#------------------------------------------------------------------------------
#$Date: 2019-11-08 04:22:00 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/00/1550015.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_1550015
loop_
_publ_author_name
'Li, Jing'
'Duchemin, Ivan'
'Roscioni, Otello Maria'
'Friederich, Pascal'
'Anderson, Marie'
'Da Como, Enrico'
'Kociok-Köhn, Gabriele'
'Wenzel, Wolfgang'
'Zannoni, Claudio'
'Beljonne, David'
'Blase, Xavier'
'D'Avino, Gabriele'
_publ_section_title
;
 Host dependence of the electron affinity of molecular dopants
;
_journal_issue                   1
_journal_name_full               'Materials Horizons'
_journal_page_first              107
_journal_paper_doi               10.1039/C8MH00921J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C16 F6 N4'
_chemical_formula_sum            'C16 F6 N4'
_chemical_formula_weight         362.20
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-08-01 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   17.533(4)
_cell_length_b                   17.533(4)
_cell_length_c                   11.484(3)
_cell_measurement_reflns_used    1154
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      69.6600
_cell_measurement_theta_min      4.7510
_cell_volume                     3057.3(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
 'SHELXL-2018 (Sheldrick, 2018)
;
_computing_structure_refinement
;SHELXL-2018/3 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_structure_solution
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5752
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.510
_diffrn_reflns_theta_min         4.828
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.507
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark green'
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             1602
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00049(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         1300
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0585
_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)+(0.1070P)²+1.9608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1005
_reflns_number_total             1300
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8mh00921j2.cif
_cod_data_source_block           F6TCNNQ
_cod_depositor_comments          'Adding full bibliography for 1550015.cif.'
_cod_original_cell_volume        3057.3(16)
_cod_database_code               1550015
_shelx_shelxl_version_number     2018/3
_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   0.864
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6158(10) 0.4570(9) 0.5281(15) 0.054(3) Uani 0.780(8) 1 d . P A 1
C2 C 0.5495(2) 0.4310(2) 0.4534(3) 0.0464(11) Uani 0.780(8) 1 d . P A 1
C3 C 0.4912(4) 0.4670(3) 0.4557(4) 0.0452(13) Uani 0.780(8) 1 d . P A 1
C4 C 0.4224(3) 0.4428(3) 0.3815(4) 0.0491(11) Uani 0.780(8) 1 d . P A 1
C5 C 0.3633(4) 0.4779(4) 0.3829(5) 0.0480(13) Uani 0.780(8) 1 d . P A 1
C7 C 0.2656(8) 0.3833(6) 0.2238(12) 0.060(2) Uani 0.780(8) 1 d . P A 1
C8 C 0.2421(7) 0.4950(7) 0.3000(10) 0.055(2) Uani 0.780(8) 1 d . P A 1
N1 N 0.2340(8) 0.3214(9) 0.1621(12) 0.083(3) Uani 0.780(8) 1 d . P A 1
N2 N 0.1977(5) 0.5213(6) 0.2830(7) 0.0695(18) Uani 0.780(8) 1 d . P A 1
F1 F 0.6679(2) 0.42190(16) 0.5202(2) 0.0561(8) Uani 0.780(8) 1 d . P A 1
F3 F 0.4068(3) 0.3834(3) 0.2974(4) 0.0581(13) Uani 0.780(8) 1 d . P A 1
C1A C 0.5928(12) 0.4885(14) 0.5513(17) 0.063(5) Uani 0.220(8) 1 d U P A 2
C2A C 0.5199(12) 0.4713(13) 0.4846(15) 0.047(6) Uani 0.220(8) 1 d U P A 2
C3A C 0.4830(8) 0.4131(8) 0.3928(11) 0.048(4) Uani 0.220(8) 1 d U P A 2
C4A C 0.4138(14) 0.4032(19) 0.334(2) 0.044(5) Uani 0.220(8) 1 d U P A 2
C5A C 0.3720(13) 0.4543(13) 0.3629(19) 0.046(5) Uani 0.220(8) 1 d U P A 2
C7A C 0.251(2) 0.361(2) 0.232(3) 0.039(5) Uani 0.220(8) 1 d U P A 2
C8A C 0.262(2) 0.491(3) 0.300(4) 0.051(8) Uani 0.220(8) 1 d U P A 2
F1A F 0.6287(18) 0.4401(16) 0.524(3) 0.055(6) Uani 0.220(8) 1 d U P A 2
F3A F 0.3803(8) 0.3431(9) 0.2470(11) 0.070(3) Uani 0.220(8) 1 d U P A 2
N1A N 0.209(3) 0.319(3) 0.165(4) 0.076(9) Uani 0.220(8) 1 d U P A 2
N2A N 0.2251(19) 0.540(2) 0.304(3) 0.067(7) Uani 0.220(8) 1 d U P A 2
C6 C 0.2960(2) 0.4507(2) 0.3054(2) 0.0560(7) Uani 1 1 d . . . .
F2 F 0.53287(12) 0.36953(11) 0.37208(14) 0.0602(6) 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 0.0181 0.0091 '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'
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
C2 C1 F1 118.7(11) . .
C2 C1 C5 124.4(9) . 10_666
F1 C1 C5 116.9(11) . 10_666
C1 C2 F2 121.7(6) . .
C1 C2 C3 121.8(6) . .
F2 C2 C3 116.5(3) . .
C4 C3 C2 124.2(5) . .
C4 C3 C3 119.3(6) . 10_666
C2 C3 C3 116.5(6) . 10_666
F3 C4 C3 119.8(5) . .
F3 C4 C5 115.2(5) . .
C3 C4 C5 125.0(5) . .
C6 C5 C1 125.2(7) . 10_666
C6 C5 C4 121.6(5) . .
C1 C5 C4 113.1(7) 10_666 .
N1 C7 C6 173.7(12) . .
N2 C8 C6 170.7(10) . .
C5A C1A F1A 118(3) 10_666 .
C5A C1A C2A 127(2) 10_666 .
F1A C1A C2A 114(2) . .
C3A C2A C1A 129(2) . .
C4A C3A C2A 123.3(19) . .
C4A C3A F2 127.3(17) . .
C2A C3A F2 109.4(12) . .
C3A C4A F3A 120(2) . .
C3A C4A C5A 121(3) . .
F3A C4A C5A 120(2) . .
C1A C5A C4A 117(2) 10_666 .
C1A C5A C6 116.1(17) 10_666 .
C4A C5A C6 126.9(18) . .
N1A C7A C6 154(4) . .
C6 C8A N2A 174(5) . .
C5 C6 C7 129.6(7) . .
C8A C6 C5A 139(2) . .
C5 C6 C8 120.5(5) . .
C7 C6 C8 109.9(7) . .
C8A C6 C7A 115(3) . .
C5A C6 C7A 106.0(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.329(16) .
C1 F1 1.336(11) .
C1 C5 1.436(14) 10_666
C2 F2 1.344(4) .
C2 C3 1.445(6) .
C3 C4 1.360(8) .
C3 C3 1.452(10) 10_666
C4 F3 1.345(5) .
C4 C5 1.447(6) .
C5 C6 1.359(7) .
C7 N1 1.178(17) .
C7 C6 1.389(13) .
C8 N2 1.104(15) .
C8 C6 1.494(10) .
C1A C5A 1.32(3) 10_666
C1A F1A 1.32(2) .
C1A C2A 1.39(3) .
C2A C3A 1.38(2) .
C2A C2A 1.53(4) 10_666
C3A C4A 1.32(3) .
C3A F2 1.440(11) .
C4A F3A 1.35(3) .
C4A C5A 1.45(3) .
C5A C6 1.46(2) .
C7A N1A 1.06(6) .
C7A C6 1.60(4) .
C8A C6 1.13(3) .
C8A N2A 1.31(5) .
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 F2 1.2(18) . .
C5 C1 C2 F2 -179.8(9) 10_666 .
F1 C1 C2 C3 -179.1(9) . .
C5 C1 C2 C3 -0.1(18) 10_666 .
C1 C2 C3 C4 -180.0(9) . .
F2 C2 C3 C4 -0.3(6) . .
C1 C2 C3 C3 -0.2(11) . 10_666
F2 C2 C3 C3 179.5(5) . 10_666
C2 C3 C4 F3 -1.8(7) . .
C3 C3 C4 F3 178.4(5) 10_666 .
C2 C3 C4 C5 179.7(4) . .
C3 C3 C4 C5 -0.1(8) 10_666 .
F3 C4 C5 C6 1.2(7) . .
C3 C4 C5 C6 179.8(4) . .
F3 C4 C5 C1 -178.2(8) . 10_666
C3 C4 C5 C1 0.3(10) . 10_666
C5A C1A C2A C3A 178.4(17) 10_666 .
F1A C1A C2A C3A -2(3) . .
C5A C1A C2A C2A 2(3) 10_666 10_666
F1A C1A C2A C2A -179(2) . 10_666
C1A C2A C3A C4A -178.7(17) . .
C2A C2A C3A C4A -2(3) 10_666 .
C1A C2A C3A F2 0(2) . .
C2A C2A C3A F2 176.1(15) 10_666 .
C2A C3A C4A F3A -178.2(15) . .
F2 C3A C4A F3A 4(3) . .
C2A C3A C4A C5A 0(3) . .
F2 C3A C4A C5A -178.0(13) . .
C3A C4A C5A C1A 1(3) . 10_666
F3A C4A C5A C1A 179.6(16) . 10_666
C3A C4A C5A C6 179.7(14) . .
F3A C4A C5A C6 -2(3) . .
C1 C5 C6 C7 -173.5(10) 10_666 .
C4 C5 C6 C7 7.1(10) . .
C1 C5 C6 C8 6.3(12) 10_666 .
C4 C5 C6 C8 -173.1(6) . .
C1A C5A C6 C8A 14(4) 10_666 .
C4A C5A C6 C8A -164(3) . .
C1A C5A C6 C7A -165.0(19) 10_666 .
C4A C5A C6 C7A 17(2) . .
N1A C7A C6 C8A 19(10) . .
N1A C7A C6 C5A -161(9) . .
