#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/37/2213793.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213793
loop_
_publ_author_name
'Schuck, Götz'
'Haas, Simon'
'Stassen, Arno F.'
'Kirner, Hans-Jörg'
'Batlogg, Bertram'
_publ_section_title
;
 5,12-Bis(4-tert-butylphenyl)-6,11-diphenylnaphthacene
;
_journal_coeditor_code           HB2400
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2893
_journal_page_last               o2893
_journal_paper_doi               10.1107/S1600536807022489
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C50 H44'
_chemical_formula_moiety         'C50 H44'
_chemical_formula_sum            'C50 H44'
_chemical_formula_weight         644.90
_chemical_name_common
5,12-bis-(4-tert-butyl-phenyl)-6,12-diphenyl-naphthacene
_chemical_name_systematic
;
5,12-Bis(4-tert-butyl-phenyl)-6,11-diphenylnaphthacene
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.158(2)
_cell_length_b                   35.390(5)
_cell_length_c                   7.2215(11)
_cell_measurement_reflns_used    3136
_cell_measurement_temperature    292.0(10)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      3.00
_cell_volume                     3618.3(9)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292.0(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28135
_diffrn_reflns_theta_full        25.56
_diffrn_reflns_theta_max         25.56
_diffrn_reflns_theta_min         1.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996; Blessing, 1995)'
_exptl_crystal_colour            'translucent orange'
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.397
_refine_ls_extinction_coef       0.0146(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0742
_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)+(0.0891P)²+1.9474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.2072
_reflns_number_gt                2208
_reflns_number_total             3446
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2400.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        3618.4(9)
_cod_database_code               2213793
_cod_database_fobs_code          2213793
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.93705(17) 0.70977(7) 0.3527(4) 0.0340(6) Uani d . 1
C C2 0.89917(17) 0.72967(7) 0.2033(3) 0.0350(6) Uani d . 1
C C3 0.85410(19) 0.71093(9) 0.0504(4) 0.0424(7) Uani d . 1
C C5 0.98466(18) 0.72940(7) 0.4982(3) 0.0317(6) Uani d . 1
C C6 1.03201(17) 0.70973(7) 0.6438(4) 0.0326(6) Uani d . 1
C C8 1.11360(19) 0.71085(9) 0.9468(4) 0.0396(7) Uani d . 1
C C7 1.06983(17) 0.72991(7) 0.7940(3) 0.0320(6) Uani d . 1
C C4 0.8150(2) 0.73005(9) -0.0912(4) 0.0479(8) Uani d . 1
C C9 1.1524(2) 0.73011(8) 1.0896(4) 0.0440(7) Uani d . 1
H H8 1.1141(19) 0.6838(8) 0.942(4) 0.043(8) Uiso d . 1
H H3 0.8547(19) 0.6831(8) 0.045(4) 0.045(8) Uiso d . 1
H H31 0.948(2) 0.6491(8) 0.807(4) 0.051(8) Uiso d . 1
H H34 1.219(3) 0.6126(10) 0.480(5) 0.074(11) Uiso d . 1
H H25 0.798(2) 0.6770(9) 0.527(5) 0.068(10) Uiso d . 1
H H32 1.000(2) 0.5855(9) 0.807(5) 0.067(10) Uiso d . 1
H H24 0.745(3) 0.6144(11) 0.534(6) 0.092(13) Uiso d . 1
H H35 1.171(2) 0.6769(8) 0.470(4) 0.055(9) Uiso d . 1
H H21 1.019(3) 0.6479(9) 0.194(5) 0.070(10) Uiso d . 1
H H23 0.828(3) 0.5687(11) 0.359(5) 0.081(11) Uiso d . 1
H H4 0.787(2) 0.7156(8) -0.197(4) 0.047(8) Uiso d . 1
H H22 0.964(3) 0.5854(10) 0.196(5) 0.082(12) Uiso d . 1
H H9 1.179(2) 0.7171(8) 1.191(4) 0.057(9) Uiso d . 1
C C20 0.91358(19) 0.66864(7) 0.3598(4) 0.0387(7) Uani d . 1
C C30 1.05447(18) 0.66849(7) 0.6373(4) 0.0361(6) Uani d . 1
C C31 1.0058(2) 0.64137(8) 0.7376(4) 0.0446(7) Uani d . 1
C C21 0.9614(2) 0.64110(8) 0.2608(4) 0.0503(8) Uani d . 1
C C35 1.1346(2) 0.65679(8) 0.5419(4) 0.0455(7) Uani d . 1
C C25 0.8324(2) 0.65765(9) 0.4549(5) 0.0508(8) Uani d . 1
C C24 0.8020(3) 0.62075(10) 0.4534(6) 0.0681(10) Uani d . 1
C C34 1.1634(2) 0.61949(9) 0.5450(5) 0.0569(9) Uani d . 1
C C32 1.0352(3) 0.60433(9) 0.7392(5) 0.0539(8) Uani d . 1
C C33 1.1156(2) 0.59238(8) 0.6449(5) 0.0553(9) Uani d . 1
C C22 0.9308(3) 0.60409(10) 0.2607(6) 0.0661(10) Uani d . 1
C C23 0.8510(3) 0.59405(11) 0.3566(6) 0.0745(11) Uani d . 1
C C40 1.1464(3) 0.55077(10) 0.6420(6) 0.0786(12) Uani d . 1
C C42 1.1059(6) 0.52857(12) 0.8005(9) 0.167(3) Uani d . 1
H H42A 1.0383 0.5278 0.7896 0.200 Uiso calc R 1
H H42B 1.1229 0.5404 0.9153 0.200 Uiso calc R 1
H H42C 1.1305 0.5033 0.7979 0.200 Uiso calc R 1
C C41 1.2544(4) 0.54734(13) 0.6482(8) 0.121(2) Uani d . 1
H H41A 1.2777 0.5588 0.7596 0.146 Uiso calc R 1
H H41B 1.2811 0.5599 0.5427 0.146 Uiso calc R 1
H H41C 1.2719 0.5211 0.6463 0.146 Uiso calc R 1
C C43 1.1162(4) 0.53380(12) 0.4580(8) 0.129(2) Uani d . 1
H H43A 1.1357 0.5078 0.4524 0.155 Uiso calc R 1
H H43B 1.1450 0.5476 0.3585 0.155 Uiso calc R 1
H H43C 1.0487 0.5352 0.4467 0.155 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C5 . . 120.3(2) no
C2 C1 C20 . . 115.6(2) no
C5 C1 C20 . . 123.6(2) no
C1 C2 C3 . . 122.1(2) no
C1 C2 C2 . 8_575 120.30(15) no
C3 C2 C2 . 8_575 117.48(16) no
C4 C3 C2 . . 122.3(3) no
C4 C3 H3 . . 118.4(17) no
C2 C3 H3 . . 119.3(17) no
C6 C5 C1 . . 121.7(2) no
C6 C5 C5 . 8_575 119.17(14) no
C1 C5 C5 . 8_575 119.09(14) no
C7 C6 C5 . . 120.0(2) no
C7 C6 C30 . . 116.1(2) no
C5 C6 C30 . . 123.6(2) no
C9 C8 C7 . . 121.7(3) no
C9 C8 H8 . . 121.8(17) no
C7 C8 H8 . . 116.6(17) no
C6 C7 C7 . 8_575 120.55(14) no
C6 C7 C8 . . 121.3(2) no
C7 C7 C8 8_575 . 118.05(16) no
C3 C4 C4 . 8_575 120.20(18) no
C3 C4 H4 . . 119.0(16) no
C4 C4 H4 8_575 . 120.8(16) no
C8 C9 C9 . 8_575 120.26(18) no
C8 C9 H9 . . 120.8(19) no
C9 C9 H9 8_575 . 119.0(18) no
C21 C20 C25 . . 117.4(3) no
C21 C20 C1 . . 124.0(3) no
C25 C20 C1 . . 118.2(2) no
C31 C30 C35 . . 117.3(3) no
C31 C30 C6 . . 123.7(2) no
C35 C30 C6 . . 118.7(2) no
C32 C31 C30 . . 120.9(3) no
C32 C31 H31 . . 120.2(16) no
C30 C31 H31 . . 118.9(16) no
C22 C21 C20 . . 121.0(3) no
C22 C21 H21 . . 120(2) no
C20 C21 H21 . . 119(2) no
C34 C35 C30 . . 121.2(3) no
C34 C35 H35 . . 121.8(17) no
C30 C35 H35 . . 117.1(16) no
C24 C25 C20 . . 121.2(3) no
C24 C25 H25 . . 121(2) no
C20 C25 H25 . . 117.9(19) no
C23 C24 C25 . . 120.2(4) no
C23 C24 H24 . . 123(2) no
C25 C24 H24 . . 117(2) no
C33 C34 C35 . . 121.9(3) no
C33 C34 H34 . . 119(2) no
C35 C34 H34 . . 119(2) no
C31 C32 C33 . . 122.2(3) no
C31 C32 H32 . . 120(2) no
C33 C32 H32 . . 117.5(19) no
C34 C33 C32 . . 116.5(3) no
C34 C33 C40 . . 121.4(3) no
C32 C33 C40 . . 122.0(3) no
C23 C22 C21 . . 120.3(4) no
C23 C22 H22 . . 119(2) no
C21 C22 H22 . . 121(2) no
C24 C23 C22 . . 119.9(3) no
C24 C23 H23 . . 118(2) no
C22 C23 H23 . . 122(2) no
C42 C40 C43 . . 110.6(4) no
C42 C40 C41 . . 108.5(5) no
C43 C40 C41 . . 106.0(4) no
C42 C40 C33 . . 112.5(4) no
C43 C40 C33 . . 108.1(3) no
C41 C40 C33 . . 111.0(4) no
C40 C42 H42A . . 109.5 no
C40 C42 H42B . . 109.5 no
H42A C42 H42B . . 109.5 no
C40 C42 H42C . . 109.5 no
H42A C42 H42C . . 109.5 no
H42B C42 H42C . . 109.5 no
C40 C41 H41A . . 109.5 no
C40 C41 H41B . . 109.5 no
H41A C41 H41B . . 109.5 no
C40 C41 H41C . . 109.5 no
H41A C41 H41C . . 109.5 no
H41B C41 H41C . . 109.5 no
C40 C43 H43A . . 109.5 no
C40 C43 H43B . . 109.5 no
H43A C43 H43B . . 109.5 no
C40 C43 H43C . . 109.5 no
H43A C43 H43C . . 109.5 no
H43B C43 H43C . . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.396(4) no
C1 C5 . 1.429(4) no
C1 C20 . 1.494(4) no
C2 C3 . 1.437(4) no
C2 C2 8_575 1.439(5) no
C3 C4 . 1.345(4) no
C3 H3 . 0.99(3) no
C5 C6 . 1.428(4) no
C5 C5 8_575 1.458(5) no
C6 C7 . 1.405(4) no
C6 C30 . 1.495(3) no
C8 C9 . 1.353(4) no
C8 C7 . 1.434(4) no
C8 H8 . 0.96(3) no
C7 C7 8_575 1.422(5) no
C4 C4 8_575 1.412(6) no
C4 H4 . 1.00(3) no
C9 C9 8_575 1.408(6) no
C9 H9 . 0.95(3) no
C20 C21 . 1.385(4) no
C20 C25 . 1.395(4) no
C30 C31 . 1.386(4) no
C30 C35 . 1.390(4) no
C31 C32 . 1.376(4) no
C31 H31 . 1.00(3) no
C21 C22 . 1.380(5) no
C21 H21 . 0.98(4) no
C35 C34 . 1.382(4) no
C35 H35 . 1.02(3) no
C25 C24 . 1.375(4) no
C25 H25 . 0.99(3) no
C24 C23 . 1.365(6) no
C24 H24 . 1.02(4) no
C34 C33 . 1.378(5) no
C34 H34 . 0.95(4) no
C32 C33 . 1.392(5) no
C32 H32 . 0.97(3) no
C33 C40 . 1.536(4) no
C22 C23 . 1.371(6) no
C22 H22 . 0.94(4) no
C23 H23 . 0.96(4) no
C40 C42 . 1.502(6) no
C40 C43 . 1.520(6) no
C40 C41 . 1.534(6) no
C42 H42A . 0.9600 no
C42 H42B . 0.9600 no
C42 H42C . 0.9600 no
C41 H41A . 0.9600 no
C41 H41B . 0.9600 no
C41 H41C . 0.9600 no
C43 H43A . 0.9600 no
C43 H43B . 0.9600 no
C43 H43C . 0.9600 no
