#------------------------------------------------------------------------------
#$Date: 2017-11-07 03:05:58 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202769 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/72/1547293.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_1547293
loop_
_publ_author_name
'Margulies, Eric A.'
'Kerisit, Nicolas'
'Gawel, Przemyslaw'
'Mauck, Catherine M.'
'Ma, Lin'
'Miller, Claire E.'
'Young, Ryan M.'
'Trapp, Nils'
'Wu, Yi-Lin'
'Diederich, François'
'Wasielewski, Michael R.'
_publ_section_title
;
 Substituent Effects on Singlet Exciton Fission in Polycrystalline Thin
 Films of Cyano-Substituted Diaryltetracenes
;
_journal_issue                   39
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              21262
_journal_paper_doi               10.1021/acs.jpcc.7b07870
_journal_volume                  121
_journal_year                    2017
_chemical_formula_moiety         'C32 H14 F4 N2'
_chemical_formula_sum            'C32 H14 F4 N2'
_chemical_formula_weight         502.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_date             2015-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                102.679(5)
_cell_angle_beta                 92.770(5)
_cell_angle_gamma                103.071(5)
_cell_formula_units_Z            1
_cell_length_a                   7.0204(11)
_cell_length_b                   7.3076(13)
_cell_length_c                   11.485(2)
_cell_measurement_reflns_used    3643
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.95
_cell_volume                     556.96(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.586
_diffrn_reflns_theta_min         2.945
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0580 before and 0.0396 after correction.
The Ratio of minimum to maximum transmission is 0.9117.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0474P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2170
_reflns_number_total             2575
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp7b07870_si_002.cif
_cod_data_source_block           d040415_1_1_0m
_cod_depositor_comments
'Adding full bibliography for 1547291--1547294.cif.'
_cod_original_cell_volume        556.97(17)
_cod_database_code               1547293
_shelxl_version_number           2014/6
_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_max   0.993
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C13(H13), C14(H14)
;
_olex2_date_sample_data_collection 2015-04-09
_olex2_date_sample_submission    2015-04-09
_olex2_submission_original_sample_id d040415_1_1
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F1 F 0.75593(15) 0.15696(14) 0.36731(7) 0.0384(3) Uani 1 1 d .
F2 F 0.15915(10) 0.12924(11) 1.09767(7) 0.0212(2) Uani 1 1 d .
N1 N 1.24229(15) 0.36604(16) 0.66676(9) 0.0181(2) Uani 1 1 d .
C1 C 0.7688(2) 0.2006(2) 0.48937(11) 0.0237(3) Uani 1 1 d .
C2 C 0.77635(19) 0.3879(2) 0.54792(12) 0.0209(3) Uani 1 1 d .
H2 H 0.7696 0.4836 0.5048 0.025 Uiso 1 1 calc R
C3 C 0.79424(17) 0.43213(18) 0.67243(11) 0.0159(3) Uani 1 1 d .
H3 H 0.8013 0.5607 0.7154 0.019 Uiso 1 1 calc R
C4 C 0.80200(16) 0.29090(17) 0.73519(10) 0.0128(2) Uani 1 1 d .
C5 C 0.81932(17) 0.34494(16) 0.86895(10) 0.0120(2) Uani 1 1 d .
C6 C 0.99683(16) 0.46362(16) 0.93569(10) 0.0110(2) Uani 1 1 d .
C7 C 0.7731(2) 0.0556(2) 0.54712(12) 0.0231(3) Uani 1 1 d .
H7 H 0.7656 -0.0726 0.5032 0.028 Uiso 1 1 calc R
C8 C 0.78893(18) 0.10171(18) 0.67130(11) 0.0181(3) Uani 1 1 d .
H8 H 0.7909 0.0037 0.7134 0.022 Uiso 1 1 calc R
C9 C 0.65362(17) 0.28737(16) 0.92705(10) 0.0118(2) Uani 1 1 d .
C10 C 0.65715(17) 0.35711(16) 1.05426(10) 0.0119(2) Uani 1 1 d .
C11 C 0.48473(17) 0.30088(17) 1.11123(11) 0.0140(2) Uani 1 1 d .
H11 H 0.4840 0.3452 1.1954 0.017 Uiso 1 1 calc R
C12 C 0.32262(17) 0.18355(17) 1.04333(11) 0.0149(3) Uani 1 1 d .
C13 C 0.31181(17) 0.11420(17) 0.91799(11) 0.0154(3) Uani 1 1 d .
H13 H 0.1936 0.0328 0.8739 0.018 Uiso 1 1 calc R
C14 C 0.47350(17) 0.16613(17) 0.86173(11) 0.0142(3) Uani 1 1 d .
H14 H 0.4675 0.1213 0.7772 0.017 Uiso 1 1 calc R
C15 C 1.17210(16) 0.51500(16) 0.88079(10) 0.0115(2) Uani 1 1 d .
C16 C 1.19564(17) 0.42796(17) 0.75871(11) 0.0132(2) 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'
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
F1 C1 C2 117.99(13) . .
F1 C1 C7 118.37(12) . .
C7 C1 C2 123.64(12) . .
C1 C2 H2 121.2 . .
C1 C2 C3 117.58(13) . .
C3 C2 H2 121.2 . .
C2 C3 H3 119.5 . .
C2 C3 C4 120.98(12) . .
C4 C3 H3 119.5 . .
C3 C4 C5 119.03(10) . .
C3 C4 C8 119.15(11) . .
C8 C4 C5 121.81(11) . .
C6 C5 C4 120.65(10) . .
C9 C5 C4 118.66(10) . .
C9 C5 C6 120.56(10) . .
C5 C6 C6 119.94(13) . 2_767
C5 C6 C15 122.23(10) . .
C15 C6 C6 117.84(13) . 2_767
C1 C7 H7 121.0 . .
C1 C7 C8 118.03(12) . .
C8 C7 H7 121.0 . .
C4 C8 H8 119.7 . .
C7 C8 C4 120.60(12) . .
C7 C8 H8 119.7 . .
C5 C9 C10 120.24(10) . .
C5 C9 C14 121.56(11) . .
C14 C9 C10 118.13(11) . .
C11 C10 C9 119.32(11) . .
C15 C10 C9 119.26(11) 2_767 .
C15 C10 C11 121.37(11) 2_767 .
C10 C11 H11 120.7 . .
C12 C11 C10 118.68(11) . .
C12 C11 H11 120.7 . .
F2 C12 C13 117.51(11) . .
C11 C12 F2 118.63(11) . .
C11 C12 C13 123.85(11) . .
C12 C13 H13 120.7 . .
C14 C13 C12 118.58(11) . .
C14 C13 H13 120.7 . .
C9 C14 H14 119.3 . .
C13 C14 C9 121.42(11) . .
C13 C14 H14 119.3 . .
C6 C15 C16 123.38(10) . .
C10 C15 C6 121.88(10) 2_767 .
C10 C15 C16 114.49(10) 2_767 .
N1 C16 C15 170.31(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.3614(14) .
F2 C12 1.3550(14) .
N1 C16 1.1479(16) .
C1 C2 1.374(2) .
C1 C7 1.373(2) .
C2 H2 0.9500 .
C2 C3 1.3880(17) .
C3 H3 0.9500 .
C3 C4 1.3914(18) .
C4 C5 1.4915(16) .
C4 C8 1.3961(17) .
C5 C6 1.4212(16) .
C5 C9 1.3973(16) .
C6 C6 1.451(2) 2_767
C6 C15 1.4222(16) .
C7 H7 0.9500 .
C7 C8 1.3845(17) .
C8 H8 0.9500 .
C9 C10 1.4349(16) .
C9 C14 1.4340(16) .
C10 C11 1.4254(16) .
C10 C15 1.4027(16) 2_767
C11 H11 0.9500 .
C11 C12 1.3483(17) .
C12 C13 1.4094(17) .
C13 H13 0.9500 .
C13 C14 1.3541(17) .
C14 H14 0.9500 .
C15 C10 1.4027(16) 2_767
C15 C16 1.4409(16) .
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
F1 C1 C2 C3 -178.47(11) . .
F1 C1 C7 C8 179.13(12) . .
F2 C12 C13 C14 -179.83(10) . .
C1 C2 C3 C4 -0.68(18) . .
C1 C7 C8 C4 -0.65(19) . .
C2 C1 C7 C8 -1.0(2) . .
C2 C3 C4 C5 -179.41(11) . .
C2 C3 C4 C8 -0.83(18) . .
C3 C4 C5 C6 -70.66(15) . .
C3 C4 C5 C9 105.14(13) . .
C3 C4 C8 C7 1.52(18) . .
C4 C5 C6 C6 171.67(12) . 2_767
C4 C5 C6 C15 -8.40(17) . .
C4 C5 C9 C10 -172.02(10) . .
C4 C5 C9 C14 4.81(16) . .
C5 C4 C8 C7 -179.94(11) . .
C5 C6 C15 C10 175.52(10) . 2_767
C5 C6 C15 C16 -10.53(18) . .
C5 C9 C10 C11 178.25(10) . .
C5 C9 C10 C15 0.63(17) . 2_767
C5 C9 C14 C13 -178.47(11) . .
C6 C5 C9 C10 3.78(17) . .
C6 C5 C9 C14 -179.38(10) . .
C6 C6 C15 C10 -4.55(19) 2_767 2_767
C6 C6 C15 C16 169.40(12) 2_767 .
C7 C1 C2 C3 1.6(2) . .
C8 C4 C5 C6 110.80(13) . .
C8 C4 C5 C9 -73.40(15) . .
C9 C5 C6 C6 -4.04(19) . 2_767
C9 C5 C6 C15 175.88(10) . .
C9 C10 C11 C12 -0.14(17) . .
C10 C9 C14 C13 -1.57(17) . .
C10 C11 C12 F2 179.61(10) . .
C10 C11 C12 C13 -0.88(18) . .
C11 C12 C13 C14 0.65(19) . .
C12 C13 C14 C9 0.62(18) . .
C14 C9 C10 C11 1.31(16) . .
C14 C9 C10 C15 -176.30(10) . 2_767
C15 C10 C11 C12 177.42(11) 2_767 .
