ls_shift/su_mean         0.0000492
_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: 
 11.7 9.83 9.56 2.38 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0656
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0645
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3599
_reflns_number_total             3771
_reflns_threshold_expression     I>2.0σ(I)
_oxford_refine_ls_r_factor_ref   0.0485
_oxford_reflns_number_all        3754
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c4sc02742f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1518232--1518234.cif.'
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               1518232
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-x+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
F1 F 0.43152(7) 0.59853(5) 0.63780(5) 0.0434 1.0000 Uani .
F2 F 0.39843(8) 0.53138(6) 0.53901(5) 0.0479 1.0000 Uani .
F3 F 0.31370(7) 0.50467(5) 0.62349(5) 0.0409 1.0000 Uani .
C1 C 0.49615(10) 0.45415(8) 0.71831(7) 0.0264 1.0000 Uani .
C2 C 0.49008(10) 0.45922(8) 0.63972(7) 0.0261 1.0000 Uani .
C3 C 0.46115(10) 0.37908(7) 0.60532(6) 0.0257 1.0000 Uani .
C4 C 0.43707(9) 0.31523(7) 0.57520(6) 0.0238 1.0000 Uani .
C5 C 0.40795(9) 0.23960(7) 0.53786(7) 0.0225 1.0000 Uani .
C6 C 0.42131(9) 0.16826(7) 0.57536(6) 0.0230 1.0000 Uani .
C7 C 0.43377(9) 0.10150(7) 0.60781(6) 0.0223 1.0000 Uani .
C8 C 0.44709(9) 0.02871(7) 0.64356(6) 0.0210 1.0000 Uani .
C9 C 0.48474(9) 0.03026(7) 0.71830(7) 0.0221 1.0000 Uani .
C57 C 0.33726(11) 0.16841(8) 0.42341(7) 0.0314 1.0000 Uani .
C56 C 0.29640(12) 0.16946(9) 0.35162(7) 0.0345 1.0000 Uani .
C21 C 0.40650(11) 0.52498(8) 0.60903(8) 0.0311 1.0000 Uani .
C22 C 0.66937(12) 0.43933(10) 0.63982(9) 0.0421 1.0000 Uani .
C51 C 0.36605(9) 0.24194(8) 0.46095(7) 0.0233 1.0000 Uani .
C52 C 0.35387(10) 0.31613(8) 0.42323(7) 0.0282 1.0000 Uani .
C53 C 0.31146(11) 0.31770(9) 0.35064(7) 0.0319 1.0000 Uani .
C54 C 0.28129(10) 0.24453(9) 0.31515(7) 0.0294 1.0000 Uani .
C55 C 0.20020(16) 0.31199(12) 0.20849(8) 0.0526 1.0000 Uani .
C81 C 0.42209(9) -0.05183(7) 0.60786(6) 0.0220 1.0000 Uani .
C82 C 0.39330(10) -0.05719(8) 0.53389(7) 0.0296 1.0000 Uani .
C83 C 0.36729(11) -0.13270(10) 0.50141(8) 0.0363 1.0000 Uani .
C84 C 0.37117(10) -0.20433(9) 0.54167(8) 0.0352 1.0000 Uani .
C85 C 0.39867(12) -0.19982(9) 0.61530(9) 0.0378 1.0000 Uani .
C86 C 0.42333(11) -0.12413(8) 0.64823(7) 0.0316 1.0000 Uani .
O1 O 0.58189(7) 0.49208(6) 0.62205(5) 0.0321 1.0000 Uani .
O2 O 0.23675(9) 0.23796(7) 0.24475(5) 0.0394 1.0000 Uani .
H571 H 0.3450 0.1169 0.4476 0.0395 1.0000 Uiso R
H561 H 0.2783 0.1205 0.3270 0.0412 1.0000 Uiso R
H222 H 0.7267 0.4698 0.6277 0.0630 1.0000 Uiso R
H221 H 0.6816 0.4278 0.6886 0.0632 1.0000 Uiso R
H223 H 0.6605 0.3895 0.6122 0.0628 1.0000 Uiso R
H521 H 0.3742 0.3646 0.4472 0.0335 1.0000 Uiso R
H531 H 0.3044 0.3686 0.3262 0.0397 1.0000 Uiso R
H551 H 0.1637 0.2961 0.1619 0.0783 1.0000 Uiso R
H553 H 0.2591 0.3473 0.2043 0.0773 1.0000 Uiso R
H552 H 0.1535 0.3406 0.2346 0.0784 1.0000 Uiso R
H821 H 0.3930 -0.0099 0.5051 0.0366 1.0000 Uiso R
H831 H 0.3473 -0.1352 0.4509 0.0443 1.0000 Uiso R
H841 H 0.3555 -0.2564 0.5204 0.0425 1.0000 Uiso R
H851 H 0.3996 -0.2481 0.6435 0.0448 1.0000 Uiso R
H861 H 0.4406 -0.1210 0.6981 0.0395 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 0.0181 0.0091 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 0.0492 0.0322 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 0.3331 0.5567 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 0.0727 0.0534 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'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 '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
C1 6_656 C1 C2 . 176.38(10) yes
C1 . C2 C3 . 111.26(10) yes
C1 . C2 C21 . 108.89(10) yes
C3 . C2 C21 . 109.02(11) yes
C1 . C2 O1 . 111.35(10) yes
C3 . C2 O1 . 113.02(10) yes
C21 . C2 O1 . 102.90(10) yes
C2 . C3 C4 . 177.82(12) yes
C3 . C4 C5 . 178.90(12) yes
C4 . C5 C6 . 118.04(11) yes
C4 . C5 C51 . 119.42(10) yes
C6 . C5 C51 . 122.54(11) yes
C5 . C6 C7 . 177.99(12) yes
C6 . C7 C8 . 179.67(12) yes
C7 . C8 C9 . 118.53(10) yes
C7 . C8 C81 . 122.49(10) yes
C9 . C8 C81 . 118.97(10) yes
C8 . C9 C9 6_656 178.67(12) yes
C56 . C57 C51 . 121.08(12) yes
C56 . C57 H571 . 118.8 no
C51 . C57 H571 . 120.1 no
C57 . C56 C54 . 120.00(13) yes
C57 . C56 H561 . 120.6 no
C54 . C56 H561 . 119.4 no
C2 . C21 F3 . 110.95(10) yes
C2 . C21 F1 . 110.58(11) yes
F3 . C21 F1 . 107.70(11) yes
C2 . C21 F2 . 110.89(11) yes
F3 . C21 F2 . 108.23(12) yes
F1 . C21 F2 . 108.38(11) yes
O1 . C22 H222 . 105.4 no
O1 . C22 H221 . 110.3 no
H222 . C22 H221 . 109.6 no
O1 . C22 H223 . 111.1 no
H222 . C22 H223 . 109.0 no
H221 . C22 H223 . 111.1 no
C5 . C51 C57 . 120.23(11) yes
C5 . C51 C52 . 121.56(11) yes
C57 . C51 C52 . 118.20(12) yes
C51 . C52 C53 . 120.98(12) yes
C51 . C52 H521 . 118.8 no
C53 . C52 H521 . 120.3 no
C52 . C53 C54 . 119.74(12) yes
C52 . C53 H531 . 119.4 no
C54 . C53 H531 . 120.8 no
C56 . C54 C53 . 119.94(12) yes
C56 . C54 O2 . 114.67(12) yes
C53 . C54 O2 . 125.40(12) yes
O2 . C55 H551 . 106.8 no
O2 . C55 H553 . 109.4 no
H551 . C55 H553 . 110.7 no
O2 . C55 H552 . 110.0 no
H551 . C55 H552 . 110.1 no
H553 . C55 H552 . 109.8 no
C8 . C81 C82 . 121.11(11) yes
C8 . C81 C86 . 120.36(11) yes
C82 . C81 C86 . 118.49(11) yes
C81 . C82 C83 . 120.45(13) yes
C81 . C82 H821 . 120.6 no
C83 . C82 H821 . 118.9 no
C82 . C83 C84 . 120.68(13) yes
C82 . C83 H831 . 119.4 no
C84 . C83 H831 . 120.0 no
C83 . C84 C85 . 119.48(12) yes
C83 . C84 H841 . 121.8 no
C85 . C84 H841 . 118.7 no
C84 . C85 C86 . 120.07(13) yes
C84 . C85 H851 . 120.3 no
C86 . C85 H851 . 119.6 no
C81 . C86 C85 . 120.80(13) yes
C81 . C86 H861 . 119.2 no
C85 . C86 H861 . 120.0 no
C22 . O1 C2 . 113.66(11) yes
C55 . O2 C54 . 117.26(12) 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
F1 C21 . 1.3272(17) yes
F2 C21 . 1.3207(17) yes
F3 C21 . 1.3315(17) yes
C1 C1 6_656 1.191(3) yes
C1 C2 . 1.4846(17) yes
C2 C3 . 1.4720(17) yes
C2 C21 . 1.5635(18) yes
C2 O1 . 1.4065(15) yes
C3 C4 . 1.1967(18) yes
C4 C5 . 1.4330(17) yes
C5 C6 . 1.3523(17) yes
C5 C51 . 1.4692(17) yes
C6 C7 . 1.2409(18) yes
C7 C8 . 1.3561(17) yes
C8 C9 . 1.4201(16) yes
C8 C81 . 1.4796(16) yes
C9 C9 6_656 1.201(3) yes
C57 C56 . 1.3757(19) yes
C57 C51 . 1.4049(18) yes
C57 H571 . 0.948 no
C56 C54 . 1.3960(19) yes
C56 H561 . 0.929 no
C22 O1 . 1.4200(18) yes
C22 H222 . 0.958 no
C22 H221 . 0.932 no
C22 H223 . 0.958 no
C51 C52 . 1.3935(17) yes
C52 C53 . 1.3943(19) yes
C52 H521 . 0.923 no
C53 C54 . 1.386(2) yes
C53 H531 . 0.942 no
C54 O2 . 1.3669(17) yes
C55 O2 . 1.4228(19) yes
C55 H551 . 0.964 no
C55 H553 . 0.973 no
C55 H552 . 0.970 no
C81 C82 . 1.3932(17) yes
C81 C86 . 1.3982(18) yes
C82 C83 . 1.3848(19) yes
C82 H821 . 0.941 no
C83 C84 . 1.386(2) yes
C83 H831 . 0.951 no
C84 C85 . 1.385(2) yes
C84 H841 . 0.942 no
C85 C86 . 1.3879(19) yes
C85 H851 . 0.947 no
C86 H861 . 0.937 no
