#------------------------------------------------------------------------------
#$Date: 2019-11-10 00:47:39 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225455 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/52/4515289.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_4515289
loop_
_publ_author_name
'Yang, Yuying'
'Liu, Guangfeng'
'Liu, Jie'
'Wei, Mengmeng'
'Wang, Zhongxuan'
'Hao, Xiaotao'
'Maheswar Repaka, D. V.'
'Ramanujan, Raju V.'
'Tao, Xutang'
'Qin, Wei'
'Zhang, Qichun'
_publ_section_title
;
 Anisotropic Magnetoelectric Coupling and Cotton-Mouton Effects in the
 Organic Magnetic Charge-Transfer Complex Pyrene-F₄TCNQ.
;
_journal_issue                   51
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              44654
_journal_page_last               44659
_journal_paper_doi               10.1021/acsami.8b16848
_journal_volume                  10
_journal_year                    2018
_chemical_formula_sum            'C28 H10 F4 N4'
_chemical_formula_weight         478.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.983(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5612(15)
_cell_length_b                   18.654(4)
_cell_length_c                   8.5145(19)
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.18
_cell_volume                     1026.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5114
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_min         2.184
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.195
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1827
_reflns_number_total             2316
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am8b16848_si_002.cif
_cod_data_source_block           liujie201687_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4515289
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 0.42124(12) 0.50127(4) 0.17537(8) 0.0153(2) Uani 1 1 d . .
N1 N 0.47075(19) 0.24144(6) 0.45859(15) 0.0216(3) Uani 1 1 d . .
C1 C 0.4338(2) 0.36167(7) 0.16279(16) 0.0147(3) Uani 1 1 d . .
C2 C 0.46097(19) 0.36772(7) 0.33355(15) 0.0123(3) Uani 1 1 d . .
F2 F 0.45817(12) 0.62433(4) 0.33030(9) 0.0156(2) Uani 1 1 d . .
N2 N 0.41648(18) 0.35046(6) 0.02839(14) 0.0207(3) Uani 1 1 d . .
C3 C 0.4695(2) 0.29871(7) 0.41023(16) 0.0156(3) Uani 1 1 d . .
C4 C 0.47958(18) 0.43199(7) 0.41493(15) 0.0112(3) Uani 1 1 d . .
C5 C 0.4617(2) 0.50054(6) 0.33479(15) 0.0112(3) Uani 1 1 d . .
C6 C 0.48062(19) 0.56352(7) 0.41375(15) 0.0116(3) Uani 1 1 d . .
C8 C 0.9360(2) 0.58941(7) 0.26949(16) 0.0163(3) Uani 1 1 d . .
H8 H 0.9179 0.6301 0.2054 0.020 Uiso 1 1 calc R U
C7 C 0.9173(2) 0.52377(8) 0.20066(15) 0.0161(3) Uani 1 1 d . .
H7 H 0.8849 0.5203 0.0902 0.019 Uiso 1 1 calc R U
C9 C 0.98322(19) 0.59743(7) 0.43927(16) 0.0129(3) Uani 1 1 d . .
C10 C 1.00897(19) 0.53455(7) 0.53665(15) 0.0108(3) Uani 1 1 d . .
C11 C 1.05366(19) 0.54086(7) 0.70538(15) 0.0127(3) Uani 1 1 d . .
C12 C 1.0689(2) 0.60950(7) 0.77415(17) 0.0171(3) Uani 1 1 d . .
H12 H 1.0962 0.6143 0.8845 0.020 Uiso 1 1 calc R U
C13 C 1.0437(2) 0.67021(7) 0.67869(18) 0.0195(3) Uani 1 1 d . .
H13 H 1.0550 0.7153 0.7260 0.023 Uiso 1 1 calc R U
C14 C 1.00191(19) 0.66470(7) 0.51369(18) 0.0178(3) Uani 1 1 d . .
H14 H 0.9861 0.7061 0.4519 0.021 Uiso 1 1 calc R U
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'
N N 0.0061 0.0033 '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'
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
N2 C1 C2 173.87(13) . .
C4 C2 C1 124.10(11) . .
C4 C2 C3 123.78(12) . .
C1 C2 C3 112.12(11) . .
N1 C3 C2 174.19(15) . .
C2 C4 C5 122.63(12) . .
C2 C4 C6 122.98(12) . 3_666
C5 C4 C6 114.40(11) . 3_666
F1 C5 C6 118.82(11) . .
F1 C5 C4 118.30(11) . .
C6 C5 C4 122.87(13) . .
F2 C6 C5 118.91(12) . .
F2 C6 C4 118.34(11) . 3_666
C5 C6 C4 122.74(12) . 3_666
C7 C8 C9 121.24(12) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
C8 C7 C11 121.53(12) . 3_766
C8 C7 H7 119.2 . .
C11 C7 H7 119.2 3_766 .
C14 C9 C10 118.70(12) . .
C14 C9 C8 122.43(12) . .
C10 C9 C8 118.87(12) . .
C10 C10 C11 120.24(15) 3_766 .
C10 C10 C9 119.65(15) 3_766 .
C11 C10 C9 120.11(12) . .
C12 C11 C10 118.98(12) . .
C12 C11 C7 122.57(12) . 3_766
C10 C11 C7 118.45(12) . 3_766
C13 C12 C11 120.50(13) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C14 C13 C12 121.02(12) . .
C14 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C13 C14 C9 120.69(12) . .
C13 C14 H14 119.7 . .
C9 C14 H14 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.3372(14) .
N1 C3 1.1444(19) .
C1 N2 1.1494(18) .
C1 C2 1.4382(18) .
C2 C4 1.3796(18) .
C2 C3 1.4401(19) .
F2 C6 1.3330(14) .
C4 C5 1.4445(18) .
C4 C6 1.4391(18) 3_666
C5 C6 1.3487(18) .
C6 C4 1.4391(18) 3_666
C8 C7 1.354(2) .
C8 C9 1.4328(19) .
C8 H8 0.9300 .
C7 C11 1.4411(19) 3_766
C7 H7 0.9300 .
C9 C14 1.4016(19) .
C9 C10 1.4293(19) .
C10 C10 1.428(2) 3_766
C10 C11 1.4205(19) .
C11 C12 1.4042(18) .
C11 C7 1.4411(19) 3_766
C12 C13 1.387(2) .
C12 H12 0.9300 .
C13 C14 1.388(2) .
C13 H13 0.9300 .
C14 H14 0.9300 .
