#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:19:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180500 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/69/7216984.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_7216984
loop_
_publ_author_name
'Perepichka, Igor F.'
'Perepichka, Dmitrii F.'
'Lyubchik, Svetlana B.'
'Bryce, Martin R.'
'Batsanov, Andrei S.'
'Howard, Judith A. K.'
_publ_section_title
;
 Electron acceptors of the fluorene series. Part 13.
 9-(5-Nitrofuran-2-ylidene)- and
 9-(5-nitro-2-thienylidene)-2,4,5,7-tetranitrofluorenes: novel π-extended
 electron acceptors. Synthesis, cyclic voltammetry and X-ray crystal
 structures for the acceptor and its 4,5-dimethyltetrathiafulvalene
 complex, and a theoretical study†
;
_journal_issue                   9
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              1546
_journal_paper_doi               10.1039/b103392c
_journal_year                    2001
_chemical_formula_moiety         'C18 H7 N5 O11,(C4 H8 O2)2'
_chemical_formula_sum            'C26 H23 N5 O15'
_chemical_formula_weight         645.49
_chemical_name_systematic
; 
9-(5-nitrofuran-2-ylidene)-2,4,5,7-tetranitrofluorene: dioxane (1:2) 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.43(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.588(5)
_cell_length_b                   8.667(3)
_cell_length_c                   21.798(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.3
_cell_measurement_theta_min      15.6
_cell_volume                     2777.2(14)
_computing_cell_refinement       AFC/MSC
_computing_data_collection       AFC/MSC
_computing_data_reduction        TEXSAN
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Rigaku AFC6S 4-circle diffractometer'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3426
_diffrn_reflns_theta_full        49.99
_diffrn_reflns_theta_max         49.99
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.120
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8493
_exptl_absorpt_process_details   'T_max,min from psi-scans'
_exptl_crystal_colour            amber
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00099(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0366
_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)+(0.0478P)²+1.2514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                2236
_reflns_number_total             2770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b103392c.txt
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7216984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_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
O1 O 0.59179(15) 0.3916(3) 0.50299(10) 0.0394(6) Uani 1 1 d . . .
O2 O 0.73832(16) 0.4063(2) 0.53394(9) 0.0363(6) Uani 1 1 d . . .
O3 O 0.90349(14) 0.4467(3) 0.76953(10) 0.0404(6) Uani 1 1 d . . .
O4 O 0.85174(13) 0.6525(3) 0.80236(10) 0.0346(6) Uani 1 1 d . . .
O5 O 0.80064(14) 0.3741(3) 0.85807(10) 0.0394(6) Uani 1 1 d . . .
O6 O 0.84648(14) 0.5587(3) 0.92939(10) 0.0472(7) Uani 1 1 d . . .
O7 O 0.57925(15) 0.6946(3) 0.99089(10) 0.0505(7) Uani 1 1 d . . .
O8 O 0.44664(17) 0.7017(3) 0.91700(10) 0.0505(7) Uani 1 1 d . . .
O9 O 0.30082(16) 0.8836(3) 0.81301(11) 0.0497(7) Uani 1 1 d . . .
O10 O 0.16623(18) 0.9421(3) 0.74617(12) 0.0556(7) Uani 1 1 d . . .
O11 O 0.34853(13) 0.7646(2) 0.71979(8) 0.0258(5) Uani 1 1 d . . .
N2 N 0.6660(2) 0.4186(3) 0.54399(11) 0.0288(7) Uani 1 1 d . . .
N4 N 0.84228(18) 0.5363(3) 0.76777(11) 0.0296(7) Uani 1 1 d . . .
N5 N 0.78888(18) 0.4953(3) 0.88354(12) 0.0329(7) Uani 1 1 d . . .
N7 N 0.5291(2) 0.6845(3) 0.93418(13) 0.0344(7) Uani 1 1 d . . .
N18 N 0.2426(2) 0.8855(3) 0.75899(14) 0.0367(7) Uani 1 1 d . . .
C1 C 0.5879(2) 0.5068(3) 0.61781(13) 0.0251(8) Uani 1 1 d . . .
H1 H 0.5323 0.5065 0.5823 0.030 Uiso 1 1 d R . .
C2 C 0.6678(2) 0.4660(3) 0.60920(13) 0.0245(8) Uani 1 1 d . . .
C3 C 0.7513(2) 0.4714(3) 0.65826(14) 0.0257(7) Uani 1 1 d . . .
H3 H 0.8060 0.4487 0.6499 0.031 Uiso 1 1 d R . .
C4 C 0.75204(19) 0.5116(3) 0.71968(13) 0.0229(8) Uani 1 1 d . . .
C5 C 0.69838(19) 0.5660(3) 0.85870(13) 0.0232(7) Uani 1 1 d . . .
C6 C 0.6606(2) 0.6066(3) 0.90516(14) 0.0261(8) Uani 1 1 d . . .
H6 H 0.6957 0.6056 0.9501 0.031 Uiso 1 1 d R . .
C7 C 0.5704(2) 0.6495(3) 0.88446(13) 0.0233(7) Uani 1 1 d . . .
C8 C 0.5169(2) 0.6538(3) 0.82014(13) 0.0239(7) Uani 1 1 d . . .
H8 H 0.4544 0.6812 0.8080 0.029 Uiso 1 1 d R . .
C9 C 0.51608(19) 0.6036(3) 0.70195(13) 0.0212(7) Uani 1 1 d . . .
C10 C 0.59016(19) 0.5481(3) 0.67995(13) 0.0220(7) Uani 1 1 d . . .
C11 C 0.6721(2) 0.5426(3) 0.73313(13) 0.0221(7) Uani 1 1 d . . .
C12 C 0.6499(2) 0.5757(3) 0.79232(13) 0.0221(7) Uani 1 1 d . . .
C13 C 0.55610(19) 0.6176(3) 0.77334(13) 0.0216(7) Uani 1 1 d . . .
C14 C 0.43261(19) 0.6348(3) 0.65833(13) 0.0247(8) Uani 1 1 d . . .
H14 H 0.4271 0.6040 0.6154 0.030 Uiso 1 1 d R . .
C15 C 0.3516(2) 0.7016(3) 0.66246(13) 0.0235(8) Uani 1 1 d . . .
C16 C 0.2681(2) 0.7171(3) 0.61564(14) 0.0269(8) Uani 1 1 d . . .
H16 H 0.2521 0.6836 0.5718 0.032 Uiso 1 1 d R . .
C17 C 0.2105(2) 0.7908(3) 0.64385(14) 0.0280(8) Uani 1 1 d . . .
H17 H 0.1483 0.8173 0.6236 0.034 Uiso 1 1 d R . .
C18 C 0.2626(2) 0.8161(3) 0.70609(14) 0.0252(8) Uani 1 1 d . . .
O21 O 0.55282(16) 0.9940(3) 0.87855(13) 0.0515(7) Uani 1 1 d . . .
C22 C 0.4895(2) 1.0673(4) 0.8235(2) 0.0530(10) Uani 1 1 d . . .
H221 H 0.4284 1.0667 0.8280 0.069 Uiso 1 1 d R . .
H222 H 0.4859 1.0092 0.7836 0.069 Uiso 1 1 d R . .
C23 C 0.5176(3) 1.2289(4) 0.81730(17) 0.0494(10) Uani 1 1 d . . .
H231 H 0.5772 1.2295 0.8103 0.064 Uiso 1 1 d R . .
H232 H 0.4723 1.2782 0.7792 0.064 Uiso 1 1 d R . .
O24 O 0.52328(15) 1.3141(3) 0.87465(11) 0.0474(6) Uani 1 1 d . . .
C25 C 0.5861(2) 1.2412(4) 0.92980(17) 0.0473(10) Uani 1 1 d . . .
H251 H 0.5884 1.2986 0.9696 0.062 Uiso 1 1 d R . .
H252 H 0.6476 1.2432 0.9260 0.062 Uiso 1 1 d R . .
C26 C 0.5589(3) 1.0803(4) 0.93585(18) 0.0514(10) Uani 1 1 d . . .
H261 H 0.6043 1.0311 0.9739 0.067 Uiso 1 1 d R . .
H262 H 0.4994 1.0791 0.9431 0.067 Uiso 1 1 d R . .
O31 O 0.6545(3) 0.7347(5) 0.4658(2) 0.0607(13) Uani 0.59 1 d P A 1
O31' O 0.5923(4) 0.7035(8) 0.4111(3) 0.0616(18) Uiso 0.41 1 d P A 2
C32 C 0.5678(3) 0.8205(4) 0.4390(2) 0.0618(11) Uani 1 1 d . . .
H321 H 0.5422 0.8386 0.4728 0.074 Uiso 0.59 1 d PR A 1
H322 H 0.5248 0.7626 0.4049 0.074 Uiso 0.59 1 d PR A 1
H323 H 0.5035 0.8140 0.4310 0.074 Uiso 0.41 1 d PR A 2
H324 H 0.5980 0.8174 0.4852 0.074 Uiso 0.41 1 d PR A 2
C33 C 0.5902(2) 0.9714(4) 0.4145(2) 0.0603(12) Uani 1 1 d . A .
H331 H 0.6293 1.0319 0.4496 0.072 Uiso 0.59 1 d PR B 1
H332 H 0.5349 1.0281 0.3951 0.072 Uiso 0.59 1 d PR B 1
H333 H 0.5586 1.0554 0.4262 0.072 Uiso 0.41 1 d PR B 2
H334 H 0.5747 0.9682 0.3681 0.072 Uiso 0.41 1 d PR B 2
O34 O 0.6369(3) 0.9429(4) 0.36224(16) 0.0408(10) Uani 0.59 1 d P A 1
O34' O 0.6876(4) 0.9841(7) 0.4456(3) 0.0527(16) Uiso 0.41 1 d P A 2
C35 C 0.7185(3) 0.8652(4) 0.3999(2) 0.0620(11) Uani 1 1 d . . .
H351 H 0.7522 0.9278 0.4363 0.074 Uiso 0.59 1 d PR A 1
H352 H 0.7557 0.8490 0.3731 0.074 Uiso 0.59 1 d PR A 1
H353 H 0.6838 0.8810 0.3549 0.074 Uiso 0.41 1 d PR A 2
H354 H 0.7821 0.8741 0.4057 0.074 Uiso 0.41 1 d PR A 2
C36 C 0.6960(3) 0.7124(4) 0.4233(2) 0.0593(11) Uani 1 1 d . A .
H361 H 0.6575 0.6534 0.3874 0.071 Uiso 0.59 1 d PR C 1
H362 H 0.7511 0.6554 0.4428 0.071 Uiso 0.59 1 d PR C 1
H363 H 0.7302 0.7012 0.4687 0.071 Uiso 0.41 1 d PR C 2
H364 H 0.7129 0.6302 0.4001 0.071 Uiso 0.41 1 d PR C 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C18 O11 C15 105.2(2)
O2 N2 O1 123.7(2)
O2 N2 C2 118.3(3)
O1 N2 C2 117.9(3)
O3 N4 O4 124.4(2)
O3 N4 C4 119.0(2)
O4 N4 C4 116.5(3)
O6 N5 O5 124.8(3)
O6 N5 C5 117.8(3)
O5 N5 C5 117.4(3)
O8 N7 O7 123.6(3)
O8 N7 C7 118.4(3)
O7 N7 C7 118.1(3)
O9 N18 O10 125.1(3)
O9 N18 C18 118.7(3)
O10 N18 C18 116.2(3)
C2 C1 C10 118.1(3)
C1 C2 C3 123.4(3)
C1 C2 N2 118.7(3)
C3 C2 N2 117.9(3)
C4 C3 C2 117.4(3)
C3 C4 C11 122.1(3)
C3 C4 N4 115.3(3)
C11 C4 N4 122.2(2)
C6 C5 C12 122.1(3)
C6 C5 N5 115.5(2)
C12 C5 N5 122.1(3)
C5 C6 C7 117.9(3)
C8 C7 C6 123.3(3)
C8 C7 N7 118.8(3)
C6 C7 N7 117.8(3)
C7 C8 C13 118.5(3)
C14 C9 C10 120.6(2)
C14 C9 C13 133.8(3)
C10 C9 C13 105.6(2)
C1 C10 C11 121.0(3)
C1 C10 C9 129.3(3)
C11 C10 C9 109.7(2)
C4 C11 C10 117.4(2)
C4 C11 C12 135.0(3)
C10 C11 C12 107.5(2)
C5 C12 C13 117.7(3)
C5 C12 C11 133.9(3)
C13 C12 C11 108.2(2)
C8 C13 C12 120.2(2)
C8 C13 C9 131.1(3)
C12 C13 C9 108.5(2)
C9 C14 C15 134.6(3)
C16 C15 O11 109.0(2)
C16 C15 C14 129.7(3)
O11 C15 C14 121.2(3)
C15 C16 C17 107.9(2)
C18 C17 C16 104.8(3)
O11 C18 C17 113.1(3)
O11 C18 N18 115.5(3)
C17 C18 N18 131.5(3)
C22 O21 C26 109.2(3)
O21 C22 C23 110.7(3)
O24 C23 C22 110.0(3)
C25 O24 C23 109.6(3)
O24 C25 C26 111.0(3)
O21 C26 C25 110.7(3)
C36 O31 C32 113.3(4)
C32 O31' C36 109.4(5)
O31' C32 O31 54.8(3)
O31' C32 C33 112.0(4)
O31 C32 C33 106.7(3)
O34' C33 C32 103.5(4)
O34' C33 O34 71.5(3)
C32 C33 O34 110.0(3)
C35 O34 C33 101.3(3)
C33 O34' C35 98.3(4)
O34 C35 C36 110.2(3)
O34 C35 O34' 70.3(3)
C36 C35 O34' 101.6(4)
O31 C36 C35 109.6(4)
O31 C36 O31' 52.9(3)
C35 C36 O31' 109.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.226(3)
O2 N2 1.223(3)
O3 N4 1.221(3)
O4 N4 1.237(3)
O5 N5 1.229(3)
O6 N5 1.229(3)
O7 N7 1.227(3)
O8 N7 1.222(3)
O9 N18 1.225(3)
O10 N18 1.230(3)
O11 C18 1.347(3)
O11 C15 1.379(3)
N2 C2 1.471(4)
N4 C4 1.464(4)
N5 C5 1.467(4)
N7 C7 1.465(4)
N18 C18 1.424(4)
C1 C2 1.367(4)
C1 C10 1.390(4)
C2 C3 1.384(4)
C3 C4 1.380(4)
C4 C11 1.398(4)
C5 C6 1.376(4)
C5 C12 1.394(4)
C6 C7 1.377(4)
C7 C8 1.373(4)
C8 C13 1.389(4)
C9 C14 1.359(4)
C9 C10 1.471(4)
C9 C13 1.476(4)
C10 C11 1.411(4)
C11 C12 1.471(4)
C12 C13 1.428(4)
C14 C15 1.419(4)
C15 C16 1.368(4)
C16 C17 1.400(4)
C17 C18 1.347(4)
O21 C22 1.425(4)
O21 C26 1.432(4)
C22 C23 1.487(5)
C23 O24 1.429(4)
O24 C25 1.421(4)
C25 C26 1.476(5)
O31 C36 1.309(5)
O31 C32 1.482(5)
O31' C32 1.304(7)
O31' C36 1.550(8)
C32 C33 1.497(5)
C33 O34' 1.446(7)
C33 O34 1.563(5)
O34 C35 1.432(5)
O34' C35 1.616(7)
C35 C36 1.502(5)
