#------------------------------------------------------------------------------
#$Date: 2019-11-10 00:47:21 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225454 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/52/4515288.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_4515288
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 H14 N4'
_chemical_formula_weight         406.43
_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                 103.5670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9996(7)
_cell_length_b                   10.0807(10)
_cell_length_c                   14.6724(15)
_cell_measurement_reflns_used    3151
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.47
_cell_volume                     1006.41(18)
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0150
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6108
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.474
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0344
_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          0.1195
_refine_ls_wR_factor_ref         0.1311
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1979
_reflns_number_total             2295
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am8b16848_si_004.cif
_cod_data_source_block           01_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4515288
_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   0.965
_shelx_estimated_absorpt_t_max   0.991
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
N1 N 0.08659(13) 0.93426(9) 0.40309(6) 0.0251(2) Uani 1 1 d . .
C1 C 0.20114(15) 0.81092(10) 0.62949(7) 0.0195(2) Uani 1 1 d . .
N002 N 0.27270(15) 0.84872(9) 0.70334(7) 0.0280(3) Uani 1 1 d . .
C2 C 0.11610(14) 0.76355(9) 0.53662(7) 0.0170(2) Uani 1 1 d . .
C3 C 0.09940(15) 0.85830(9) 0.46250(7) 0.0184(2) Uani 1 1 d . .
C4 C 0.05877(13) 0.63346(9) 0.51930(7) 0.0159(2) Uani 1 1 d . .
C5 C 0.07380(14) 0.53874(9) 0.59433(7) 0.0171(2) Uani 1 1 d . .
H5 H 0.1220 0.5657 0.6561 0.021 Uiso 1 1 calc R U
C8 C 0.58363(14) 0.65683(10) 0.56743(8) 0.0216(3) Uani 1 1 d . .
C7 C 0.61693(15) 0.78981(11) 0.54831(8) 0.0262(3) Uani 1 1 d . .
H7 H 0.6589 0.8490 0.5976 0.031 Uiso 1 1 calc R U
C6 C 0.01855(14) 0.41121(9) 0.57588(7) 0.0167(2) Uani 1 1 d . .
H6 H 0.0304 0.3513 0.6251 0.020 Uiso 1 1 calc R U
C9 C 0.51707(14) 0.56793(10) 0.49107(7) 0.0190(3) Uani 1 1 d . .
C10 C 0.48612(15) 0.61443(10) 0.39736(8) 0.0216(3) Uani 1 1 d . .
C11 C 0.52369(15) 0.74853(11) 0.38195(8) 0.0264(3) Uani 1 1 d . .
H11 H 0.5052 0.7800 0.3209 0.032 Uiso 1 1 calc R U
C12 C 0.58789(16) 0.83428(11) 0.45646(9) 0.0278(3) Uani 1 1 d . .
H12 H 0.6119 0.9227 0.4449 0.033 Uiso 1 1 calc R U
C13 C 0.42218(15) 0.52230(11) 0.32205(8) 0.0250(3) Uani 1 1 d . .
H13 H 0.4027 0.5517 0.2605 0.030 Uiso 1 1 calc R U
C14 C 0.38956(15) 0.39335(11) 0.33879(8) 0.0242(3) Uani 1 1 d . .
H14 H 0.3488 0.3358 0.2884 0.029 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'
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
N002 C1 C2 178.65(11) . .
C4 C2 C3 121.79(9) . .
C4 C2 C1 122.01(9) . .
C3 C2 C1 116.18(9) . .
N1 C3 C2 179.80(11) . .
C2 C4 C5 121.57(9) . .
C2 C4 C6 120.09(9) . 3_566
C5 C4 C6 118.34(9) . 3_566
C6 C5 C4 120.71(9) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C7 C8 C9 118.92(10) . .
C7 C8 C14 122.59(10) . 3_666
C9 C8 C14 118.48(9) . 3_666
C12 C7 C8 120.66(10) . .
C12 C7 H7 119.7 . .
C8 C7 H7 119.7 . .
C5 C6 C4 120.95(9) . 3_566
C5 C6 H6 119.5 . .
C4 C6 H6 119.5 3_566 .
C10 C9 C8 120.07(10) . .
C10 C9 C9 120.07(12) . 3_666
C8 C9 C9 119.86(12) . 3_666
C11 C10 C9 118.77(10) . .
C11 C10 C13 122.41(10) . .
C9 C10 C13 118.81(10) . .
C12 C11 C10 120.81(11) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C7 120.76(10) . .
C11 C12 H12 119.6 . .
C7 C12 H12 119.6 . .
C14 C13 C10 121.25(10) . .
C14 C13 H13 119.4 . .
C10 C13 H13 119.4 . .
C13 C14 C8 121.52(10) . 3_666
C13 C14 H14 119.2 . .
C8 C14 H14 119.2 3_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.1477(13) .
C1 N002 1.1470(14) .
C1 C2 1.4348(14) .
C2 C4 1.3776(13) .
C2 C3 1.4315(14) .
C4 C5 1.4423(13) .
C4 C6 1.4462(13) 3_566
C5 C6 1.3515(14) .
C5 H5 0.9300 .
C8 C7 1.4003(15) .
C8 C9 1.4249(14) .
C8 C14 1.4364(15) 3_666
C7 C12 1.3892(17) .
C7 H7 0.9300 .
C6 C4 1.4462(13) 3_566
C6 H6 0.9300 .
C9 C10 1.4204(15) .
C9 C9 1.425(2) 3_666
C10 C11 1.4056(15) .
C10 C13 1.4324(15) .
C11 C12 1.3834(16) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.3522(16) .
C13 H13 0.9300 .
C14 C8 1.4364(15) 3_666
C14 H14 0.9300 .
