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#$Date: 2019-11-04 17:35:00 +0200 (Mon, 04 Nov 2019) $
#$Revision: 223171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/27/1552742.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_1552742
loop_
_publ_author_name
'Ly, Jack'
'Martin, Kara'
'Thomas, Simil'
'Yamashita, Masataka'
'Yu, Beihang'
'Pointer, Craig A.'
'Yamada, Hiroko'
'Carter, Kenneth R.'
'Parkin, Sean'
'Zhang, Lei'
'Bredas, Jean-Luc'
'Young, Elizabeth R.'
'Briseno, Alejandro L.'
_publ_section_title
;
 Short Excited-State Lifetimes Enable Photo-Oxidatively Stable Rubrene
 Derivatives.
;
_journal_issue                   35
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              7558
_journal_paper_doi               10.1021/acs.jpca.9b04203
_journal_volume                  123
_journal_year                    2019
_chemical_formula_moiety         'C50 H28'
_chemical_formula_sum            'C50 H28'
_chemical_formula_weight         628.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2014/7 and CIFFIX'
_cell_angle_alpha                90
_cell_angle_beta                 91.961(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9506(3)
_cell_length_b                   5.3187(1)
_cell_length_c                   33.0475(7)
_cell_measurement_reflns_used    6482
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      68.09
_cell_measurement_theta_min      2.68
_cell_volume                     3328.99(11)
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2006)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            22145
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.120
_diffrn_reflns_theta_min         2.676
_diffrn_source                   'fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       rod
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0395
_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)+(0.0577P)²+1.4989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2380
_reflns_number_total             2986
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp9b04203_si_005.cif
_cod_data_source_block           x15156
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               1552742
_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   0.876
_shelx_estimated_absorpt_t_max   0.989
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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
C1 C 0.50156(7) 0.6636(2) 0.55058(4) 0.0187(3) Uani 1 1 d . .
C2 C 0.44923(7) 0.8495(2) 0.54399(4) 0.0186(3) Uani 1 1 d . .
C3 C 0.43637(7) 1.0392(3) 0.57335(4) 0.0213(3) Uani 1 1 d . .
H3A H 0.4648 1.0456 0.5976 0.026 Uiso 1 1 calc R U
C4 C 0.38395(7) 1.2110(3) 0.56717(4) 0.0227(3) Uani 1 1 d . .
H4A H 0.3769 1.3384 0.5868 0.027 Uiso 1 1 calc R U
C5 C 0.33988(7) 1.2013(3) 0.53181(4) 0.0226(3) Uani 1 1 d . .
H5A H 0.3027 1.3199 0.5281 0.027 Uiso 1 1 calc R U
C6 C 0.35030(8) 1.0232(3) 0.50301(4) 0.0216(3) Uani 1 1 d . .
H6A H 0.3199 1.0177 0.4796 0.026 Uiso 1 1 calc R U
C7 C 0.40622(7) 0.8447(2) 0.50761(4) 0.0185(3) Uani 1 1 d . .
C8 C 0.41856(7) 0.6593(2) 0.47806(4) 0.0187(3) Uani 1 1 d . .
C9 C 0.47887(7) 0.4994(2) 0.48146(4) 0.0180(3) Uani 1 1 d . .
C10 C 0.52727(7) 0.6275(3) 0.59114(4) 0.0201(3) Uani 1 1 d . .
C11 C 0.54004(7) 0.5874(3) 0.62665(4) 0.0224(3) Uani 1 1 d . .
C12 C 0.56074(8) 0.5319(3) 0.66757(4) 0.0233(3) Uani 1 1 d . .
C13 C 0.60379(9) 0.3239(3) 0.67659(5) 0.0299(4) Uani 1 1 d . .
H13A H 0.6171 0.2134 0.6556 0.036 Uiso 1 1 calc R U
C14 C 0.62701(9) 0.2793(3) 0.71606(5) 0.0364(4) Uani 1 1 d . .
H14A H 0.6565 0.1387 0.7220 0.044 Uiso 1 1 calc R U
C15 C 0.60753(10) 0.4389(3) 0.74700(5) 0.0383(4) Uani 1 1 d . .
H15A H 0.6246 0.4100 0.7740 0.046 Uiso 1 1 calc R U
C16 C 0.56329(10) 0.6398(3) 0.73848(5) 0.0358(4) Uani 1 1 d . .
H16A H 0.5485 0.7453 0.7598 0.043 Uiso 1 1 calc R U
C17 C 0.54046(9) 0.6880(3) 0.69909(5) 0.0286(4) Uani 1 1 d . .
H17A H 0.5108 0.8284 0.6934 0.034 Uiso 1 1 calc R U
C18 C 0.36604(7) 0.6245(3) 0.44675(4) 0.0197(3) Uani 1 1 d . .
C19 C 0.31752(7) 0.5907(3) 0.42264(4) 0.0206(3) Uani 1 1 d . .
C20 C 0.26504(7) 0.5451(3) 0.39144(4) 0.0203(3) Uani 1 1 d . .
C21 C 0.20903(8) 0.7127(3) 0.38537(4) 0.0229(3) Uani 1 1 d . .
H21A H 0.2049 0.8545 0.4026 0.027 Uiso 1 1 calc R U
C22 C 0.15944(8) 0.6724(3) 0.35419(5) 0.0285(4) Uani 1 1 d . .
H22A H 0.1212 0.7863 0.3502 0.034 Uiso 1 1 calc R U
C23 C 0.16542(9) 0.4676(3) 0.32888(5) 0.0319(4) Uani 1 1 d . .
H23A H 0.1317 0.4420 0.3073 0.038 Uiso 1 1 calc R U
C24 C 0.22074(9) 0.2990(3) 0.33491(5) 0.0314(4) Uani 1 1 d . .
H24A H 0.2247 0.1578 0.3175 0.038 Uiso 1 1 calc R U
C25 C 0.27006(8) 0.3361(3) 0.36618(5) 0.0261(3) Uani 1 1 d . .
H25A H 0.3074 0.2191 0.3705 0.031 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 0.0181 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'
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 C10 117.10(12) . .
C2 C1 C9 120.65(13) . 5_666
C10 C1 C9 121.84(12) . 5_666
C1 C2 C3 121.72(13) . .
C1 C2 C7 119.64(12) . .
C3 C2 C7 118.61(13) . .
C4 C3 C2 120.94(14) . .
C4 C3 H3A 119.5 . .
C2 C3 H3A 119.5 . .
C3 C4 C5 120.50(13) . .
C3 C4 H4A 119.8 . .
C5 C4 H4A 119.8 . .
C6 C5 C4 120.47(13) . .
C6 C5 H5A 119.8 . .
C4 C5 H5A 119.8 . .
C5 C6 C7 120.89(14) . .
C5 C6 H6A 119.6 . .
C7 C6 H6A 119.6 . .
C8 C7 C6 122.06(13) . .
C8 C7 C2 119.38(12) . .
C6 C7 C2 118.52(13) . .
C7 C8 C18 117.71(12) . .
C7 C8 C9 120.87(13) . .
C18 C8 C9 121.23(12) . .
C8 C9 C1 122.13(13) . 5_666
C8 C9 C9 119.03(15) . 5_666
C1 C9 C9 118.84(15) 5_666 5_666
C11 C10 C1 171.29(15) . .
C10 C11 C12 175.16(15) . .
C17 C12 C13 118.96(14) . .
C17 C12 C11 120.69(14) . .
C13 C12 C11 120.31(14) . .
C14 C13 C12 120.04(15) . .
C14 C13 H13A 120.0 . .
C12 C13 H13A 120.0 . .
C13 C14 C15 120.37(16) . .
C13 C14 H14A 119.8 . .
C15 C14 H14A 119.8 . .
C16 C15 C14 119.84(15) . .
C16 C15 H15A 120.1 . .
C14 C15 H15A 120.1 . .
C15 C16 C17 120.26(16) . .
C15 C16 H16A 119.9 . .
C17 C16 H16A 119.9 . .
C16 C17 C12 120.48(15) . .
C16 C17 H17A 119.8 . .
C12 C17 H17A 119.8 . .
C19 C18 C8 174.57(14) . .
C18 C19 C20 174.63(15) . .
C25 C20 C21 119.33(14) . .
C25 C20 C19 120.48(13) . .
C21 C20 C19 120.17(13) . .
C22 C21 C20 120.07(14) . .
C22 C21 H21A 120.0 . .
C20 C21 H21A 120.0 . .
C23 C22 C21 120.28(15) . .
C23 C22 H22A 119.9 . .
C21 C22 H22A 119.9 . .
C22 C23 C24 120.00(15) . .
C22 C23 H23A 120.0 . .
C24 C23 H23A 120.0 . .
C25 C24 C23 120.14(15) . .
C25 C24 H24A 119.9 . .
C23 C24 H24A 119.9 . .
C24 C25 C20 120.17(14) . .
C24 C25 H25A 119.9 . .
C20 C25 H25A 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.412(2) .
C1 C10 1.4234(19) .
C1 C9 1.4275(19) 5_666
C2 C3 1.4265(19) .
C2 C7 1.4296(19) .
C3 C4 1.360(2) .
C3 H3A 0.9500 .
C4 C5 1.414(2) .
C4 H4A 0.9500 .
C5 C6 1.362(2) .
C5 H5A 0.9500 .
C6 C7 1.427(2) .
C6 H6A 0.9500 .
C7 C8 1.413(2) .
C8 C18 1.4232(19) .
C8 C9 1.426(2) .
C9 C1 1.4274(19) 5_666
C9 C9 1.441(3) 5_666
C10 C11 1.209(2) .
C11 C12 1.426(2) .
C12 C17 1.396(2) .
C12 C13 1.400(2) .
C13 C14 1.383(2) .
C13 H13A 0.9500 .
C14 C15 1.389(3) .
C14 H14A 0.9500 .
C15 C16 1.381(3) .
C15 H15A 0.9500 .
C16 C17 1.382(2) .
C16 H16A 0.9500 .
C17 H17A 0.9500 .
C18 C19 1.209(2) .
C19 C20 1.428(2) .
C20 C25 1.395(2) .
C20 C21 1.395(2) .
C21 C22 1.387(2) .
C21 H21A 0.9500 .
C22 C23 1.380(2) .
C22 H22A 0.9500 .
C23 C24 1.389(2) .
C23 H23A 0.9500 .
C24 C25 1.384(2) .
C24 H24A 0.9500 .
C25 H25A 0.9500 .
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
C10 C1 C2 C3 17.11(19) . .
C9 C1 C2 C3 -170.11(12) 5_666 .
C10 C1 C2 C7 -160.93(12) . .
C9 C1 C2 C7 11.85(19) 5_666 .
C1 C2 C3 C4 -177.47(13) . .
C7 C2 C3 C4 0.6(2) . .
C2 C3 C4 C5 1.5(2) . .
C3 C4 C5 C6 -1.4(2) . .
C4 C5 C6 C7 -0.7(2) . .
C5 C6 C7 C8 -179.47(13) . .
C5 C6 C7 C2 2.8(2) . .
C1 C2 C7 C8 -2.39(19) . .
C3 C2 C7 C8 179.51(12) . .
C1 C2 C7 C6 175.43(12) . .
C3 C2 C7 C6 -2.68(18) . .
C6 C7 C8 C18 -11.20(19) . .
C2 C7 C8 C18 166.53(12) . .
C6 C7 C8 C9 173.73(12) . .
C2 C7 C8 C9 -8.5(2) . .
C7 C8 C9 C1 -170.61(12) . 5_666
C18 C8 C9 C1 14.5(2) . 5_666
C7 C8 C9 C9 10.0(2) . 5_666
C18 C8 C9 C9 -164.93(15) . 5_666
C17 C12 C13 C14 -1.6(2) . .
C11 C12 C13 C14 176.28(15) . .
C12 C13 C14 C15 0.4(2) . .
C13 C14 C15 C16 1.6(3) . .
C14 C15 C16 C17 -2.4(3) . .
C15 C16 C17 C12 1.2(3) . .
C13 C12 C17 C16 0.8(2) . .
C11 C12 C17 C16 -177.06(15) . .
C25 C20 C21 C22 -0.7(2) . .
C19 C20 C21 C22 177.84(13) . .
C20 C21 C22 C23 -0.4(2) . .
C21 C22 C23 C24 0.9(2) . .
C22 C23 C24 C25 -0.2(2) . .
C23 C24 C25 C20 -0.9(2) . .
C21 C20 C25 C24 1.4(2) . .
C19 C20 C25 C24 -177.18(14) . .
