#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:53:30 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180522 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/91/7219160.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_7219160
loop_
_publ_author_name
'Rudloff, Milan'
'Ackermann, Kai'
'Huth, Michael'
'Jeschke, Harald O.'
'Tomic, Milan'
'Valentí, Roser'
'Wolfram, Benedikt'
'Bröring, Martin'
'Bolte, Michael'
'Chercka, Dennis'
'Baumgarten, Martin'
'Müllen, Klaus'
_publ_section_title
;
 Charge transfer tuning by chemical substitution and uniaxial pressure in
 the organic complex tetramethoxypyrene-tetracyanoquinodimethane.
;
_journal_issue                   6
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              4118
_journal_page_last               4126
_journal_paper_doi               10.1039/c4cp04461d
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H18 O4, C12 F4 N4'
_chemical_formula_sum            'C32 H18 F4 N4 O4'
_chemical_formula_weight         598.50
_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
_audit_update_record
;
2014-05-08 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                61.373(13)
_cell_angle_beta                 71.958(14)
_cell_angle_gamma                84.063(14)
_cell_formula_units_Z            1
_cell_length_a                   6.8078(13)
_cell_length_b                   10.6592(18)
_cell_length_c                   10.840(2)
_cell_measurement_reflns_used    3415
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      3.3
_cell_volume                     655.6(2)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5551
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0551
_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)+(0.0693P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                1500
_reflns_number_total             2305
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4cp04461d1.cif
_cod_data_source_block           wa1460
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 7219160.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7219160
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
O1 O -0.1544(4) 0.3357(2) 0.9238(2) 0.0400(6) Uani 1 1 d .
O2 O 0.2199(3) 0.3668(2) 0.2083(2) 0.0334(5) Uani 1 1 d .
C1 C -0.0489(4) 0.3445(3) 0.6902(3) 0.0233(6) Uani 1 1 d .
C2 C 0.0091(4) 0.4249(3) 0.5340(3) 0.0218(6) Uani 1 1 d .
C3 C 0.0854(4) 0.3540(3) 0.4477(3) 0.0250(6) Uani 1 1 d .
C4 C 0.1010(5) 0.2053(3) 0.5178(3) 0.0295(7) Uani 1 1 d .
H4 H 0.1549 0.1571 0.4609 0.035 Uiso 1 1 calc R
C5 C 0.0384(5) 0.1290(3) 0.6690(3) 0.0315(7) Uani 1 1 d .
H5 H 0.0466 0.0280 0.7154 0.038 Uiso 1 1 calc R
C6 C -0.0365(5) 0.1965(3) 0.7551(3) 0.0282(7) Uani 1 1 d .
H6 H -0.0798 0.1412 0.8594 0.034 Uiso 1 1 calc R
C7 C -0.1216(4) 0.4189(3) 0.7766(3) 0.0259(6) Uani 1 1 d .
C8 C -0.3498(5) 0.3357(4) 1.0227(4) 0.0465(9) Uani 1 1 d .
H8A H -0.3519 0.4183 1.0396 0.070 Uiso 1 1 calc R
H8B H -0.3718 0.2473 1.1164 0.070 Uiso 1 1 calc R
H8C H -0.4600 0.3414 0.9799 0.070 Uiso 1 1 calc R
C9 C 0.1410(4) 0.4375(3) 0.2901(3) 0.0266(6) Uani 1 1 d .
C10 C 0.0673(6) 0.3168(4) 0.1744(4) 0.0466(9) Uani 1 1 d .
H10A H -0.0276 0.2455 0.2657 0.070 Uiso 1 1 calc R
H10B H 0.1352 0.2732 0.1114 0.070 Uiso 1 1 calc R
H10C H -0.0104 0.3974 0.1227 0.070 Uiso 1 1 calc R
C11 C 0.4247(4) 0.4621(3) 0.6469(3) 0.0242(6) Uani 1 1 d .
F11 F 0.3539(3) 0.42573(17) 0.78983(17) 0.0307(4) Uani 1 1 d .
C12 C 0.4410(4) 0.5999(3) 0.5492(3) 0.0225(6) Uani 1 1 d .
F12 F 0.3862(3) 0.69612(17) 0.59718(17) 0.0327(4) Uani 1 1 d .
C13 C 0.5168(4) 0.6510(3) 0.3922(3) 0.0232(6) Uani 1 1 d .
C14 C 0.5294(4) 0.7929(3) 0.2913(3) 0.0257(6) Uani 1 1 d .
C15 C 0.6153(5) 0.8446(3) 0.1355(3) 0.0334(7) Uani 1 1 d .
N15 N 0.6844(5) 0.8917(3) 0.0113(3) 0.0471(8) Uani 1 1 d .
C16 C 0.4653(5) 0.9065(3) 0.3291(3) 0.0317(7) Uani 1 1 d .
N16 N 0.4176(5) 1.0020(3) 0.3505(3) 0.0495(8) 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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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
C7 O1 C8 119.1(2) . .
C9 O2 C10 114.1(2) . .
C6 C1 C2 118.9(2) . .
C6 C1 C7 122.1(3) . .
C2 C1 C7 119.0(2) . .
C2 C2 C3 120.6(3) 2_566 .
C2 C2 C1 119.7(3) 2_566 .
C3 C2 C1 119.7(2) . .
C4 C3 C2 119.4(3) . .
C4 C3 C9 122.0(2) . .
C2 C3 C9 118.6(2) . .
C5 C4 C3 120.0(2) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C4 C5 C6 121.4(3) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 120.5(3) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
C9 C7 O1 124.4(2) 2_566 .
C9 C7 C1 120.6(2) 2_566 .
O1 C7 C1 114.9(2) . .
O1 C8 H8A 109.5 . .
O1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 O2 120.9(2) 2_566 .
C7 C9 C3 121.5(2) 2_566 .
O2 C9 C3 117.6(2) . .
O2 C10 H10A 109.5 . .
O2 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
O2 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C12 C11 F11 118.4(2) . .
C12 C11 C13 123.7(2) . 2_666
F11 C11 C13 117.9(2) . 2_666
C11 C12 F12 118.9(2) . .
C11 C12 C13 123.0(2) . .
F12 C12 C13 118.1(2) . .
C14 C13 C11 123.7(2) . 2_666
C14 C13 C12 123.0(2) . .
C11 C13 C12 113.3(2) 2_666 .
C13 C14 C15 123.1(2) . .
C13 C14 C16 124.1(2) . .
C15 C14 C16 112.8(2) . .
N15 C15 C14 176.8(3) . .
N16 C16 C14 176.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.359(3) .
O1 C8 1.427(4) .
O2 C9 1.380(3) .
O2 C10 1.427(4) .
C1 C6 1.392(4) .
C1 C2 1.422(4) .
C1 C7 1.447(3) .
C2 C2 1.416(5) 2_566
C2 C3 1.418(3) .
C3 C4 1.401(4) .
C3 C9 1.437(4) .
C4 C5 1.375(4) .
C4 H4 0.9500 .
C5 C6 1.386(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C9 1.356(4) 2_566
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C7 1.356(4) 2_566
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.328(4) .
C11 F11 1.336(3) .
C11 C13 1.441(4) 2_666
C12 F12 1.332(3) .
C12 C13 1.443(4) .
C13 C14 1.369(4) .
C13 C11 1.441(4) 2_666
C14 C15 1.436(4) .
C14 C16 1.442(4) .
C15 N15 1.138(4) .
C16 N16 1.144(4) .
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_4
C6 C1 C2 C2 177.8(3) . 2_566
C7 C1 C2 C2 -1.3(5) . 2_566
C6 C1 C2 C3 -2.4(4) . .
C7 C1 C2 C3 178.5(3) . .
C2 C2 C3 C4 -179.7(3) 2_566 .
C1 C2 C3 C4 0.5(4) . .
C2 C2 C3 C9 -0.8(5) 2_566 .
C1 C2 C3 C9 179.4(3) . .
C2 C3 C4 C5 1.4(4) . .
C9 C3 C4 C5 -177.4(3) . .
C3 C4 C5 C6 -1.5(5) . .
C4 C5 C6 C1 -0.5(5) . .
C2 C1 C6 C5 2.4(4) . .
C7 C1 C6 C5 -178.5(3) . .
C8 O1 C7 C9 57.0(4) . 2_566
C8 O1 C7 C1 -127.1(3) . .
C6 C1 C7 C9 -176.9(3) . 2_566
C2 C1 C7 C9 2.2(4) . 2_566
C6 C1 C7 O1 7.0(4) . .
C2 C1 C7 O1 -173.9(3) . .
C10 O2 C9 C7 -90.1(4) . 2_566
C10 O2 C9 C3 91.5(3) . .
C4 C3 C9 C7 178.8(3) . 2_566
C2 C3 C9 C7 -0.1(4) . 2_566
C4 C3 C9 O2 -2.8(4) . .
C2 C3 C9 O2 178.3(2) . .
F11 C11 C12 F12 -0.1(4) . .
C13 C11 C12 F12 -178.7(3) 2_666 .
F11 C11 C12 C13 179.6(3) . .
C13 C11 C12 C13 1.0(5) 2_666 .
C11 C12 C13 C14 178.5(3) . .
F12 C12 C13 C14 -1.8(4) . .
C11 C12 C13 C11 -0.9(4) . 2_666
F12 C12 C13 C11 178.8(3) . 2_666
C11 C13 C14 C15 -4.2(5) 2_666 .
C12 C13 C14 C15 176.5(3) . .
C11 C13 C14 C16 178.0(3) 2_666 .
C12 C13 C14 C16 -1.3(5) . .
