#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:05:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180489 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/58/7215815.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_7215815
loop_
_publ_author_name
'Sutton, Ashley L.'
'Abrahams, Brendan F.'
'D'Alessandro, Deanna M.'
'Elliott, Robert W.'
'Hudson, Timothy A.'
'Robson, Richard'
'Usov, Pavel M.'
_publ_section_title
;
 Structural and optical investigations of charge transfer complexes
 involving the F4TCNQ dianion
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/c4ce00289j
_journal_year                    2014
_chemical_formula_sum            'C24 H15 F2 N4 O2'
_chemical_formula_weight         429.40
_chemical_name_systematic
;
 ?
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.300(4)
_cell_angle_beta                 98.584(4)
_cell_angle_gamma                116.492(5)
_cell_formula_units_Z            2
_cell_length_a                   8.1317(4)
_cell_length_b                   9.0430(5)
_cell_length_c                   15.1631(7)
_cell_measurement_reflns_used    4456
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      73.7130
_cell_measurement_theta_min      3.0052
_cell_volume                     966.98(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6526
_diffrn_reflns_theta_full        73.88
_diffrn_reflns_theta_max         73.88
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'large shard'
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.6724
_exptl_crystal_size_mid          0.3612
_exptl_crystal_size_min          0.1971
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0336
_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)+(0.0430P)²+0.3568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                3493
_reflns_number_total             3770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00289j2.cif
_cod_data_source_block           12F4TCNQ
_cod_original_cell_volume        966.98(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7215815
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.77107(10) 0.61651(10) 0.40478(5) 0.02454(17) Uani 1 1 d .
F2 F 0.13062(10) 0.31386(9) 0.41978(5) 0.02425(17) Uani 1 1 d .
O1 O 1.59001(13) 0.87854(12) -0.13849(6) 0.0273(2) Uani 1 1 d .
O2 O 1.72453(14) 0.79503(15) -0.03620(7) 0.0359(3) Uani 1 1 d .
C24 C 0.44422(16) 0.46175(14) 0.39963(8) 0.0173(2) Uani 1 1 d .
N2 N 1.04857(14) 0.72623(13) 0.21063(7) 0.0197(2) Uani 1 1 d .
C23 C 0.62974(16) 0.55755(15) 0.44954(8) 0.0184(2) Uani 1 1 d .
C28 C 0.20254(17) 0.31272(15) 0.25336(8) 0.0200(2) Uani 1 1 d .
N1 N 1.59367(15) 0.81795(14) -0.07024(7) 0.0227(2) Uani 1 1 d .
C4 C 1.14305(17) 0.77069(15) -0.01591(8) 0.0204(2) Uani 1 1 d .
H4 H 1.0419 0.7915 -0.0392 0.024 Uiso 1 1 calc R
N3 N 0.62075(16) 0.54071(15) 0.19716(7) 0.0267(2) Uani 1 1 d .
C25 C 0.31771(16) 0.40633(15) 0.45681(8) 0.0180(2) Uani 1 1 d .
C12 C 1.24267(17) 0.88387(15) 0.49816(8) 0.0207(2) Uani 1 1 d .
C27 C 0.51926(17) 0.48875(15) 0.24520(8) 0.0204(2) Uani 1 1 d .
C1 C 1.43787(18) 0.70698(17) 0.05223(8) 0.0237(3) Uani 1 1 d .
H1 H 1.5384 0.6848 0.0747 0.028 Uiso 1 1 calc R
C6 C 1.43395(17) 0.77381(15) -0.02553(8) 0.0197(2) Uani 1 1 d .
C8 C 1.16859(19) 0.94084(16) 0.34217(9) 0.0243(3) Uani 1 1 d .
H8 H 1.2069 1.0546 0.3686 0.029 Uiso 1 1 calc R
C22 C 0.98267(17) 0.67201(16) 0.11057(8) 0.0222(3) Uani 1 1 d .
H22A H 0.9139 0.7320 0.0878 0.027 Uiso 1 1 calc R
H22B H 0.8939 0.5497 0.0952 0.027 Uiso 1 1 calc R
C5 C 1.28787(17) 0.80391(15) -0.06147(8) 0.0207(2) Uani 1 1 d .
H5 H 1.2866 0.8463 -0.1160 0.025 Uiso 1 1 calc R
C26 C 0.38943(17) 0.42287(15) 0.30064(8) 0.0191(2) Uani 1 1 d .
N4 N 0.04951(16) 0.22302(15) 0.21301(7) 0.0268(2) Uani 1 1 d .
C11 C 1.05268(17) 0.61503(16) 0.26214(8) 0.0218(3) Uani 1 1 d .
H11 H 1.0103 0.5013 0.2340 0.026 Uiso 1 1 calc R
C10 C 1.11736(17) 0.66428(16) 0.35468(8) 0.0215(3) Uani 1 1 d .
H10 H 1.1211 0.5846 0.3898 0.026 Uiso 1 1 calc R
C3 C 1.14455(17) 0.70726(15) 0.06362(8) 0.0194(2) Uani 1 1 d .
C2 C 1.29094(18) 0.67326(17) 0.09638(8) 0.0239(3) Uani 1 1 d .
H2 H 1.2902 0.6265 0.1495 0.029 Uiso 1 1 calc R
C9 C 1.17802(16) 0.83057(15) 0.39818(8) 0.0201(2) Uani 1 1 d .
C7 C 1.10476(18) 0.88710(16) 0.24956(9) 0.0238(3) Uani 1 1 d .
H7 H 1.1002 0.9641 0.2126 0.029 Uiso 1 1 calc R
C13 C 1.23241(19) 1.02051(16) 0.54455(9) 0.0248(3) Uani 1 1 d .
H13 H 1.1872 1.0832 0.5113 0.030 Uiso 1 1 calc R
C15 C 1.3533(2) 0.97552(18) 0.68798(9) 0.0285(3) Uani 1 1 d .
H15 H 1.3897 1.0060 0.7525 0.034 Uiso 1 1 calc R
C14 C 1.2876(2) 1.06570(17) 0.63872(9) 0.0278(3) Uani 1 1 d .
H14 H 1.2802 1.1591 0.6695 0.033 Uiso 1 1 calc R
C16 C 1.3656(2) 0.84070(19) 0.64278(10) 0.0333(3) Uani 1 1 d .
H16 H 1.4112 0.7786 0.6763 0.040 Uiso 1 1 calc R
C17 C 1.3117(2) 0.79591(18) 0.54863(9) 0.0294(3) Uani 1 1 d .
H17 H 1.3220 0.7039 0.5181 0.035 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_1
_geom_angle_site_symmetry_3
C23 C24 C25 111.44(10) . .
C23 C24 C26 124.25(11) . .
C25 C24 C26 124.31(11) . .
C7 N2 C11 120.43(11) . .
C7 N2 C22 119.53(10) . .
C11 N2 C22 120.04(10) . .
F1 C23 C25 116.32(10) . 2_666
F1 C23 C24 119.22(10) . .
C25 C23 C24 124.43(11) 2_666 .
N4 C28 C26 178.76(13) . .
O2 N1 O1 123.60(11) . .
O2 N1 C6 118.15(10) . .
O1 N1 C6 118.24(10) . .
C5 C4 C3 120.66(11) . .
F2 C25 C23 116.43(10) . 2_666
F2 C25 C24 119.43(10) . .
C23 C25 C24 124.13(11) 2_666 .
C17 C12 C13 118.34(12) . .
C17 C12 C9 120.47(11) . .
C13 C12 C9 121.17(11) . .
N3 C27 C26 177.68(13) . .
C6 C1 C2 118.20(11) . .
C5 C6 C1 122.51(11) . .
C5 C6 N1 118.85(11) . .
C1 C6 N1 118.63(11) . .
C7 C8 C9 120.98(12) . .
N2 C22 C3 111.96(10) . .
C6 C5 C4 118.40(11) . .
C28 C26 C27 115.18(10) . .
C28 C26 C24 122.02(11) . .
C27 C26 C24 122.79(11) . .
N2 C11 C10 120.72(11) . .
C11 C10 C9 120.87(11) . .
C4 C3 C2 119.43(11) . .
C4 C3 C22 118.70(11) . .
C2 C3 C22 121.85(11) . .
C1 C2 C3 120.75(11) . .
C8 C9 C10 116.41(11) . .
C8 C9 C12 122.21(11) . .
C10 C9 C12 121.35(11) . .
N2 C7 C8 120.58(11) . .
C14 C13 C12 120.60(12) . .
C14 C15 C16 119.62(12) . .
C15 C14 C13 120.36(12) . .
C15 C16 C17 120.15(13) . .
C16 C17 C12 120.93(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C23 1.3533(13) .
F2 C25 1.3550(14) .
O1 N1 1.2256(14) .
O2 N1 1.2239(14) .
C24 C23 1.3958(17) .
C24 C25 1.4010(16) .
C24 C26 1.4561(16) .
N2 C7 1.3460(17) .
N2 C11 1.3479(16) .
N2 C22 1.4796(15) .
C23 C25 1.3777(17) 2_666
C28 N4 1.1593(17) .
C28 C26 1.4083(17) .
N1 C6 1.4716(15) .
C4 C5 1.3883(17) .
C4 C3 1.3918(17) .
N3 C27 1.1581(17) .
C25 C23 1.3777(17) 2_666
C12 C17 1.3918(18) .
C12 C13 1.3955(18) .
C12 C9 1.4774(17) .
C27 C26 1.4107(17) .
C1 C6 1.3851(17) .
C1 C2 1.3882(18) .
C6 C5 1.3820(17) .
C8 C7 1.3729(18) .
C8 C9 1.3987(17) .
C22 C3 1.5153(16) .
C11 C10 1.3702(17) .
C10 C9 1.4011(18) .
C3 C2 1.3936(17) .
C13 C14 1.3872(18) .
C15 C14 1.3826(19) .
C15 C16 1.383(2) .
C16 C17 1.3864(19) .
