#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/65/7116553.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_7116553
loop_
_publ_author_name
'Arun Naibi Lakshminarayana'
'Jingjing Chang'
'Jie Luo'
'Bin Zheng'
'Kuo-Wei Huang'
'Chunyan Chi'
_publ_section_title
;
 Bisindeno-annulated pentacenes with exceptionally high photo-stability
 and ordered molecular packing: simple synthesis by a regio-selective
 Scholl reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              3604
_journal_paper_doi               10.1039/C4cc09812A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C43 H34 O1.5'
_chemical_formula_weight         574.70
_chemical_name_common            'di-tert butyl rubicenoid Pentacene'
_chemical_name_systematic        'di-tert butyl bisindenofused  pentacene'
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2014-11-20 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.7790(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.2227(14)
_cell_length_b                   16.4194(8)
_cell_length_c                   6.9476(4)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.61
_cell_volume                     3040.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            35647
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.481
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6662
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Dark_Green
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0549
_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)+(0.0767P)²+4.6491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2243
_reflns_number_total             2694
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4cc09812a2.cif
_cod_data_source_block           e411
_cod_original_formula_sum        'C43 H34 O1.50'
_cod_database_code               7116553
#BEGIN Tags that were not found in dictionaries:
_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           2014-3
#END Tags that were not found in dictionaries
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
O1S O 0.4555(2) 0.0867(4) 0.6028(8) 0.1063(18) Uani 0.5 1 d D U P A -1
C1S C 0.4793(4) 0.0294(7) 0.4813(18) 0.146(4) Uani 0.5 1 d D U P A -1
O1W O 0.5000 0.0325(9) 0.7500 0.179(5) Uani 0.5 2 d S TU P B 2
C19 C 0.67533(13) 0.15824(19) 0.2847(5) 0.0456(7) Uani 0.733(3) 1 d . U P C 1
H19A H 0.7015 0.1169 0.2896 0.068 Uiso 0.733(3) 1 calc R U P C 1
H19B H 0.6899 0.2125 0.2789 0.068 Uiso 0.733(3) 1 calc R U P C 1
H19C H 0.6489 0.1495 0.1676 0.068 Uiso 0.733(3) 1 calc R U P C 1
C20 C 0.69168(13) 0.1572(2) 0.6526(5) 0.0452(8) Uani 0.733(3) 1 d . U P C 1
H20A H 0.7177 0.1161 0.6511 0.068 Uiso 0.733(3) 1 calc R U P C 1
H20B H 0.6760 0.1478 0.7656 0.068 Uiso 0.733(3) 1 calc R U P C 1
H20C H 0.7069 0.2116 0.6629 0.068 Uiso 0.733(3) 1 calc R U P C 1
C21 C 0.62928(12) 0.06314(18) 0.4611(5) 0.0428(7) Uani 0.733(3) 1 d . U P C 1
H21A H 0.6028 0.0578 0.3429 0.064 Uiso 0.733(3) 1 calc R U P C 1
H21B H 0.6150 0.0547 0.5781 0.064 Uiso 0.733(3) 1 calc R U P C 1
H21C H 0.6554 0.0224 0.4579 0.064 Uiso 0.733(3) 1 calc R U P C 1
C19A C 0.7106(3) 0.1960(5) 0.4724(14) 0.0439(12) Uani 0.267(3) 1 d . U P C 2
H19D H 0.7360 0.1534 0.4765 0.066 Uiso 0.267(3) 1 calc R U P C 2
H19E H 0.7196 0.2306 0.5892 0.066 Uiso 0.267(3) 1 calc R U P C 2
H19F H 0.7089 0.2292 0.3540 0.066 Uiso 0.267(3) 1 calc R U P C 2
C20A C 0.6627(4) 0.1134(6) 0.6719(14) 0.0461(12) Uani 0.267(3) 1 d . U P C 2
H20D H 0.6326 0.0843 0.6906 0.069 Uiso 0.267(3) 1 calc R U P C 2
H20E H 0.6710 0.1561 0.7716 0.069 Uiso 0.267(3) 1 calc R U P C 2
H20F H 0.6908 0.0750 0.6848 0.069 Uiso 0.267(3) 1 calc R U P C 2
C21A C 0.6430(4) 0.1052(5) 0.3053(14) 0.0466(12) Uani 0.267(3) 1 d . U P C 2
H21D H 0.6702 0.0659 0.3081 0.070 Uiso 0.267(3) 1 calc R U P C 2
H21E H 0.6401 0.1400 0.1888 0.070 Uiso 0.267(3) 1 calc R U P C 2
H21F H 0.6114 0.0760 0.3004 0.070 Uiso 0.267(3) 1 calc R U P C 2
C1 C 0.62224(7) 0.59257(12) 0.4642(2) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.66100(7) 0.65021(13) 0.4559(3) 0.0295(5) Uani 1 1 d . . . . .
H2 H 0.6539 0.7067 0.4603 0.035 Uiso 1 1 calc R U . . .
C3 C 0.70789(7) 0.62601(14) 0.4417(3) 0.0333(5) Uani 1 1 d . . . . .
H3 H 0.7333 0.6654 0.4381 0.040 Uiso 1 1 calc R U . . .
C4 C 0.71881(7) 0.54197(13) 0.4323(3) 0.0317(5) Uani 1 1 d . . . . .
H4 H 0.7516 0.5255 0.4219 0.038 Uiso 1 1 calc R U . . .
C5 C 0.68339(7) 0.48456(13) 0.4380(3) 0.0266(5) Uani 1 1 d . . . . .
H5 H 0.6917 0.4286 0.4302 0.032 Uiso 1 1 calc R U . . .
C6 C 0.63357(6) 0.50668(12) 0.4557(2) 0.0219(4) Uani 1 1 d . . . . .
C7 C 0.59524(7) 0.45123(11) 0.4660(2) 0.0207(4) Uani 1 1 d . . . . .
C8 C 0.54743(6) 0.48095(11) 0.4831(2) 0.0190(4) Uani 1 1 d . . . . .
C9 C 0.53566(6) 0.56545(11) 0.4900(2) 0.0191(4) Uani 1 1 d . . . . .
C10 C 0.57464(7) 0.62015(12) 0.4798(2) 0.0222(4) Uani 1 1 d . . . . .
H10 H 0.5686 0.6770 0.4837 0.027 Uiso 1 1 calc R U . . .
C11 C 0.51402(6) 0.41634(11) 0.4924(2) 0.0194(4) Uani 1 1 d . . . . .
C12 C 0.54190(7) 0.34072(11) 0.4828(2) 0.0222(4) Uani 1 1 d . . . . .
C13 C 0.52865(7) 0.25957(12) 0.4875(3) 0.0284(5) Uani 1 1 d . . . . .
H13 H 0.4954 0.2451 0.4962 0.034 Uiso 1 1 calc R U . . .
C14 C 0.56391(8) 0.19928(13) 0.4794(3) 0.0334(5) Uani 1 1 d . . . . .
H14 H 0.5543 0.1437 0.4826 0.040 Uiso 1 1 calc R U . . .
C15 C 0.61324(8) 0.21840(13) 0.4666(3) 0.0315(5) Uani 1 1 d . . . . .
C16 C 0.62640(7) 0.30025(12) 0.4596(3) 0.0277(5) Uani 1 1 d . . . . .
H16 H 0.6596 0.3143 0.4496 0.033 Uiso 1 1 calc R U . . .
C17 C 0.59164(7) 0.36182(11) 0.4670(2) 0.0220(4) Uani 1 1 d . . . . .
C18 C 0.65303(9) 0.15160(13) 0.4679(3) 0.0386(6) Uani 1 1 d . . . . .
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
C10 C1 C2 119.54(18) . .
C10 C1 C6 121.84(17) . .
C2 C1 C6 118.62(17) . .
C3 C2 C1 121.5(2) . .
C2 C3 C4 119.82(19) . .
C5 C4 C3 121.29(18) . .
C4 C5 C6 121.18(19) . .
C7 C6 C5 124.67(18) . .
C7 C6 C1 117.71(16) . .
C5 C6 C1 117.63(17) . .
C6 C7 C8 119.21(17) . .
C6 C7 C17 134.52(16) . .
C8 C7 C17 106.26(16) . .
C11 C8 C7 110.95(16) . .
C11 C8 C9 125.43(16) . .
C7 C8 C9 123.63(17) . .
C10 C9 C11 127.98(17) . 5_666
C10 C9 C8 116.33(16) . .
C11 C9 C8 115.69(17) 5_666 .
C1 C10 C9 121.28(17) . .
C8 C11 C9 118.88(16) . 5_666
C8 C11 C12 106.94(15) . .
C9 C11 C12 134.18(17) 5_666 .
C13 C12 C17 119.55(17) . .
C13 C12 C11 132.56(17) . .
C17 C12 C11 107.89(16) . .
C12 C13 C14 120.04(19) . .
C13 C14 C15 121.5(2) . .
C16 C15 C14 118.37(17) . .
C16 C15 C18 120.08(19) . .
C14 C15 C18 121.51(19) . .
C17 C16 C15 121.13(19) . .
C16 C17 C12 119.36(18) . .
C16 C17 C7 132.66(18) . .
C12 C17 C7 107.96(15) . .
C20 C18 C19 112.6(3) . .
C21A C18 C20A 121.0(6) . .
C21A C18 C15 112.1(4) . .
C20 C18 C15 109.5(2) . .
C19 C18 C15 110.13(19) . .
C20A C18 C15 106.7(3) . .
C20 C18 C21 107.2(2) . .
C19 C18 C21 105.7(2) . .
C15 C18 C21 111.7(2) . .
C21A C18 C19A 106.4(5) . .
C20A C18 C19A 100.0(5) . .
C15 C18 C19A 109.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1S C1S 1.498(11) .
C19 C18 1.522(4) .
C20 C18 1.487(4) .
C21 C18 1.587(4) .
C19A C18 1.723(9) .
C20A C18 1.523(9) .
C21A C18 1.343(9) .
C1 C10 1.398(3) .
C1 C2 1.427(3) .
C1 C6 1.447(3) .
C2 C3 1.360(3) .
C3 C4 1.416(3) .
C4 C5 1.355(3) .
C5 C6 1.433(2) .
C6 C7 1.398(3) .
C7 C8 1.417(2) .
C7 C17 1.471(3) .
C8 C11 1.407(3) .
C8 C9 1.427(2) .
C9 C10 1.403(3) .
C9 C11 1.415(2) 5_666
C11 C9 1.415(2) 5_666
C11 C12 1.464(2) .
C12 C13 1.383(3) .
C12 C17 1.424(3) .
C13 C14 1.388(3) .
C14 C15 1.400(3) .
C15 C16 1.394(3) .
C15 C18 1.540(3) .
C16 C17 1.393(3) .
