#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:18:27 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236457 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/40/1554028.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_1554028
loop_
_publ_author_name
'Hathwar, Venkatesha R.'
'Thomsen, Maja K.'
'Mamakhel, Mohammad Aref H.'
'Filsø, Mette Ø'
'Overgaard, Jacob'
'Iversen, Bo B.'
_publ_section_title
;
 Electron Density Analysis of the "O-O" Charge-Shift Bonding in
 Rubrene Endoperoxide.
;
_journal_issue                   38
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              7510
_journal_page_last               7518
_journal_paper_doi               10.1021/acs.jpca.6b06588
_journal_volume                  120
_journal_year                    2016
_chemical_formula_moiety         'C42 H30, C8 H8'
_chemical_formula_sum            'C50 H38'
_chemical_formula_weight         638.80
_space_group_crystal_system      trigonal
_space_group_IT_number           165
_space_group_name_Hall           '-P 3 2"c'
_space_group_name_H-M_alt        'P -3 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   25.335(5)
_cell_length_b                   25.335(5)
_cell_length_c                   9.7336(14)
_cell_measurement_reflns_used    3575
_cell_measurement_temperature    100.0(12)
_cell_measurement_theta_max      23.0720
_cell_measurement_theta_min      2.4530
_cell_volume                     5410.6(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Agilent Atlas CCD-area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.577
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Supernova diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.577
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22153
_diffrn_reflns_point_group_measured_fraction_full 0.577
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         20.811
_diffrn_reflns_theta_min         2.456
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Agilent Mova'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2028
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0590
_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)+(0.0544P)²+9.9406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                1530
_reflns_number_total             1892
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Compound_3.cif
_cod_data_source_block           compond_3
_cod_original_cell_volume        5411(2)
_cod_database_code               1554028
_chemical_oxdiff_formula         'C42 H24'
_chemical_oxdiff_usercomment     'green needles from rubrene re-xtallisation'
_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.
;
_shelxl_version_number           2014-1
_thetm01_alert_3_a_compound_3
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength =    0.4999
RESPONSE:  Crystals were small and didn't scatter well at higher angle regions. So data was truncated to avoid the systematic errors arising from the poor data.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, 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
C1 C 0.63036(15) 0.59937(15) 0.2585(3) 0.0182(8) Uani 1 1 d . . .
C2 C 0.57333(15) 0.53874(15) 0.2596(3) 0.0186(8) Uani 1 1 d . . .
C3 C 0.56287(15) 0.48104(15) 0.2728(3) 0.0185(9) Uani 1 1 d . . .
C4 C 0.61513(15) 0.46964(14) 0.2612(3) 0.0182(9) Uani 1 1 d . . .
C5 C 0.65481(15) 0.49177(15) 0.1493(4) 0.0229(9) Uani 1 1 d . . .
H5 H 0.6494 0.5155 0.0813 0.027 Uiso 1 1 calc R U .
C6 C 0.70216(16) 0.47937(16) 0.1364(4) 0.0274(9) Uani 1 1 d . . .
H6 H 0.7288 0.4946 0.0596 0.033 Uiso 1 1 calc R U .
C7 C 0.71073(16) 0.44505(16) 0.2348(4) 0.0310(10) Uani 1 1 d . . .
H7 H 0.7430 0.4365 0.2256 0.037 Uiso 1 1 calc R U .
C8 C 0.67191(16) 0.42318(15) 0.3472(4) 0.0271(9) Uani 1 1 d . . .
H8 H 0.6781 0.4002 0.4157 0.033 Uiso 1 1 calc R U .
C9 C 0.62410(15) 0.43469(15) 0.3602(4) 0.0228(9) Uani 1 1 d . . .
H9 H 0.5973 0.4188 0.4365 0.027 Uiso 1 1 calc R U .
C10 C 0.50275(14) 0.42588(15) 0.2983(3) 0.0181(9) Uani 1 1 d . . .
C11 C 0.48907(15) 0.37049(15) 0.2373(3) 0.0205(9) Uani 1 1 d . . .
H11 H 0.5179 0.3692 0.1771 0.025 Uiso 1 1 calc R U .
C12 C 0.43452(15) 0.31751(16) 0.2623(3) 0.0237(9) Uani 1 1 d . . .
H12 H 0.4263 0.2803 0.2205 0.028 Uiso 1 1 calc R U .
C13 C 0.39205(16) 0.31924(16) 0.3486(4) 0.0245(9) Uani 1 1 d . . .
H13 H 0.3546 0.2830 0.3665 0.029 Uiso 1 1 calc R U .
C14 C 0.40389(15) 0.37348(15) 0.4090(3) 0.0223(9) Uani 1 1 d . . .
H14 H 0.3742 0.3746 0.4667 0.027 Uiso 1 1 calc R U .
C15 C 0.45914(15) 0.42639(15) 0.3854(3) 0.0191(9) Uani 1 1 d . . .
H15 H 0.4673 0.4633 0.4289 0.023 Uiso 1 1 calc R U .
C16 C 0.69597(15) 0.62174(15) 0.2758(3) 0.0196(9) Uani 1 1 d . . .
C17 C 0.71790(16) 0.59990(16) 0.3809(4) 0.0242(9) Uani 1 1 d . . .
H17 H 0.6900 0.5682 0.4395 0.029 Uiso 1 1 calc R U .
C18 C 0.78015(16) 0.62437(16) 0.3996(4) 0.0304(10) Uani 1 1 d . . .
H18 H 0.7947 0.6096 0.4713 0.036 Uiso 1 1 calc R U .
C19 C 0.82099(17) 0.67011(18) 0.3142(4) 0.0370(11) Uani 1 1 d . . .
H19 H 0.8635 0.6867 0.3273 0.044 Uiso 1 1 calc R U .
C20 C 0.80013(16) 0.69181(17) 0.2098(4) 0.0335(10) Uani 1 1 d . . .
H20 H 0.8283 0.7232 0.1509 0.040 Uiso 1 1 calc R U .
C21 C 0.73816(15) 0.66789(16) 0.1909(4) 0.0240(9) Uani 1 1 d . . .
H21 H 0.7242 0.6832 0.1190 0.029 Uiso 1 1 calc R U .
C22 C 0.2005(3) 0.2005(3) 0.2500 0.081(2) Uiso 1 2 d S . P
C23 C 0.1646(4) 0.1325(4) 0.2749(9) 0.049(2) Uiso 0.5 1 d . . P
H23 H 0.1695 0.1025 0.2175 0.059 Uiso 0.5 1 calc R U P
C24 C 0.1363(4) 0.1180(5) 0.4055(10) 0.059(3) Uiso 0.5 1 d . . P
H24 H 0.1078 0.0767 0.4273 0.071 Uiso 0.5 1 calc R U P
C25 C 0.1496(4) 0.1632(4) 0.5024(10) 0.053(2) Uiso 0.5 1 d . . P
C26 C 0.1919(3) 0.2225(3) 0.4618(8) 0.033(2) Uiso 0.5 1 d . . P
H26 H 0.2010 0.2537 0.5274 0.040 Uiso 0.5 1 calc R U P
C27 C 0.2148(3) 0.2366(3) 0.3669(6) 0.0822(17) Uiso 1 1 d . . .
H27 H 0.2478 0.2773 0.3608 0.099 Uiso 1 1 calc R U .
C28 C 0.1183(5) 0.1477(5) 0.6421(11) 0.080(3) Uiso 0.5 1 d . . P
H28A H 0.1483 0.1555 0.7141 0.121 Uiso 0.5 1 calc R U P
H28B H 0.0866 0.1047 0.6438 0.121 Uiso 0.5 1 calc R U P
H28C H 0.0997 0.1731 0.6583 0.121 Uiso 0.5 1 calc R U P
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'
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
C1 C1 C16 130.77(18) 6 .
C1 C1 C2 93.07(18) 6 .
C16 C1 C2 136.1(3) . .
C3 C2 C1 132.7(3) . .
C3 C2 C2 140.4(2) . 6
C1 C2 C2 86.93(18) . 6
C2 C3 C10 125.9(3) . .
C2 C3 C4 119.1(3) . .
C10 C3 C4 115.0(3) . .
C5 C4 C9 118.6(3) . .
C5 C4 C3 120.8(3) . .
C9 C4 C3 120.6(3) . .
C6 C5 C4 120.6(3) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C7 C6 C5 120.3(3) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C8 119.6(3) . .
C6 C7 H7 120.2 . .
C8 C7 H7 120.2 . .
C9 C8 C7 120.5(3) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.7 . .
C8 C9 C4 120.3(3) . .
C8 C9 H9 119.8 . .
C4 C9 H9 119.8 . .
C15 C10 C11 117.8(3) . .
C15 C10 C3 122.4(3) . .
C11 C10 C3 119.7(3) . .
C12 C11 C10 121.6(3) . .
C12 C11 H11 119.2 . .
C10 C11 H11 119.2 . .
C13 C12 C11 119.4(3) . .
C13 C12 H12 120.3 . .
C11 C12 H12 120.3 . .
C14 C13 C12 120.3(3) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C13 C14 C15 120.1(3) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C14 C15 C10 120.7(3) . .
C14 C15 H15 119.6 . .
C10 C15 H15 119.6 . .
C21 C16 C17 118.3(3) . .
C21 C16 C1 120.0(3) . .
C17 C16 C1 121.6(3) . .
C18 C17 C16 120.3(3) . .
C18 C17 H17 119.8 . .
C16 C17 H17 119.8 . .
C19 C18 C17 120.2(3) . .
C19 C18 H18 119.9 . .
C17 C18 H18 119.9 . .
C20 C19 C18 120.2(3) . .
C20 C19 H19 119.9 . .
C18 C19 H19 119.9 . .
C19 C20 C21 120.0(3) . .
C19 C20 H20 120.0 . .
C21 C20 H20 120.0 . .
C20 C21 C16 121.0(3) . .
C20 C21 H21 119.5 . .
C16 C21 H21 119.5 . .
C27 C22 C27 125.4(8) . 6
C27 C22 C23 111.7(5) . 6
C27 C22 C23 115.4(5) 6 6
C27 C22 C23 115.4(5) . .
C27 C22 C23 111.7(5) 6 .
C23 C22 C23 58.9(7) 6 .
C24 C23 C23 95.2(9) . 6
C24 C23 C22 112.3(7) . .
C23 C23 C22 60.5(4) 6 .
C24 C23 H23 122.9 . .
C23 C23 H23 122.9 6 .
C22 C23 H23 122.9 . .
C25 C24 C23 120.8(9) . .
C25 C24 H24 119.6 . .
C23 C24 H24 119.6 . .
C24 C25 C26 115.8(9) . .
C24 C25 C28 120.8(9) . .
C26 C25 C28 123.4(9) . .
C27 C26 C25 127.6(9) . .
C27 C26 H26 116.2 . .
C25 C26 H26 116.2 . .
C26 C27 C22 125.2(8) . .
C26 C27 H27 117.4 . .
C22 C27 H27 117.4 . .
C25 C28 H28A 109.5 . .
C25 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C25 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C1 1.370(6) 6
C1 C16 1.473(5) .
C1 C2 1.493(5) .
C2 C3 1.355(5) .
C2 C2 1.530(7) 6
C3 C10 1.485(5) .
C3 C4 1.494(5) .
C4 C5 1.396(5) .
C4 C9 1.402(5) .
C5 C6 1.390(5) .
C5 H5 0.9500 .
C6 C7 1.382(5) .
C6 H6 0.9500 .
C7 C8 1.387(5) .
C7 H7 0.9500 .
C8 C9 1.386(5) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C15 1.397(5) .
C10 C11 1.399(5) .
C11 C12 1.384(5) .
C11 H11 0.9500 .
C12 C13 1.383(5) .
C12 H12 0.9500 .
C13 C14 1.383(5) .
C13 H13 0.9500 .
C14 C15 1.390(5) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C21 1.394(5) .
C16 C17 1.403(5) .
C17 C18 1.388(5) .
C17 H17 0.9500 .
C18 C19 1.380(5) .
C18 H18 0.9500 .
C19 C20 1.380(5) .
C19 H19 0.9500 .
C20 C21 1.384(5) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 C27 1.390(7) .
C22 C27 1.390(7) 6
C22 C23 1.512(11) 6
C22 C23 1.512(11) .
C23 C24 1.416(12) .
C23 C23 1.488(17) 6
C23 H23 1.0000 .
C24 C25 1.390(13) .
C24 H24 0.9500 .
C25 C26 1.396(12) .
C25 C28 1.524(14) .
C26 C27 1.054(8) .
C26 H26 0.9500 .
C27 H27 0.9500 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
