#------------------------------------------------------------------------------
#$Date: 2019-09-30 12:15:08 +0300 (Mon, 30 Sep 2019) $
#$Revision: 218931 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/42/7234245.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_7234245
loop_
_publ_author_name
'Madayanad Suresh Subeesh'
'Kanagaraj Shanmugasundaram'
'Chozhidakath Damodharan Sunesh'
'Yong Sun Won'
'Youngson Choe'
_publ_section_title
;
 Utilization of a phenanthroimidazole based fluorophore in light-emitting
 electrochemical cells
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4683
_journal_page_last               4687
_journal_paper_doi               10.1039/C5TC00151J
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C31 H18 N2'
_chemical_formula_weight         418.47
_chemical_name_common            PYPN
_chemical_name_systematic        2-(pyren-1-yl)-1H-phenanthro[9,10-d]imidazole
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   24.4661(10)
_cell_length_b                   24.4661(10)
_cell_length_c                   20.545(2)
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.73
_cell_volume                     10650.4(12)
_computing_cell_refinement       'Bruker AEPX2'
_computing_data_collection       'Bruker AEPX2'
_computing_data_reduction        'Bruker AEPX2'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Breeze 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  0.0684
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17254
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3924
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ether/THF'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0735
_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)+(0.0915P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2145
_reflns_number_gt                2130
_reflns_number_total             4637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-4683.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Rhombohedral' was changed
to 'rhombohedral' in accordance with the built-in table derived from
the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        10650.6(14)
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7234245
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.15977(12) 0.19725(11) -0.03824(11) 0.0548(7) Uani 1 1 d . . .
H1A H 0.1307 0.2083 -0.0358 0.066 Uiso 1 1 calc R . .
N2 N 0.22469(12) 0.16228(12) -0.00865(12) 0.0543(7) Uani 1 1 d . . .
C1 C 0.15100(15) 0.16153(15) 0.07620(15) 0.0504(8) Uani 1 1 d . . .
C2 C 0.18843(15) 0.19275(15) 0.13083(15) 0.0518(8) Uani 1 1 d . . .
C3 C 0.16009(15) 0.17965(15) 0.19292(15) 0.0514(8) Uani 1 1 d . . .
C4 C 0.09465(16) 0.13537(16) 0.20026(16) 0.0585(9) Uani 1 1 d . . .
C5 C 0.05925(16) 0.10600(15) 0.14480(17) 0.0614(9) Uani 1 1 d . . .
H5A H 0.0155 0.0765 0.1488 0.074 Uiso 1 1 calc R . .
C6 C 0.08691(17) 0.11923(15) 0.08443(16) 0.0585(9) Uani 1 1 d . . .
H6A H 0.0617 0.0990 0.0473 0.070 Uiso 1 1 calc R . .
C7 C 0.25466(15) 0.23931(15) 0.12555(16) 0.0552(9) Uani 1 1 d . . .
H7A H 0.2747 0.2492 0.0842 0.066 Uiso 1 1 calc R . .
C8 C 0.28791(16) 0.26853(16) 0.17907(16) 0.0615(9) Uani 1 1 d . . .
H8A H 0.3312 0.2993 0.1741 0.074 Uiso 1 1 calc R . .
C9 C 0.26199(16) 0.25608(16) 0.24242(16) 0.0571(9) Uani 1 1 d . . .
C10 C 0.19708(16) 0.21059(15) 0.24942(15) 0.0555(9) Uani 1 1 d . . .
C11 C 0.16864(19) 0.19643(17) 0.31194(16) 0.0651(10) Uani 1 1 d . . .
C12 C 0.1033(2) 0.15237(19) 0.31738(18) 0.0768(11) Uani 1 1 d . . .
H12A H 0.0840 0.1434 0.3591 0.092 Uiso 1 1 calc R . .
C13 C 0.06763(18) 0.12283(17) 0.26450(19) 0.0747(11) Uani 1 1 d . . .
H13A H 0.0240 0.0933 0.2699 0.090 Uiso 1 1 calc R . .
C14 C 0.29655(18) 0.28595(17) 0.29807(18) 0.0705(10) Uani 1 1 d . . .
H14A H 0.3401 0.3164 0.2940 0.085 Uiso 1 1 calc R . .
C15 C 0.2693(2) 0.2725(2) 0.35881(19) 0.0811(12) Uani 1 1 d . . .
H15A H 0.2940 0.2935 0.3960 0.097 Uiso 1 1 calc R . .
C16 C 0.2059(2) 0.2286(2) 0.36585(18) 0.0775(11) Uani 1 1 d . . .
H16A H 0.1874 0.2200 0.4080 0.093 Uiso 1 1 calc R . .
C17 C 0.17921(15) 0.17358(15) 0.01125(15) 0.0530(8) Uani 1 1 d . . .
C18 C 0.19432(14) 0.20059(13) -0.09288(14) 0.0482(8) Uani 1 1 d . . .
C19 C 0.19108(14) 0.22002(14) -0.15773(14) 0.0508(8) Uani 1 1 d . . .
C20 C 0.23054(14) 0.21338(14) -0.20373(15) 0.0507(8) Uani 1 1 d . . .
C21 C 0.27266(14) 0.18979(14) -0.18447(15) 0.0517(8) Uani 1 1 d . . .
C22 C 0.27552(14) 0.17381(13) -0.11890(15) 0.0495(8) Uani 1 1 d . . .
C23 C 0.23408(14) 0.17988(14) -0.07351(14) 0.0492(8) Uani 1 1 d . . .
C24 C 0.15399(15) 0.24626(15) -0.17574(16) 0.0596(9) Uani 1 1 d . . .
H24A H 0.1278 0.2505 -0.1445 0.072 Uiso 1 1 calc R . .
C25 C 0.15551(17) 0.26587(17) -0.23868(18) 0.0730(11) Uani 1 1 d . . .
H25A H 0.1312 0.2848 -0.2505 0.088 Uiso 1 1 calc R . .
C26 C 0.19199(17) 0.25819(17) -0.28465(17) 0.0687(10) Uani 1 1 d . . .
H26A H 0.1915 0.2706 -0.3284 0.082 Uiso 1 1 calc R . .
C27 C 0.22872(16) 0.23308(15) -0.26828(15) 0.0623(9) Uani 1 1 d . . .
H27A H 0.2538 0.2286 -0.3009 0.075 Uiso 1 1 calc R . .
C28 C 0.31076(16) 0.18092(15) -0.22993(16) 0.0600(9) Uani 1 1 d . . .
H28A H 0.3087 0.1896 -0.2747 0.072 Uiso 1 1 calc R . .
C29 C 0.35064(17) 0.16005(16) -0.21052(18) 0.0697(10) Uani 1 1 d . . .
H29A H 0.3761 0.1549 -0.2420 0.084 Uiso 1 1 calc R . .
C30 C 0.35477(17) 0.14615(15) -0.14531(17) 0.0666(10) Uani 1 1 d . . .
H30A H 0.3834 0.1326 -0.1324 0.080 Uiso 1 1 calc R . .
C31 C 0.31672(15) 0.15240(15) -0.10005(16) 0.0568(9) Uani 1 1 d . . .
H31A H 0.3184 0.1421 -0.0558 0.068 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C17 N1 C18 107.3(3) . .
C17 N1 H1A 126.4 . .
C18 N1 H1A 126.4 . .
C17 N2 C23 104.8(2) . .
C6 C1 C2 119.5(3) . .
C6 C1 C17 120.2(3) . .
C2 C1 C17 120.3(3) . .
C1 C2 C3 119.0(3) . .
C1 C2 C7 122.4(3) . .
C3 C2 C7 118.5(3) . .
C2 C3 C4 120.5(3) . .
C2 C3 C10 120.3(3) . .
C4 C3 C10 119.3(3) . .
C5 C4 C3 118.6(3) . .
C5 C4 C13 122.6(3) . .
C3 C4 C13 118.8(3) . .
C6 C5 C4 120.8(3) . .
C6 C5 H5A 119.6 . .
C4 C5 H5A 119.6 . .
C5 C6 C1 121.7(3) . .
C5 C6 H6A 119.2 . .
C1 C6 H6A 119.2 . .
C8 C7 C2 120.0(3) . .
C8 C7 H7A 120.0 . .
C2 C7 H7A 120.0 . .
C7 C8 C9 123.6(3) . .
C7 C8 H8A 118.2 . .
C9 C8 H8A 118.2 . .
C14 C9 C8 123.6(4) . .
C14 C9 C10 118.4(3) . .
C8 C9 C10 117.9(3) . .
C11 C10 C9 120.2(3) . .
C11 C10 C3 120.1(3) . .
C9 C10 C3 119.7(3) . .
C16 C11 C12 122.4(4) . .
C16 C11 C10 118.5(4) . .
C12 C11 C10 119.1(3) . .
C13 C12 C11 121.6(4) . .
C13 C12 H12A 119.2 . .
C11 C12 H12A 119.2 . .
C12 C13 C4 121.2(4) . .
C12 C13 H13A 119.4 . .
C4 C13 H13A 119.4 . .
C15 C14 C9 121.7(4) . .
C15 C14 H14A 119.2 . .
C9 C14 H14A 119.2 . .
C14 C15 C16 120.1(4) . .
C14 C15 H15A 119.9 . .
C16 C15 H15A 119.9 . .
C15 C16 C11 121.1(4) . .
C15 C16 H16A 119.5 . .
C11 C16 H16A 119.5 . .
N2 C17 N1 111.2(3) . .
N2 C17 C1 126.5(3) . .
N1 C17 C1 122.3(3) . .
C23 C18 N1 105.7(3) . .
C23 C18 C19 124.4(3) . .
N1 C18 C19 130.0(3) . .
C24 C19 C20 120.8(3) . .
C24 C19 C18 123.7(3) . .
C20 C19 C18 115.4(3) . .
C19 C20 C27 116.5(3) . .
C19 C20 C21 121.2(3) . .
C27 C20 C21 122.3(3) . .
C28 C21 C22 117.4(3) . .
C28 C21 C20 122.1(3) . .
C22 C21 C20 120.5(3) . .
C31 C22 C21 120.7(3) . .
C31 C22 C23 122.3(3) . .
C21 C22 C23 117.0(3) . .
C18 C23 N2 111.0(3) . .
C18 C23 C22 121.3(3) . .
N2 C23 C22 127.4(3) . .
C25 C24 C19 119.9(3) . .
C25 C24 H24A 120.0 . .
C19 C24 H24A 120.0 . .
C24 C25 C26 120.3(3) . .
C24 C25 H25A 119.8 . .
C26 C25 H25A 119.8 . .
C27 C26 C25 120.8(3) . .
C27 C26 H26A 119.6 . .
C25 C26 H26A 119.6 . .
C26 C27 C20 121.6(3) . .
C26 C27 H27A 119.2 . .
C20 C27 H27A 119.2 . .
C29 C28 C21 120.9(3) . .
C29 C28 H28A 119.5 . .
C21 C28 H28A 119.5 . .
C28 C29 C30 121.5(3) . .
C28 C29 H29A 119.3 . .
C30 C29 H29A 119.3 . .
C31 C30 C29 119.0(3) . .
C31 C30 H30A 120.5 . .
C29 C30 H30A 120.5 . .
C30 C31 C22 120.4(3) . .
C30 C31 H31A 119.8 . .
C22 C31 H31A 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C17 1.368(4) .
N1 C18 1.383(3) .
N1 H1A 0.8800 .
N2 C17 1.337(4) .
N2 C23 1.384(4) .
C1 C6 1.391(4) .
C1 C2 1.408(4) .
C1 C17 1.463(4) .
C2 C3 1.410(4) .
C2 C7 1.446(4) .
C3 C4 1.423(4) .
C3 C10 1.433(4) .
C4 C5 1.394(4) .
C4 C13 1.439(4) .
C5 C6 1.372(4) .
C5 H5A 0.9500 .
C6 H6A 0.9500 .
C7 C8 1.342(4) .
C7 H7A 0.9500 .
C8 C9 1.413(4) .
C8 H8A 0.9500 .
C9 C14 1.392(4) .
C9 C10 1.419(4) .
C10 C11 1.419(4) .
C11 C16 1.400(5) .
C11 C12 1.418(5) .
C12 C13 1.354(5) .
C12 H12A 0.9500 .
C13 H13A 0.9500 .
C14 C15 1.375(5) .
C14 H14A 0.9500 .
C15 C16 1.383(5) .
C15 H15A 0.9500 .
C16 H16A 0.9500 .
C18 C23 1.362(4) .
C18 C19 1.430(4) .
C19 C24 1.398(4) .
C19 C20 1.417(4) .
C20 C27 1.419(4) .
C20 C21 1.465(4) .
C21 C28 1.411(4) .
C21 C22 1.414(4) .
C22 C31 1.403(4) .
C22 C23 1.439(4) .
C24 C25 1.373(4) .
C24 H24A 0.9500 .
C25 C26 1.375(5) .
C25 H25A 0.9500 .
C26 C27 1.360(4) .
C26 H26A 0.9500 .
C27 H27A 0.9500 .
C28 C29 1.367(4) .
C28 H28A 0.9500 .
C29 C30 1.398(4) .
C29 H29A 0.9500 .
C30 C31 1.377(4) .
C30 H30A 0.9500 .
C31 H31A 0.9500 .
