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#$Date: 2019-11-11 16:05:22 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226494 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/49/4034988.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_4034988
loop_
_publ_author_name
'Purvis, Lafe J.'
'Gu, Xingxian'
'Ghosh, Soumen'
'Zhang, Zhuoran'
'Cramer, Christopher J.'
'Douglas, Christopher J.'
_publ_section_title
;
 Synthesis and Characterization of Electron-Deficient Asymmetrically
 Substituted Diarylindenotetracenes.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1828
_journal_page_last               1841
_journal_paper_doi               10.1021/acs.joc.7b02756
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         C36H20F2
_chemical_formula_sum            'C36 H20 F2'
_chemical_formula_weight         490.52
_chemical_melting_point          Decomp
_chemical_name_common            DiFMonoPhIndenotetracene
_chemical_name_systematic
2-fluoro-9-(4-fluorophenyl)-10-phenylindeno[1,2,3-fg]tetracene
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.70
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.943
_cell_length_b                   20.012
_cell_length_c                   7.763
_cell_measurement_reflns_used    2326
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      74.715
_cell_measurement_theta_min      2.831
_cell_volume                     2301.271
_computing_cell_refinement       'Saint, Bruker'
_computing_data_collection       'APEXII, Bruker'
_computing_data_reduction        'Saint, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      122(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Photon CCD'
_diffrn_measurement_method       'area detector, omega scnas per phi'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14083
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.715
_diffrn_reflns_theta_min         4.419
_diffrn_source                   'normal-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.7538
_exptl_transmission_factor_min   0.6925
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0395
_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)+(0.0587P)²+1.3885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2151
_reflns_number_total             2326
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02756_si_002.cif
_cod_data_source_block           15242_0m-auto_cmpd_8c
_cod_original_cell_volume        2301.4
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4034988
_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   0.666
_shelx_estimated_absorpt_t_max   0.930
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.40798(9) 0.91289(6) 0.85025(19) 0.0339(3) Uani 1 1 d . . . . .
F2 F 0.40874(11) 0.97743(8) 0.8814(3) 0.0453(4) Uani 0.5 1 d . . P A 1
H02 H 0.4068(12) 0.969(5) 0.875(4) 0.25(5) Uiso 0.5 1 d R . P A 2
C3 C 0.47436(9) 0.87662(6) 0.98348(19) 0.0320(3) Uani 1 1 d . . . . .
H11 H 0.5159 0.8983 1.0897 0.039(4) Uiso 1 1 calc R . . . .
C4 C 0.47967(8) 0.80817(6) 0.96036(16) 0.0265(3) Uani 1 1 d . . . . .
H13 H 0.5247 0.7829 1.0524 0.034(4) Uiso 1 1 calc R . . . .
C5 C 0.41978(7) 0.77605(5) 0.80382(15) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.42551(7) 0.70229(5) 0.78041(14) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.5000 0.67101(7) 0.7500 0.0214(3) Uani 1 2 d S T P . .
C8 C 0.35275(8) 0.81408(6) 0.67191(17) 0.0288(3) Uani 1 1 d . . . . .
H12 H 0.3110 0.7928 0.5653 0.035(4) Uiso 1 1 calc R . . . .
C9 C 0.34641(9) 0.88243(6) 0.69458(19) 0.0333(3) Uani 1 1 d . . . . .
H3 H 0.3006 0.9079 0.6048 0.044(4) Uiso 1 1 calc R . . . .
C10 C 0.35578(7) 0.66263(6) 0.80022(15) 0.0241(3) Uani 1 1 d . . . . .
C11 C 0.35631(7) 0.59025(6) 0.78953(15) 0.0246(3) Uani 1 1 d . . . . .
C12 C 0.28283(8) 0.55380(6) 0.80937(17) 0.0306(3) Uani 1 1 d . . . . .
H4 H 0.2814 0.5065 0.7975 0.044(4) Uiso 1 1 calc R . . . .
C13 C 0.21521(8) 0.58508(7) 0.84462(18) 0.0338(3) Uani 1 1 d . . . . .
H5 H 0.1676 0.5597 0.8578 0.039(4) Uiso 1 1 calc R . . . .
C14 C 0.21565(8) 0.65566(7) 0.86176(18) 0.0322(3) Uani 1 1 d . . . . .
H7 H 0.1688 0.6773 0.8886 0.038(4) Uiso 1 1 calc R . . . .
C15 C 0.28267(8) 0.69263(6) 0.84000(16) 0.0283(3) Uani 1 1 d . . . . .
H6 H 0.2813 0.7398 0.8514 0.037(4) Uiso 1 1 calc R . . . .
C16 C 0.43053(7) 0.55973(5) 0.76739(14) 0.0237(3) Uani 1 1 d . . . . .
C17 C 0.5000 0.59976(8) 0.7500 0.0221(3) Uani 1 2 d S T P . .
C18 C 0.45766(8) 0.48959(5) 0.76099(15) 0.0259(3) Uani 1 1 d . . . . .
C19 C 0.41604(9) 0.42931(6) 0.77269(16) 0.0310(3) Uani 1 1 d . . . . .
H8 H 0.3597 0.4287 0.7884 0.026(3) Uiso 1 1 calc R . . . .
C20 C 0.45915(10) 0.37021(6) 0.76080(17) 0.0343(3) Uani 1 1 d . . . . .
F1 F 0.41144(12) 0.31333(7) 0.7702(2) 0.0391(4) Uani 0.5 1 d . . P B 1
H01 H 0.4321 0.3291 0.7675 0.18(4) Uiso 0.5 1 d R . P B 2
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'
H H 0.0000 0.0000 '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
F2 C2 C3 115.25(14) . .
F2 C2 C9 123.30(13) . .
C3 C2 C9 121.45(11) . .
C3 C2 H02 116.7 . .
C9 C2 H02 121.9 . .
C2 C3 C4 119.23(12) . .
C2 C3 H11 120.4 . .
C4 C3 H11 120.4 . .
C3 C4 C5 120.85(11) . .
C3 C4 H13 119.6 . .
C5 C4 H13 119.6 . .
C4 C5 C8 118.58(10) . .
C4 C5 C6 120.56(10) . .
C8 C5 C6 120.83(10) . .
C10 C6 C7 120.13(11) . .
C10 C6 C5 116.97(10) . .
C7 C6 C5 122.80(10) . .
C17 C7 C6 115.82(7) . .
C17 C7 C6 115.82(7) . 2_656
C6 C7 C6 128.35(14) . 2_656
C9 C8 C5 120.98(11) . .
C9 C8 H12 119.5 . .
C5 C8 H12 119.5 . .
C2 C9 C8 118.90(11) . .
C2 C9 H3 120.6 . .
C8 C9 H3 120.6 . .
C6 C10 C15 121.16(10) . .
C6 C10 C11 122.04(10) . .
C15 C10 C11 116.75(10) . .
C16 C11 C12 123.55(11) . .
C16 C11 C10 117.80(10) . .
C12 C11 C10 118.60(10) . .
C13 C12 C11 121.80(11) . .
C13 C12 H4 119.1 . .
C11 C12 H4 119.1 . .
C12 C13 C14 120.05(11) . .
C12 C13 H5 120.0 . .
C14 C13 H5 120.0 . .
C15 C14 C13 120.45(11) . .
C15 C14 H7 119.8 . .
C13 C14 H7 119.8 . .
C14 C15 C10 122.28(11) . .
C14 C15 H6 118.9 . .
C10 C15 H6 118.9 . .
C11 C16 C17 119.54(11) . .
C11 C16 C18 133.80(10) . .
C17 C16 C18 106.64(10) . .
C16 C17 C16 110.94(14) 2_656 .
C16 C17 C7 124.53(7) 2_656 .
C16 C17 C7 124.53(7) . .
C19 C18 C18 120.20(8) . 2_656
C19 C18 C16 131.91(12) . .
C18 C18 C16 107.89(6) 2_656 .
C20 C19 C18 118.23(13) . .
C20 C19 H8 120.9 . .
C18 C19 H8 120.9 . .
C20 C20 F1 124.76(9) 2_656 .
C20 C20 C19 121.56(8) 2_656 .
F1 C20 C19 113.67(14) . .
C20 C20 H01 118.9 2_656 .
C19 C20 H01 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 F2 1.313(2) .
C2 C3 1.3811(19) .
C2 C9 1.3851(19) .
C2 H02 1.14(11) .
C3 C4 1.3882(16) .
C3 H11 0.9500 .
C4 C5 1.3942(16) .
C4 H13 0.9500 .
C5 C8 1.4003(16) .
C5 C6 1.4941(15) .
C6 C10 1.4198(15) .
C6 C7 1.4371(12) .
C7 C17 1.426(2) .
C7 C6 1.4372(12) 2_656
C8 C9 1.3876(17) .
C8 H12 0.9500 .
C9 H3 0.9500 .
C10 C15 1.4424(16) .
C10 C11 1.4511(16) .
C11 C16 1.3976(16) .
C11 C12 1.4360(16) .
C12 C13 1.3591(18) .
C12 H4 0.9500 .
C13 C14 1.4185(19) .
C13 H5 0.9500 .
C14 C15 1.3606(17) .
C14 H7 0.9500 .
C15 H6 0.9500 .
C16 C17 1.4132(14) .
C16 C18 1.4750(15) .
C17 C16 1.4131(14) 2_656
C18 C19 1.3958(16) .
C18 C18 1.422(2) 2_656
C19 C20 1.3882(18) .
C19 H8 0.9500 .
C20 C20 1.373(3) 2_656
C20 F1 1.386(2) .
C20 H01 0.9386 .
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
F2 C2 C3 C4 -178.91(13) . .
C9 C2 C3 C4 0.28(19) . .
C2 C3 C4 C5 0.84(18) . .
C3 C4 C5 C8 -1.36(17) . .
C3 C4 C5 C6 -179.61(11) . .
C4 C5 C6 C10 108.53(12) . .
C8 C5 C6 C10 -69.68(14) . .
C4 C5 C6 C7 -67.87(14) . .
C8 C5 C6 C7 113.91(11) . .
C10 C6 C7 C17 -2.67(10) . .
C5 C6 C7 C17 173.62(7) . .
C10 C6 C7 C6 177.33(10) . 2_656
C5 C6 C7 C6 -6.38(7) . 2_656
C4 C5 C8 C9 0.79(17) . .
C6 C5 C8 C9 179.04(11) . .
F2 C2 C9 C8 178.28(14) . .
C3 C2 C9 C8 -0.83(19) . .
C5 C8 C9 C2 0.29(18) . .
C7 C6 C10 C15 176.88(9) . .
C5 C6 C10 C15 0.38(15) . .
C7 C6 C10 C11 -0.45(14) . .
C5 C6 C10 C11 -176.95(9) . .
C6 C10 C11 C16 2.94(15) . .
C15 C10 C11 C16 -174.50(10) . .
C6 C10 C11 C12 -179.45(10) . .
C15 C10 C11 C12 3.11(15) . .
C16 C11 C12 C13 174.94(11) . .
C10 C11 C12 C13 -2.52(17) . .
C11 C12 C13 C14 0.37(19) . .
C12 C13 C14 C15 1.13(19) . .
C13 C14 C15 C10 -0.38(18) . .
C6 C10 C15 C14 -179.21(11) . .
C11 C10 C15 C14 -1.75(16) . .
C12 C11 C16 C17 -179.62(9) . .
C10 C11 C16 C17 -2.14(14) . .
C12 C11 C16 C18 -1.30(19) . .
C10 C11 C16 C18 176.18(11) . .
C11 C16 C17 C16 178.85(11) . 2_656
C18 C16 C17 C16 0.11(5) . 2_656
C11 C16 C17 C7 -1.15(11) . .
C18 C16 C17 C7 -179.89(5) . .
C6 C7 C17 C16 -176.42(7) . 2_656
C6 C7 C17 C16 3.58(7) 2_656 2_656
C6 C7 C17 C16 3.58(7) . .
C6 C7 C17 C16 -176.42(7) 2_656 .
C11 C16 C18 C19 1.1(2) . .
C17 C16 C18 C19 179.58(11) . .
C11 C16 C18 C18 -178.77(12) . 2_656
C17 C16 C18 C18 -0.29(13) . 2_656
C18 C18 C19 C20 -0.51(19) 2_656 .
C16 C18 C19 C20 179.63(11) . .
C18 C19 C20 C20 0.4(2) . 2_656
C18 C19 C20 F1 -178.76(11) . .
