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#$Date: 2025-08-19 21:30:04 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301811 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/07/4000785.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_4000785
loop_
_publ_author_name
'Fumagalli, Enrico'
'Raimondo, Luisa'
'Silvestri, Leonardo'
'Moret, Massimo'
'Sassella, Adele'
'Campione, Marcello'
_publ_section_title
;
 Oxidation Dynamics of Epitaxial Rubrene Ultrathin Films
;
_journal_issue                   13
_journal_name_full               'Chemistry of Materials'
_journal_page_first              3246
_journal_paper_doi               10.1021/cm201230j
_journal_volume                  23
_journal_year                    2011
_chemical_formula_moiety         'C42 H28 O2, 2(C4 H8 O2)'
_chemical_formula_sum            'C50 H44 O6'
_chemical_formula_weight         740.85
_chemical_name_common            'rubrene endoperoxide dioxane solvate'
_chemical_name_systematic
'5,6,11,12-tetraphenyl-5,6-epidioxytetracene dioxane solvate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.7030(10)
_cell_angle_beta                 94.3070(10)
_cell_angle_gamma                97.8670(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6249(6)
_cell_length_b                   11.1636(9)
_cell_length_c                   22.6554(19)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      45.3
_cell_measurement_theta_min      6.2
_cell_volume                     1860.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury 2.3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al, 2002)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24302
_diffrn_reflns_theta_full        29.48
_diffrn_reflns_theta_max         29.48
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         9505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.5766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                7086
_reflns_number_total             9505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm201230j_si_002.cif
_cod_data_source_block           max28
_cod_database_code               4000785
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.80977(13) 0.30743(9) 0.30407(5) 0.0230(2) Uani 1 1 d .
O2 O 0.71631(13) 0.41499(9) 0.31439(5) 0.0240(2) Uani 1 1 d .
C1 C 0.39980(19) 0.31853(14) 0.40741(6) 0.0249(3) Uani 1 1 d .
H1 H 0.3447 0.3905 0.4163 0.030 Uiso 1 1 calc R
C2 C 0.3897(2) 0.23516(15) 0.44542(7) 0.0284(3) Uani 1 1 d .
H2 H 0.3240 0.2488 0.4795 0.034 Uiso 1 1 calc R
C3 C 0.4744(2) 0.13282(14) 0.43389(7) 0.0268(3) Uani 1 1 d .
H3 H 0.4664 0.0760 0.4600 0.032 Uiso 1 1 calc R
C4 C 0.57188(19) 0.11219(13) 0.38420(6) 0.0232(3) Uani 1 1 d .
H4 H 0.6340 0.0433 0.3772 0.028 Uiso 1 1 calc R
C5 C 0.57734(18) 0.19333(12) 0.34496(6) 0.0199(3) Uani 1 1 d .
C6 C 0.68597(18) 0.18994(12) 0.29089(6) 0.0192(3) Uani 1 1 d .
C7 C 0.56236(17) 0.19530(12) 0.23488(6) 0.0182(3) Uani 1 1 d .
C8 C 0.54441(18) 0.11913(12) 0.17778(6) 0.0187(3) Uani 1 1 d .
C9 C 0.41706(17) 0.13797(12) 0.13166(6) 0.0191(3) Uani 1 1 d .
C10 C 0.38812(19) 0.06046(13) 0.07253(6) 0.0229(3) Uani 1 1 d .
H10 H 0.4534 -0.0064 0.0633 0.028 Uiso 1 1 calc R
C11 C 0.2686(2) 0.07985(14) 0.02872(7) 0.0258(3) Uani 1 1 d .
H11 H 0.2502 0.0258 -0.0102 0.031 Uiso 1 1 calc R
C12 C 0.1732(2) 0.17910(14) 0.04101(7) 0.0263(3) Uani 1 1 d .
H12 H 0.0901 0.1924 0.0105 0.032 Uiso 1 1 calc R
C13 C 0.20004(19) 0.25694(13) 0.09699(6) 0.0236(3) Uani 1 1 d .
H13 H 0.1363 0.3249 0.1046 0.028 Uiso 1 1 calc R
C14 C 0.32061(18) 0.23870(12) 0.14390(6) 0.0197(3) Uani 1 1 d .
C15 C 0.35275(18) 0.32332(12) 0.20217(6) 0.0196(3) Uani 1 1 d .
C16 C 0.46743(17) 0.30015(12) 0.24673(6) 0.0185(3) Uani 1 1 d .
C17 C 0.52239(18) 0.37960(12) 0.31125(6) 0.0200(3) Uani 1 1 d .
C18 C 0.49059(18) 0.29642(12) 0.35643(6) 0.0200(3) Uani 1 1 d .
C19 C 0.80937(18) 0.09357(13) 0.28860(6) 0.0213(3) Uani 1 1 d .
C20 C 0.7388(2) -0.03140(13) 0.27966(6) 0.0244(3) Uani 1 1 d .
H20 H 0.6136 -0.0566 0.2718 0.029 Uiso 1 1 calc R
C21 C 0.8495(2) -0.11911(15) 0.28205(7) 0.0301(3) Uani 1 1 d .
H21 H 0.8003 -0.2042 0.2754 0.036 Uiso 1 1 calc R
C22 C 1.0317(2) -0.08306(16) 0.29412(7) 0.0348(4) Uani 1 1 d .
H22 H 1.1077 -0.1432 0.2962 0.042 Uiso 1 1 calc R
C23 C 1.1024(2) 0.04000(16) 0.30316(8) 0.0362(4) Uani 1 1 d .
H23 H 1.2276 0.0647 0.3113 0.043 Uiso 1 1 calc R
C24 C 0.9927(2) 0.12836(15) 0.30053(7) 0.0285(3) Uani 1 1 d .
H24 H 1.0431 0.2132 0.3069 0.034 Uiso 1 1 calc R
C25 C 0.65654(18) 0.02121(12) 0.15849(6) 0.0196(3) Uani 1 1 d .
C26 C 0.5842(2) -0.10410(13) 0.14370(7) 0.0249(3) Uani 1 1 d .
H26 H 0.4613 -0.1286 0.1465 0.030 Uiso 1 1 calc R
C27 C 0.6902(2) -0.19340(14) 0.12489(7) 0.0298(3) Uani 1 1 d .
H27 H 0.6403 -0.2787 0.1159 0.036 Uiso 1 1 calc R
C28 C 0.8683(2) -0.15836(15) 0.11926(7) 0.0303(3) Uani 1 1 d .
H28 H 0.9408 -0.2195 0.1065 0.036 Uiso 1 1 calc R
C29 C 0.9404(2) -0.03453(15) 0.13215(7) 0.0285(3) Uani 1 1 d .
H29 H 1.0624 -0.0104 0.1278 0.034 Uiso 1 1 calc R
C30 C 0.83491(19) 0.05497(13) 0.15144(6) 0.0231(3) Uani 1 1 d .
H30 H 0.8852 0.1401 0.1599 0.028 Uiso 1 1 calc R
C31 C 0.2588(2) 0.43349(13) 0.20719(6) 0.0226(3) Uani 1 1 d .
C32 C 0.3465(3) 0.54598(14) 0.19992(7) 0.0332(4) Uani 1 1 d .
H32 H 0.4701 0.5562 0.1953 0.040 Uiso 1 1 calc R
C33 C 0.2512(3) 0.64413(16) 0.19943(8) 0.0482(5) Uani 1 1 d .
H33 H 0.3108 0.7218 0.1950 0.058 Uiso 1 1 calc R
C34 C 0.0706(3) 0.62906(19) 0.20539(8) 0.0504(6) Uani 1 1 d .
H34 H 0.0062 0.6957 0.2039 0.061 Uiso 1 1 calc R
C35 C -0.0152(3) 0.51887(18) 0.21332(8) 0.0425(5) Uani 1 1 d .
H35 H -0.1385 0.5094 0.2184 0.051 Uiso 1 1 calc R
C36 C 0.0774(2) 0.42092(15) 0.21401(7) 0.0306(3) Uani 1 1 d .
H36 H 0.0167 0.3442 0.2192 0.037 Uiso 1 1 calc R
C37 C 0.45966(19) 0.50417(13) 0.33085(6) 0.0224(3) Uani 1 1 d .
C38 C 0.5794(2) 0.61420(13) 0.34411(7) 0.0282(3) Uani 1 1 d .
H38 H 0.7010 0.6125 0.3380 0.034 Uiso 1 1 calc R
C39 C 0.5233(2) 0.72654(14) 0.36618(8) 0.0347(4) Uani 1 1 d .
H39 H 0.6066 0.8010 0.3752 0.042 Uiso 1 1 calc R
C40 C 0.3468(2) 0.73025(15) 0.37507(7) 0.0347(4) Uani 1 1 d .
H40 H 0.3087 0.8071 0.3903 0.042 Uiso 1 1 calc R
C41 C 0.2258(2) 0.62193(15) 0.36171(7) 0.0309(3) Uani 1 1 d .
H41 H 0.1040 0.6244 0.3672 0.037 Uiso 1 1 calc R
C42 C 0.2821(2) 0.50964(13) 0.34022(6) 0.0251(3) Uani 1 1 d .
H42 H 0.1984 0.4354 0.3318 0.030 Uiso 1 1 calc R
O1S O 0.81533(17) 0.32009(12) -0.02145(7) 0.0467(3) Uani 1 1 d .
C2S C 0.7109(3) 0.27570(17) 0.02131(11) 0.0503(5) Uani 1 1 d .
H2S1 H 0.7581 0.2043 0.0328 0.060 Uiso 1 1 calc R
H2S2 H 0.5866 0.2470 0.0027 0.060 Uiso 1 1 calc R
C3S C 0.7138(3) 0.37505(18) 0.07655(9) 0.0438(4) Uani 1 1 d .
H3S1 H 0.6414 0.3421 0.1059 0.053 Uiso 1 1 calc R
H3S2 H 0.8376 0.4014 0.0960 0.053 Uiso 1 1 calc R
O4S O 0.64566(16) 0.47876(11) 0.06187(6) 0.0390(3) Uani 1 1 d .
C5S C 0.7466(2) 0.52361(16) 0.01840(9) 0.0391(4) Uani 1 1 d .
H5S1 H 0.8705 0.5552 0.0367 0.047 Uiso 1 1 calc R
H5S2 H 0.6953 0.5932 0.0065 0.047 Uiso 1 1 calc R
C6S C 0.7472(2) 0.42393(18) -0.03671(9) 0.0435(4) Uani 1 1 d .
H6S1 H 0.6243 0.3970 -0.0569 0.052 Uiso 1 1 calc R
H6S2 H 0.8212 0.4572 -0.0656 0.052 Uiso 1 1 calc R
O1T O 1.06298(17) 0.38695(10) 0.49835(6) 0.0405(3) Uani 1 1 d .
C2T C 0.8291(2) 0.49726(16) 0.47467(9) 0.0413(4) Uani 1 1 d .
H2T1 H 0.7475 0.5080 0.4407 0.050 Uiso 1 1 calc R
H2T2 H 0.7559 0.4693 0.5050 0.050 Uiso 1 1 calc R
C3T C 0.9390(2) 0.40160(16) 0.45176(8) 0.0390(4) Uani 1 1 d .
H3T1 H 0.8605 0.3217 0.4351 0.047 Uiso 1 1 calc R
H3T2 H 1.0035 0.4257 0.4186 0.047 Uiso 1 1 calc R
O1U O 0.82828(15) -0.02905(11) 0.46723(6) 0.0360(3) Uani 1 1 d .
C2U C 0.9576(2) -0.10925(16) 0.45677(8) 0.0359(4) Uani 1 1 d .
H2U1 H 1.0256 -0.0898 0.4235 0.043 Uiso 1 1 calc R
H2U2 H 0.8969 -0.1961 0.4442 0.043 Uiso 1 1 calc R
C3U C 0.9163(2) 0.09553(15) 0.48703(8) 0.0350(4) Uani 1 1 d .
H3U1 H 0.8268 0.1514 0.4956 0.042 Uiso 1 1 calc R
H3U2 H 0.9833 0.1198 0.4544 0.042 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
O2 O1 C6 112.06(9) . .
O1 O2 C17 112.52(9) . .
C18 C1 C2 119.84(13) . .
C3 C2 C1 120.31(14) . .
C2 C3 C4 120.37(14) . .
C5 C4 C3 119.40(13) . .
C4 C5 C18 120.16(13) . .
C4 C5 C6 126.54(12) . .
C18 C5 C6 113.05(12) . .
O1 C6 C19 103.12(10) . .
O1 C6 C5 106.02(10) . .
C19 C6 C5 111.04(11) . .
O1 C6 C7 104.95(10) . .
C19 C6 C7 121.52(11) . .
C5 C6 C7 108.80(11) . .
C8 C7 C16 120.61(12) . .
C8 C7 C6 127.78(12) . .
C16 C7 C6 111.49(11) . .
C7 C8 C9 119.07(12) . .
C7 C8 C25 124.60(12) . .
C9 C8 C25 116.23(11) . .
C14 C9 C10 118.09(12) . .
C14 C9 C8 119.98(12) . .
C10 C9 C8 121.89(12) . .
C11 C10 C9 121.58(13) . .
C10 C11 C12 120.17(13) . .
C13 C12 C11 119.88(13) . .
C12 C13 C14 121.62(13) . .
C13 C14 C9 118.64(12) . .
C13 C14 C15 121.40(12) . .
C9 C14 C15 119.90(12) . .
C16 C15 C14 119.30(12) . .
C16 C15 C31 125.81(12) . .
C14 C15 C31 114.85(11) . .
C15 C16 C7 120.80(12) . .
C15 C16 C17 127.47(12) . .
C7 C16 C17 111.62(11) . .
O2 C17 C37 102.49(10) . .
O2 C17 C18 106.37(10) . .
C37 C17 C18 112.64(11) . .
O2 C17 C16 104.75(10) . .
C37 C17 C16 120.88(11) . .
C18 C17 C16 108.30(11) . .
C1 C18 C5 119.83(13) . .
C1 C18 C17 127.23(12) . .
C5 C18 C17 112.74(12) . .
C24 C19 C20 118.68(13) . .
C24 C19 C6 121.06(13) . .
C20 C19 C6 120.02(12) . .
C21 C20 C19 120.54(14) . .
C22 C21 C20 120.13(15) . .
C23 C22 C21 119.70(14) . .
C22 C23 C24 120.59(15) . .
C23 C24 C19 120.36(15) . .
C30 C25 C26 118.57(13) . .
C30 C25 C8 119.79(12) . .
C26 C25 C8 121.53(12) . .
C27 C26 C25 120.57(14) . .
C28 C27 C26 120.09(14) . .
C29 C28 C27 119.92(14) . .
C28 C29 C30 120.09(14) . .
C29 C30 C25 120.71(14) . .
C32 C31 C36 119.27(14) . .
C32 C31 C15 120.58(13) . .
C36 C31 C15 119.92(13) . .
C31 C32 C33 119.31(17) . .
C34 C33 C32 120.46(18) . .
C35 C34 C33 120.20(16) . .
C34 C35 C36 119.98(18) . .
C35 C36 C31 120.76(16) . .
C38 C37 C42 118.26(13) . .
C38 C37 C17 121.14(13) . .
C42 C37 C17 120.43(13) . .
C39 C38 C37 120.81(15) . .
C40 C39 C38 120.14(15) . .
C39 C40 C41 119.81(14) . .
C40 C41 C42 120.05(15) . .
C41 C42 C37 120.92(14) . .
C2S O1S C6S 108.70(14) . .
O1S C2S C3S 110.68(15) . .
O4S C3S C2S 111.10(16) . .
C3S O4S C5S 109.29(13) . .
O4S C5S C6S 111.23(15) . .
O1S C6S C5S 111.27(15) . .
C3T O1T C2T 110.25(13) . 2_766
O1T C2T C3T 111.48(15) 2_766 .
O1T C3T C2T 111.21(14) . .
C2U O1U C3U 109.24(12) . .
O1U C2U C3U 111.03(14) . 2_756
O1U C3U C2U 110.83(13) . 2_756
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 O2 1.4662(13) .
O1 C6 1.4698(16) .
O2 C17 1.4698(16) .
C1 C18 1.388(2) .
C1 C2 1.389(2) .
C2 C3 1.378(2) .
C3 C4 1.393(2) .
C4 C5 1.3908(19) .
C5 C18 1.3937(18) .
C5 C6 1.5264(19) .
C6 C19 1.5190(18) .
C6 C7 1.5390(18) .
C7 C8 1.3823(18) .
C7 C16 1.4490(18) .
C8 C9 1.4394(19) .
C8 C25 1.4950(18) .
C9 C14 1.4188(18) .
C9 C10 1.4229(19) .
C10 C11 1.367(2) .
C11 C12 1.400(2) .
C12 C13 1.368(2) .
C13 C14 1.4173(19) .
C14 C15 1.4412(19) .
C15 C16 1.3732(19) .
C15 C31 1.4953(18) .
C16 C17 1.5425(18) .
C17 C37 1.5242(18) .
C17 C18 1.5267(19) .
C19 C24 1.389(2) .
C19 C20 1.393(2) .
C20 C21 1.384(2) .
C21 C22 1.383(2) .
C22 C23 1.373(2) .
C23 C24 1.385(2) .
C25 C30 1.391(2) .
C25 C26 1.3944(19) .
C26 C27 1.389(2) .
C27 C28 1.384(2) .
C28 C29 1.379(2) .
C29 C30 1.390(2) .
C31 C32 1.386(2) .
C31 C36 1.394(2) .
C32 C33 1.396(2) .
C33 C34 1.385(3) .
C34 C35 1.364(3) .
C35 C36 1.382(2) .
C37 C38 1.391(2) .
C37 C42 1.394(2) .
C38 C39 1.389(2) .
C39 C40 1.381(3) .
C40 C41 1.382(2) .
C41 C42 1.387(2) .
O1S C2S 1.421(2) .
O1S C6S 1.426(2) .
C2S C3S 1.491(3) .
C3S O4S 1.420(2) .
O4S C5S 1.421(2) .
C5S C6S 1.495(3) .
O1T C3T 1.413(2) .
O1T C2T 1.426(2) 2_766
C2T O1T 1.426(2) 2_766
C2T C3T 1.482(2) .
O1U C2U 1.422(2) .
O1U C3U 1.426(2) .
C2U C3U 1.505(2) 2_756
C3U C2U 1.505(2) 2_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139089125
