#------------------------------------------------------------------------------
#$Date: 2019-06-01 05:49:56 +0200 (Sat 01 de Jun de 2019) $
#$Revision: 215648 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/28/7232854.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_7232854
loop_
_publ_author_name
'Tajima, Tomoyuki'
'Sanda, Rai'
'Nishihara, Katsuya'
'Shirai, Hitoshi'
'Okuda, Yasuhiro'
'Orita, Akihiro'
'Takaguchi, Yutaka'
_publ_section_title
;
 Disproportionation-induced solid-state fluorescence in
 6,13-dihydropentacenes
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              17035
_journal_paper_doi               10.1039/C9RA03297E
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C52 H66 N2 O4'
_chemical_formula_weight         783.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc22587s
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-23 deposited with the CCDC.    2019-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                91.765(12)
_cell_angle_beta                 91.622(12)
_cell_angle_gamma                92.166(15)
_cell_formula_units_Z            1
_cell_length_a                   4.638(3)
_cell_length_b                   9.316(5)
_cell_length_c                   24.909(14)
_cell_measurement_reflns_used    3149
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      29.6
_cell_measurement_theta_min      2.5
_cell_volume                     1074.5(11)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Rigaku/Saturn70 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7750
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.490
_diffrn_reflns_theta_min         2.361
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0491
_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)+(0.0609P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2680
_reflns_number_total             4205
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra03297e2.cif
_cod_data_source_block           3b
_cod_database_code               7232854
_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   0.978
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 1.2044(4) 0.12307(18) 0.65064(7) 0.0178(4) Uani 1 1 d . .
C2 C 1.0087(4) 0.22872(18) 0.65161(7) 0.0191(4) Uani 1 1 d . .
H2 H 0.9414 0.2659 0.6847 0.023 Uiso 1 1 calc R U
C3 C 0.9073(3) 0.28210(18) 0.60159(7) 0.0165(4) Uani 1 1 d . .
C4 C 0.7081(3) 0.39244(18) 0.59914(7) 0.0172(4) Uani 1 1 d . .
H4 H 0.6409 0.4328 0.6317 0.021 Uiso 1 1 calc R U
C5 C 0.6073(3) 0.44391(18) 0.55101(7) 0.0157(4) Uani 1 1 d . .
C6 C 0.3976(3) 0.56398(18) 0.55181(7) 0.0174(4) Uani 1 1 d . .
H6 H 0.2264 0.5317 0.5717 0.021 Uiso 1 1 calc R U
H6A H 0.4897 0.6470 0.5723 0.021 Uiso 1 1 calc R U
C7 C 0.2951(3) 0.61538(18) 0.49803(7) 0.0160(4) Uani 1 1 d . .
C8 C 0.0976(3) 0.72362(18) 0.49683(7) 0.0166(4) Uani 1 1 d . .
H8 H 0.0322 0.7628 0.5298 0.020 Uiso 1 1 calc R U
C9 C -0.0086(3) 0.77705(18) 0.44793(7) 0.0168(4) Uani 1 1 d . .
C10 C -0.2162(3) 0.88714(18) 0.44699(7) 0.0175(4) Uani 1 1 d . .
H10 H -0.2872 0.9268 0.4794 0.021 Uiso 1 1 calc R U
C11 C -0.3085(3) 0.93323(18) 0.39849(7) 0.0168(4) Uani 1 1 d . .
C12 C -0.5194(4) 1.04400(18) 0.38471(7) 0.0182(4) Uani 1 1 d . .
O1 O -0.6652(2) 1.11597(13) 0.41448(5) 0.0229(3) Uani 1 1 d . .
N1 N -0.5231(3) 1.05170(15) 0.32879(6) 0.0193(3) Uani 1 1 d . .
C13 C -0.3431(4) 0.95185(19) 0.30421(8) 0.0202(4) Uani 1 1 d . .
O2 O -0.3147(3) 0.93690(14) 0.25619(5) 0.0263(3) Uani 1 1 d . .
C14 C -0.6977(4) 1.15098(19) 0.29823(8) 0.0220(4) Uani 1 1 d . .
H14 H -0.8627 1.1799 0.3199 0.026 Uiso 1 1 calc R U
H14A H -0.7763 1.1010 0.2650 0.026 Uiso 1 1 calc R U
C15 C -0.5227(4) 1.28491(19) 0.28333(7) 0.0213(4) Uani 1 1 d . .
H15 H -0.3609 1.2559 0.2608 0.026 Uiso 1 1 calc R U
H15A H -0.4393 1.3330 0.3165 0.026 Uiso 1 1 calc R U
C16 C -0.7035(4) 1.39169(19) 0.25280(7) 0.0212(4) Uani 1 1 d . .
H16 H -0.7925 1.3426 0.2203 0.025 Uiso 1 1 calc R U
H16A H -0.8612 1.4233 0.2758 0.025 Uiso 1 1 calc R U
C17 C -0.5266(4) 1.52335(19) 0.23616(8) 0.0226(4) Uani 1 1 d . .
H17 H -0.3676 1.4908 0.2136 0.027 Uiso 1 1 calc R U
H17A H -0.4384 1.5719 0.2689 0.027 Uiso 1 1 calc R U
C18 C -0.6979(4) 1.63323(19) 0.20500(7) 0.0232(4) Uani 1 1 d . .
H18 H -0.8721 1.6556 0.2253 0.028 Uiso 1 1 calc R U
H18A H -0.5781 1.7231 0.2033 0.028 Uiso 1 1 calc R U
C19 C -0.7916(4) 1.5848(2) 0.14801(7) 0.0234(4) Uani 1 1 d . .
H19 H -0.9165 1.4965 0.1494 0.028 Uiso 1 1 calc R U
H19A H -0.6187 1.5607 0.1277 0.028 Uiso 1 1 calc R U
C20 C -0.9551(4) 1.6988(2) 0.11826(8) 0.0242(4) Uani 1 1 d . .
H20 H -0.8305 1.7873 0.1174 0.029 Uiso 1 1 calc R U
H20A H -1.1283 1.7222 0.1387 0.029 Uiso 1 1 calc R U
C21 C -1.0498(4) 1.65384(19) 0.06077(7) 0.0248(4) Uani 1 1 d . .
H21 H -0.8766 1.6319 0.0402 0.030 Uiso 1 1 calc R U
H21A H -1.1723 1.5646 0.0615 0.030 Uiso 1 1 calc R U
C22 C -1.2168(4) 1.7677(2) 0.03172(7) 0.0237(4) Uani 1 1 d . .
H22 H -1.0935 1.8566 0.0306 0.028 Uiso 1 1 calc R U
H22A H -1.3889 1.7903 0.0525 0.028 Uiso 1 1 calc R U
C23 C -1.3142(4) 1.7221(2) -0.02565(8) 0.0260(5) Uani 1 1 d . .
H23 H -1.1417 1.7009 -0.0466 0.031 Uiso 1 1 calc R U
H23A H -1.4348 1.6324 -0.0246 0.031 Uiso 1 1 calc R U
C24 C -1.4850(4) 1.8347(2) -0.05454(7) 0.0254(4) Uani 1 1 d . .
H24 H -1.3628 1.9239 -0.0562 0.030 Uiso 1 1 calc R U
H24A H -1.6552 1.8573 -0.0332 0.030 Uiso 1 1 calc R U
C25 C -1.5875(4) 1.7888(2) -0.11140(8) 0.0286(5) Uani 1 1 d . .
H25 H -1.4178 1.7665 -0.1329 0.034 Uiso 1 1 calc R U
H25A H -1.7104 1.6999 -0.1099 0.034 Uiso 1 1 calc R U
C26 C -1.7578(5) 1.9033(2) -0.13934(8) 0.0366(5) Uani 1 1 d . .
H26 H -1.9276 1.9251 -0.1185 0.055 Uiso 1 1 calc R U
H26A H -1.8198 1.8678 -0.1754 0.055 Uiso 1 1 calc R U
H26B H -1.6353 1.9907 -0.1421 0.055 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 0.0033 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'
N N 0.0061 0.0033 '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
C2 C1 C11 121.56(16) . 2_666
C2 C1 C13 129.78(17) . 2_666
C11 C1 C13 108.66(15) 2_666 2_666
C1 C2 C3 118.36(17) . .
C4 C3 C2 121.87(16) . .
C4 C3 C9 118.23(16) . 2_666
C2 C3 C9 119.90(16) . 2_666
C5 C4 C3 122.29(17) . .
C4 C5 C7 119.58(16) . 2_666
C4 C5 C6 119.07(16) . .
C7 C5 C6 121.34(15) 2_666 .
C7 C6 C5 116.59(15) . .
C8 C7 C5 119.38(16) . 2_666
C8 C7 C6 118.56(16) . .
C5 C7 C6 122.07(15) 2_666 .
C7 C8 C9 121.74(17) . .
C8 C9 C10 121.42(16) . .
C8 C9 C3 118.78(16) . 2_666
C10 C9 C3 119.80(16) . 2_666
C11 C10 C9 118.15(17) . .
C10 C11 C1 122.22(16) . 2_666
C10 C11 C12 130.53(17) . .
C1 C11 C12 107.25(15) 2_666 .
O1 C12 N1 124.69(16) . .
O1 C12 C11 129.16(17) . .
N1 C12 C11 106.15(14) . .
C12 N1 C13 112.77(14) . .
C12 N1 C14 124.20(14) . .
C13 N1 C14 123.02(15) . .
O2 C13 N1 124.78(16) . .
O2 C13 C1 130.11(17) . 2_666
N1 C13 C1 105.10(15) . 2_666
N1 C14 C15 111.98(15) . .
C14 C15 C16 112.70(15) . .
C17 C16 C15 112.80(15) . .
C16 C17 C18 114.79(15) . .
C19 C18 C17 114.81(15) . .
C18 C19 C20 112.87(15) . .
C19 C20 C21 114.11(15) . .
C22 C21 C20 113.65(15) . .
C21 C22 C23 113.68(15) . .
C24 C23 C22 113.85(15) . .
C23 C24 C25 114.09(15) . .
C26 C25 C24 112.98(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.364(2) .
C1 C11 1.421(2) 2_666
C1 C13 1.486(2) 2_666
C2 C3 1.430(2) .
C3 C4 1.409(2) .
C3 C9 1.434(2) 2_666
C4 C5 1.381(2) .
C5 C7 1.418(2) 2_666
C5 C6 1.510(2) .
C6 C7 1.507(2) .
C7 C8 1.388(2) .
C7 C5 1.418(2) 2_666
C8 C9 1.413(2) .
C9 C10 1.433(2) .
C9 C3 1.434(2) 2_666
C10 C11 1.358(2) .
C11 C1 1.421(2) 2_666
C11 C12 1.489(2) .
C12 O1 1.220(2) .
C12 N1 1.397(2) .
N1 C13 1.411(2) .
N1 C14 1.468(2) .
C13 O2 1.212(2) .
C13 C1 1.486(2) 2_666
C14 C15 1.524(2) .
C15 C16 1.531(2) .
C16 C17 1.524(2) .
C17 C18 1.535(2) .
C18 C19 1.522(3) .
C19 C20 1.526(2) .
C20 C21 1.527(3) .
C21 C22 1.525(2) .
C22 C23 1.529(3) .
C23 C24 1.524(2) .
C24 C25 1.525(3) .
C25 C26 1.525(3) .
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
C11 C1 C2 C3 0.3(3) 2_666 .
C13 C1 C2 C3 -179.61(16) 2_666 .
C1 C2 C3 C4 -179.14(15) . .
C1 C2 C3 C9 0.9(2) . 2_666
C2 C3 C4 C5 -179.48(15) . .
C9 C3 C4 C5 0.5(3) 2_666 .
C3 C4 C5 C7 0.1(3) . 2_666
C3 C4 C5 C6 -179.04(15) . .
C4 C5 C6 C7 -179.92(14) . .
C7 C5 C6 C7 0.9(3) 2_666 .
C5 C6 C7 C8 178.72(14) . .
C5 C6 C7 C5 -0.9(3) . 2_666
C5 C7 C8 C9 -0.2(3) 2_666 .
C6 C7 C8 C9 -179.88(14) . .
C7 C8 C9 C10 178.92(15) . .
C7 C8 C9 C3 -0.4(3) . 2_666
C8 C9 C10 C11 180.00(15) . .
C3 C9 C10 C11 -0.7(2) 2_666 .
C9 C10 C11 C1 -0.6(3) . 2_666
C9 C10 C11 C12 179.90(16) . .
C10 C11 C12 O1 -2.6(3) . .
C1 C11 C12 O1 177.81(17) 2_666 .
C10 C11 C12 N1 177.62(17) . .
C1 C11 C12 N1 -1.98(18) 2_666 .
O1 C12 N1 C13 -177.28(16) . .
C11 C12 N1 C13 2.52(19) . .
O1 C12 N1 C14 1.9(3) . .
C11 C12 N1 C14 -178.33(14) . .
C12 N1 C13 O2 178.77(17) . .
C14 N1 C13 O2 -0.4(3) . .
C12 N1 C13 C1 -2.02(19) . 2_666
C14 N1 C13 C1 178.82(14) . 2_666
C12 N1 C14 C15 98.07(19) . .
C13 N1 C14 C15 -82.9(2) . .
N1 C14 C15 C16 -178.38(14) . .
C14 C15 C16 C17 -178.01(16) . .
C15 C16 C17 C18 179.55(15) . .
C16 C17 C18 C19 -71.1(2) . .
C17 C18 C19 C20 -178.70(15) . .
C18 C19 C20 C21 179.49(15) . .
C19 C20 C21 C22 179.15(15) . .
C20 C21 C22 C23 -179.43(16) . .
C21 C22 C23 C24 179.14(15) . .
C22 C23 C24 C25 -178.91(16) . .
C23 C24 C25 C26 179.98(16) . .
