#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:01:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180368 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/37/7203759.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_7203759
loop_
_publ_author_name
'Sévignon, Marc'
'Macaud, Mathieu'
'Favre-Réguillon, Alain'
'Schulz, Jürgen'
'Rocault, Muriel'
'Faure, René'
'Vrinat, Michel'
'Lemaire, Marc'
_publ_section_title
;
 Ultra-deep desulfurization of transportation fuels via charge-transfer
 complexes under ambient conditions
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              413
_journal_paper_doi               10.1039/b502672e
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C15 H4 N4 O5'
_chemical_formula_weight         320.22
_chemical_name_common            4,5-dicyano-2,7-dinitrofluorenone
_chemical_name_systematic
;
?
;
_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                 110.614(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1690(8)
_cell_length_b                   6.4510(4)
_cell_length_c                   15.2380(11)
_cell_measurement_reflns_used    8294
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1303.64(15)
_computing_cell_refinement       KappaCCD
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo, Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXTL v 5.03'
_computing_structure_solution    'SHELXTL v 5.03'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.838
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       KappaCCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5902
_diffrn_reflns_theta_full        27.69
_diffrn_reflns_theta_max         27.69
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Multiscan, sortav blessing (1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0772P)²+0.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                1680
_reflns_number_total             2562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b502672e.txt
_cod_data_source_block           compound_4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1303.64(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7203759
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
C1 C 0.82423(17) 0.1210(3) 0.00116(15) 0.0470(6) Uani 1 1 d . . .
H1 H 0.8628 0.0294 -0.0166 0.049(6) Uiso 1 1 d R . .
C2 C 0.72213(17) 0.0969(3) -0.02220(16) 0.0482(6) Uani 1 1 d . . .
C3 C 0.66353(17) 0.2377(4) 0.00273(16) 0.0506(6) Uani 1 1 d . . .
H3 H 0.5920 0.2183 -0.0152 0.050 Uiso 1 1 d R . .
C4 C 0.70777(16) 0.4109(4) 0.05491(15) 0.0456(5) Uani 1 1 d . . .
C4A C 0.81156(15) 0.4407(3) 0.08165(14) 0.0397(5) Uani 1 1 d . . .
C4B C 0.88321(14) 0.6044(3) 0.13413(14) 0.0379(5) Uani 1 1 d . . .
C5 C 0.87455(15) 0.7814(3) 0.18223(14) 0.0411(5) Uani 1 1 d . . .
C6 C 0.95909(17) 0.9092(3) 0.22026(16) 0.0458(5) Uani 1 1 d . . .
H6 H 0.9550 1.0327 0.2539 0.050 Uiso 1 1 d R . .
C7 C 1.04927(16) 0.8599(3) 0.21071(15) 0.0458(5) Uani 1 1 d . . .
C8 C 1.06200(16) 0.6811(4) 0.16816(15) 0.0458(5) Uani 1 1 d . . .
H8 H 1.1273 0.6494 0.1660 0.050 Uiso 1 1 d R . .
C8A C 0.97911(15) 0.5573(3) 0.13106(15) 0.0413(5) Uani 1 1 d . . .
C9 C 0.97380(16) 0.3593(3) 0.08141(15) 0.0449(5) Uani 1 1 d . . .
C9A C 0.86685(15) 0.2926(3) 0.05206(15) 0.0411(5) Uani 1 1 d . . .
C10 C 0.63854(18) 0.5519(4) 0.0735(2) 0.0652(8) Uani 1 1 d . . .
C11 C 0.78622(17) 0.8486(4) 0.19904(17) 0.0517(6) Uani 1 1 d . . .
N1 N 0.67167(18) -0.0825(3) -0.07650(15) 0.0637(6) Uani 1 1 d . . .
N2 N 0.57667(18) 0.6512(5) 0.0822(2) 0.1118(13) Uani 1 1 d . . .
N3 N 0.72158(18) 0.9173(4) 0.21731(19) 0.0828(8) Uani 1 1 d . . .
N4 N 1.13444(16) 1.0025(4) 0.24930(15) 0.0576(6) Uani 1 1 d . . .
O1 O 1.04235(12) 0.2702(3) 0.06702(13) 0.0609(5) Uani 1 1 d . . .
O2 O 0.72423(17) -0.2256(3) -0.08253(16) 0.0848(7) Uani 1 1 d . . .
O3 O 0.58015(17) -0.0784(4) -0.11268(18) 0.0991(8) Uani 1 1 d . . .
O4 O 1.12292(16) 1.1523(4) 0.29263(16) 0.0840(7) Uani 1 1 d . . .
O5 O 1.21123(14) 0.9641(3) 0.23362(16) 0.0785(6) 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 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C9A C1 C2 117.0(2) . . ?
C9A C1 H1 120.3 . . ?
C2 C1 H1 122.6 . . ?
C3 C2 C1 122.6(2) . . ?
C3 C2 N1 117.4(2) . . ?
C1 C2 N1 120.0(2) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C4A 119.7(2) . . ?
C3 C4 C10 114.9(2) . . ?
C4A C4 C10 125.3(2) . . ?
C4 C4A C9A 117.51(19) . . ?
C4 C4A C4B 134.82(19) . . ?
C9A C4A C4B 107.62(18) . . ?
C5 C4B C8A 117.46(19) . . ?
C5 C4B C4A 134.32(18) . . ?
C8A C4B C4A 108.23(17) . . ?
C4B C5 C6 118.81(19) . . ?
C4B C5 C11 126.2(2) . . ?
C6 C5 C11 115.0(2) . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 N4 119.5(2) . . ?
C6 C7 N4 118.5(2) . . ?
C7 C8 C8A 116.9(2) . . ?
C7 C8 H8 119.1 . . ?
C8A C8 H8 124.0 . . ?
C8 C8A C4B 124.0(2) . . ?
C8 C8A C9 126.87(19) . . ?
C4B C8A C9 109.17(18) . . ?
O1 C9 C8A 127.2(2) . . ?
O1 C9 C9A 127.2(2) . . ?
C8A C9 C9A 105.57(17) . . ?
C1 C9A C4A 123.25(19) . . ?
C1 C9A C9 127.37(19) . . ?
C4A C9A C9 109.33(19) . . ?
N2 C10 C4 173.2(3) . . ?
N3 C11 C5 173.3(3) . . ?
O2 N1 O3 124.6(2) . . ?
O2 N1 C2 117.2(2) . . ?
O3 N1 C2 118.1(2) . . ?
O4 N4 O5 124.7(2) . . ?
O4 N4 C7 117.9(2) . . ?
O5 N4 C7 117.3(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9A 1.364(3) . ?
C1 C2 1.371(3) . ?
C1 H1 0.9081 . ?
C2 C3 1.371(3) . ?
C2 N1 1.456(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9601 . ?
C4 C4A 1.394(3) . ?
C4 C10 1.437(3) . ?
C4A C9A 1.407(3) . ?
C4A C4B 1.488(3) . ?
C4B C5 1.386(3) . ?
C4B C8A 1.409(3) . ?
C5 C6 1.401(3) . ?
C5 C11 1.430(3) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9600 . ?
C7 C8 1.366(3) . ?
C7 N4 1.466(3) . ?
C8 C8A 1.367(3) . ?
C8 H8 0.9601 . ?
C8A C9 1.473(3) . ?
C9 O1 1.213(3) . ?
C9 C9A 1.485(3) . ?
C10 N2 1.131(3) . ?
C11 N3 1.137(3) . ?
N1 O2 1.210(3) . ?
N1 O3 1.218(3) . ?
N4 O4 1.213(3) . ?
N4 O5 1.219(3) . ?
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
_geom_torsion_publ_flag
C9A C1 C2 C3 0.6(3) . . . . ?
C9A C1 C2 N1 180.0(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
N1 C2 C3 C4 179.6(2) . . . . ?
C2 C3 C4 C4A 0.0(3) . . . . ?
C2 C3 C4 C10 177.4(2) . . . . ?
C3 C4 C4A C9A 1.3(3) . . . . ?
C10 C4 C4A C9A -175.9(2) . . . . ?
C3 C4 C4A C4B 178.4(2) . . . . ?
C10 C4 C4A C4B 1.2(4) . . . . ?
C4 C4A C4B C5 5.8(4) . . . . ?
C9A C4A C4B C5 -176.9(2) . . . . ?
C4 C4A C4B C8A -174.3(2) . . . . ?
C9A C4A C4B C8A 2.9(2) . . . . ?
C8A C4B C5 C6 3.6(3) . . . . ?
C4A C4B C5 C6 -176.6(2) . . . . ?
C8A C4B C5 C11 -175.4(2) . . . . ?
C4A C4B C5 C11 4.4(4) . . . . ?
C4B C5 C6 C7 -0.4(3) . . . . ?
C11 C5 C6 C7 178.7(2) . . . . ?
C5 C6 C7 C8 -3.2(3) . . . . ?
C5 C6 C7 N4 178.1(2) . . . . ?
C6 C7 C8 C8A 3.2(3) . . . . ?
N4 C7 C8 C8A -178.11(19) . . . . ?
C7 C8 C8A C4B 0.3(3) . . . . ?
C7 C8 C8A C9 179.4(2) . . . . ?
C5 C4B C8A C8 -3.6(3) . . . . ?
C4A C4B C8A C8 176.5(2) . . . . ?
C5 C4B C8A C9 177.08(19) . . . . ?
C4A C4B C8A C9 -2.8(2) . . . . ?
C8 C8A C9 O1 2.0(4) . . . . ?
C4B C8A C9 O1 -178.8(2) . . . . ?
C8 C8A C9 C9A -177.6(2) . . . . ?
C4B C8A C9 C9A 1.6(2) . . . . ?
C2 C1 C9A C4A 0.8(3) . . . . ?
C2 C1 C9A C9 -176.4(2) . . . . ?
C4 C4A C9A C1 -1.7(3) . . . . ?
C4B C4A C9A C1 -179.5(2) . . . . ?
C4 C4A C9A C9 175.90(18) . . . . ?
C4B C4A C9A C9 -1.9(2) . . . . ?
O1 C9 C9A C1 -1.8(4) . . . . ?
C8A C9 C9A C1 177.7(2) . . . . ?
O1 C9 C9A C4A -179.3(2) . . . . ?
C8A C9 C9A C4A 0.3(2) . . . . ?
C3 C4 C10 N2 -8(3) . . . . ?
C4A C4 C10 N2 170(3) . . . . ?
C4B C5 C11 N3 177(2) . . . . ?
C6 C5 C11 N3 -2(3) . . . . ?
C3 C2 N1 O2 -165.6(2) . . . . ?
C1 C2 N1 O2 15.0(3) . . . . ?
C3 C2 N1 O3 14.5(4) . . . . ?
C1 C2 N1 O3 -164.8(2) . . . . ?
C8 C7 N4 O4 -174.7(2) . . . . ?
C6 C7 N4 O4 4.0(3) . . . . ?
C8 C7 N4 O5 6.9(3) . . . . ?
C6 C7 N4 O5 -174.4(2) . . . . ?
