#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/59/2005908.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_2005908
loop_
_publ_author_name
'Venkataraman, D.'
'Wang, P.-W.'
'Moore, J. S.'
_publ_contact_author
;
Jeffrey S. Moore
Departments of Chemistry and
Materials Science & Engineering and
The Beckman Institute for Advanced Science and Technology
University of Illinois
600 South Mathews Avenue, Box 55-5
Urbana, Illinois  61801
USA
;
_publ_section_title
;
 9,10-Bis{2-[4-(N,N-diphenylamino)phenyl]ethynyl}anthracene
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              241
_journal_page_last               243
_journal_paper_doi               10.1107/S0108270196012620
_journal_volume                  53
_journal_year                    1997
_chemical_formula_analytical     'C54 H36 N2'
_chemical_formula_moiety         'C54 H36 N2'
_chemical_formula_structural     'C108 H72 N4'
_chemical_formula_sum            'C54 H36 N2'
_chemical_formula_weight         712.85
_chemical_name_common            wwanthra
_chemical_name_systematic
;
9,10-bis[2-ethynyl(4-N,N-diphenylamino)phenyl]anthracene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 108.14(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.582(2)
_cell_length_b                   9.407(2)
_cell_length_c                   18.429(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      9.94
_cell_measurement_theta_min      9.36
_cell_volume                     1908.1(7)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'CAD4 Software and PROFILE (Blessing, Coppens & Becker, 1972)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1971)'
_computing_publication_material  'CIFTAB SHELXL93'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       'ω-θ scan profiles'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2958
_diffrn_reflns_theta_max         23.47
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0.09
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       prism
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.040
_refine_ls_goodness_of_fit_obs   1.071
_refine_ls_hydrogen_treatment
; H-atom coordinates refined, U~eq~(H) constrained to single free variable
and refined
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_restrained_S_obs      1.071
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_obs          0.0438
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.057P)²+0.3764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1228
_refine_ls_wR_factor_obs         0.1057
_reflns_number_observed          2042
_reflns_number_total             2802
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            bk1186.cif
_cod_data_source_block           w45qa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.057P)^2^+0.3764P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.057P)^2^+0.3764P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2005908
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
N1 1 0.8507(2) 0.0919(2) 0.19874(10) 0.0545(5) Uani d N
C1 1 1.1537(2) 0.8794(3) 0.13731(14) 0.0627(7) Uani d C
H1 1 1.1344(21) 0.7788(27) 0.1496(13) 0.075(2) Uiso d H
C2 1 1.2478(2) 0.9553(3) 0.1826(2) 0.0771(8) Uani d C
H2 1 1.2997(22) 0.9108(26) 0.2258(14) 0.075(2) Uiso d H
C3 1 0.7313(2) 0.9047(3) -0.1636(2) 0.0781(8) Uani d C
H3 1 0.6658(23) 0.8501(26) -0.1949(14) 0.075(2) Uiso d H
C4 1 0.8036(2) 0.8447(3) -0.0985(2) 0.0656(7) Uani d C
H4 1 0.7903(22) 0.7503(28) -0.0852(14) 0.075(2) Uiso d H
C9 1 0.9761(2) 0.8607(2) 0.02073(12) 0.0483(5) Uani d C
C11 1 1.0745(2) 0.9384(2) 0.06875(12) 0.0490(5) Uani d C
C12 1 0.9019(2) 0.9209(2) -0.04827(12) 0.0492(5) Uani d C
C13 1 0.9508(2) 0.7211(2) 0.04297(13) 0.0534(6) Uani d C
C14 1 0.9307(2) 0.6073(2) 0.06485(13) 0.0531(6) Uani d C
C15 1 0.9080(2) 0.4754(2) 0.09713(12) 0.0488(5) Uani d C
C16 1 0.8512(2) 0.3608(2) 0.05313(13) 0.0531(6) Uani d C
H16 1 0.8266(21) 0.3665(25) -0.0012(15) 0.075(2) Uiso d H
C17 1 0.8323(2) 0.2359(2) 0.08601(12) 0.0520(6) Uani d C
H17 1 0.7981(22) 0.1599(26) 0.0561(14) 0.075(2) Uiso d H
C18 1 0.8693(2) 0.2199(2) 0.16495(11) 0.0467(5) Uani d C
C19 1 0.9236(2) 0.3352(2) 0.20929(13) 0.0511(6) Uani d C
H19 1 0.9485(22) 0.3297(25) 0.2621(15) 0.075(2) Uiso d H
C20 1 0.9427(2) 0.4604(2) 0.17633(13) 0.0533(6) Uani d C
H20 1 0.9795(21) 0.5427(26) 0.2073(14) 0.075(2) Uiso d H
C21 1 0.9333(2) 0.0438(2) 0.26896(12) 0.0501(5) Uani d C
C22 1 0.8914(2) -0.0263(2) 0.32163(13) 0.0581(6) Uani d C
H22 1 0.8054(23) -0.0411(26) 0.3103(14) 0.075(2) Uiso d H
C23 1 0.9726(3) -0.0704(3) 0.39027(15) 0.0672(7) Uani d C
H23 1 0.9428(22) -0.1178(26) 0.4262(14) 0.075(2) Uiso d H
C24 1 1.0933(3) -0.0461(3) 0.4069(2) 0.0722(7) Uani d C
H24 1 1.1503(22) -0.0758(26) 0.4544(14) 0.075(2) Uiso d H
C25 1 1.1358(3) 0.0207(3) 0.3542(2) 0.0755(8) Uani d C
H25 1 1.2259(23) 0.0359(25) 0.3645(13) 0.075(2) Uiso d H
C26 1 1.0569(2) 0.0660(3) 0.28544(15) 0.0650(7) Uani d C
H26 1 1.0867(21) 0.1095(26) 0.2472(14) 0.075(2) Uiso d H
C27 1 0.7489(2) 0.0051(2) 0.15992(12) 0.0501(5) Uani d C
C28 1 0.6329(2) 0.0592(3) 0.13961(14) 0.0628(7) Uani d C
H28 1 0.6265(22) 0.1543(28) 0.1546(14) 0.075(2) Uiso d H
C29 1 0.5357(3) -0.0255(4) 0.09934(15) 0.0769(8) Uani d C
H29 1 0.4613(23) 0.0137(27) 0.0889(14) 0.075(2) Uiso d H
C30 1 0.5562(4) -0.1632(4) 0.0817(2) 0.0840(10) Uani d C
H30 1 0.4895(23) -0.2199(28) 0.0580(14) 0.075(2) Uiso d H
C31 1 0.6706(4) -0.2156(3) 0.1030(2) 0.0811(9) Uani d C
H31 1 0.6862(21) -0.3126(28) 0.0882(14) 0.075(2) Uiso d H
C32 1 0.7672(3) -0.1334(3) 0.14187(15) 0.0659(7) Uani d C
H32 1 0.8499(23) -0.1728(26) 0.1546(14) 0.075(2) Uiso d H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C18 N1 C21 . 121.6(2) yes
C18 N1 C27 . 119.0(2) yes
C21 N1 C27 . 119.3(2) yes
C2 C1 C11 . 121.1(2) ?
C1 C2 C3 3_775 120.6(3) ?
C4 C3 C2 3_775 120.4(3) ?
C3 C4 C12 . 121.1(2) ?
C11 C9 C12 . 120.3(2) ?
C11 C9 C13 . 119.5(2) ?
C12 C9 C13 . 120.2(2) ?
C9 C11 C1 . 121.8(2) ?
C9 C11 C12 3_775 119.9(2) ?
C1 C11 C12 3_775 118.2(2) ?
C9 C12 C4 . 121.7(2) ?
C9 C12 C11 3_775 119.8(2) ?
C4 C12 C11 3_775 118.5(2) ?
C14 C13 C9 . 176.9(2) ?
C13 C14 C15 . 175.4(2) ?
C16 C15 C20 . 117.6(2) ?
C16 C15 C14 . 123.0(2) ?
C20 C15 C14 . 119.4(2) ?
C17 C16 C15 . 121.4(2) ?
C16 C17 C18 . 121.0(2) ?
C19 C18 C17 . 117.9(2) ?
C19 C18 N1 . 120.9(2) yes
C17 C18 N1 . 121.2(2) yes
C20 C19 C18 . 121.1(2) ?
C19 C20 C15 . 121.0(2) ?
C22 C21 C26 . 118.9(2) ?
C22 C21 N1 . 120.5(2) ?
C26 C21 N1 . 120.6(2) ?
C21 C22 C23 . 119.9(2) ?
C24 C23 C22 . 121.1(3) ?
C23 C24 C25 . 119.3(3) ?
C24 C25 C26 . 120.8(3) ?
C25 C26 C21 . 120.0(2) ?
C28 C27 C32 . 119.7(2) ?
C28 C27 N1 . 120.5(2) ?
C32 C27 N1 . 119.8(2) ?
C27 C28 C29 . 119.5(3) ?
C30 C29 C28 . 119.7(3) ?
C31 C30 C29 . 120.1(3) ?
C30 C31 C32 . 121.0(3) ?
C31 C32 C27 . 120.0(3) ?
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
N1 C18 . 1.403(2) yes
N1 C21 . 1.423(3) yes
N1 C27 . 1.430(3) yes
C1 C2 . 1.352(4) yes
C1 C11 . 1.422(3) yes
C2 C3 3_775 1.404(4) yes
C3 C4 . 1.354(4) yes
C3 C2 3_775 1.404(4) yes
C4 C12 . 1.418(3) yes
C9 C11 . 1.410(3) yes
C9 C12 . 1.413(3) yes
C9 C13 . 1.433(3) yes
C11 C12 3_775 1.426(3) yes
C12 C11 3_775 1.426(3) yes
C13 C14 . 1.192(3) yes
C14 C15 . 1.435(3) yes
C15 C16 . 1.386(3) yes
C15 C20 . 1.395(3) yes
C16 C17 . 1.371(3) yes
C17 C18 . 1.391(3) yes
C18 C19 . 1.385(3) yes
C19 C20 . 1.375(3) yes
C21 C22 . 1.380(3) yes
C21 C26 . 1.383(3) yes
C22 C23 . 1.384(3) yes
C23 C24 . 1.354(4) yes
C24 C25 . 1.370(4) yes
C25 C26 . 1.379(3) yes
C27 C28 . 1.375(3) yes
C27 C32 . 1.377(3) yes
C28 C29 . 1.390(4) yes
C29 C30 . 1.374(4) yes
C30 C31 . 1.352(4) yes
C31 C32 . 1.365(4) yes
