#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/89/1508945.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_1508945
loop_
_publ_author_name
'Zöphel, Lukas'
'Enkelmann, Volker'
'Müllen, Klaus'
_publ_section_title
;
 Tuning the HOMO-LUMO Gap of Pyrene Effectively via Donor-Acceptor
 Substitution: Positions 4,5 Versus 9,10.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              804
_journal_page_last               807
_journal_paper_doi               10.1021/ol303476g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C28 H22 N4'
_chemical_formula_sum            'C28 H22 N4'
_chemical_formula_weight         414.51
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-12-17
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 97.088(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0368(3)
_cell_length_b                   9.2187(5)
_cell_length_c                   13.5180(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1117.55(9)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10908
_diffrn_reflns_theta_full        30.382
_diffrn_reflns_theta_max         31.002
_diffrn_reflns_theta_min         3.169
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       prism
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.66
_refine_diff_density_min         -0.73
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0775
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.000162
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;

 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 

 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 

 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 

 Method = Robust Weighting (Prince, 1982) 

 W = [weight] * [1-(deltaF/6*sigmaF)²]² 

 Ai are: 

 2.91 1.75 2.00 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1221
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.0988
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2034
_reflns_number_total             3549
_reflns_threshold_expression     I>3.0σ(I)
_cod_data_source_file            ol303476g_si_007.cif
_cod_data_source_block           4cn2tbupy
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1117.54(9)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               1508945
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
N15 N 0.8117(3) 0.2608(4) 0.2667(3) 0.0803 1.0000 Uani .
N16 N 1.0022(3) -0.0991(3) 0.38161(17) 0.0458 1.0000 Uani .
C1 C 0.7539(3) 0.1917(3) 0.3212(2) 0.0492 1.0000 Uani .
C2 C 0.6792(2) 0.1057(3) 0.38879(16) 0.0331 1.0000 Uani .
C3 C 0.5379(2) 0.1543(2) 0.41530(15) 0.0303 1.0000 Uani .
C4 C 0.4714(3) 0.2839(3) 0.37914(17) 0.0361 1.0000 Uani .
C5 C 0.3363(3) 0.3315(3) 0.40734(17) 0.0349 1.0000 Uani .
C6 C 0.2649(2) 0.2430(2) 0.46988(16) 0.0330 1.0000 Uani .
C7 C 0.3274(2) 0.1112(2) 0.50707(14) 0.0278 1.0000 Uani .
C8 C 0.4670(2) 0.0659(2) 0.48105(14) 0.0264 1.0000 Uani .
C9 C 0.7447(2) -0.0209(2) 0.42695(15) 0.0301 1.0000 Uani .
C10 C 0.8880(3) -0.0635(3) 0.39984(17) 0.0351 1.0000 Uani .
C11 C 0.2692(3) 0.4777(3) 0.3714(2) 0.0467 1.0000 Uani .
C12 C 0.3912(4) 0.5859(3) 0.3504(3) 0.0663 1.0000 Uani .
C13 C 0.1643(8) 0.4556(5) 0.2790(6) 0.1685 1.0000 Uani .
C14 C 0.1927(6) 0.5477(4) 0.4541(4) 0.0962 1.0000 Uani .
H41 H 0.5207 0.3417 0.3351 0.0449 1.0000 Uiso R
H61 H 0.1713 0.2726 0.4882 0.0408 1.0000 Uiso R
H121 H 0.3466 0.6752 0.3280 0.0821 1.0000 Uiso R
H122 H 0.4568 0.6016 0.4100 0.0821 1.0000 Uiso R
H123 H 0.4457 0.5475 0.3006 0.0821 1.0000 Uiso R
H131 H 0.1227 0.5459 0.2562 0.1327 1.0000 Uiso R
H132 H 0.2251 0.4189 0.2322 0.1327 1.0000 Uiso R
H133 H 0.0864 0.3887 0.2861 0.1327 1.0000 Uiso R
H141 H 0.1509 0.6385 0.4323 0.1044 1.0000 Uiso R
H142 H 0.2652 0.5621 0.5103 0.1044 1.0000 Uiso R
H143 H 0.1162 0.4858 0.4719 0.1044 1.0000 Uiso R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N15 . C1 C2 179.1(3) yes
C1 . C2 C3 119.1(2) yes
C1 . C2 C9 119.4(2) yes
C3 . C2 C9 121.5(2) yes
C2 . C3 C4 122.3(2) yes
C2 . C3 C8 117.41(19) yes
C4 . C3 C8 120.24(19) yes
C3 . C4 C5 121.8(2) yes
C3 . C4 H41 118.9 no
C5 . C4 H41 119.3 no
C4 . C5 C6 118.0(2) yes
C4 . C5 C11 121.0(2) yes
C6 . C5 C11 121.0(2) yes
C5 . C6 C7 121.9(2) yes
C5 . C6 H61 119.0 no
C7 . C6 H61 119.1 no
C9 2_656 C7 C6 122.02(18) yes
C9 2_656 C7 C8 118.11(18) yes
C6 . C7 C8 119.85(19) yes
C8 2_656 C8 C3 121.1(2) yes
C8 2_656 C8 C7 120.7(2) yes
C3 . C8 C7 118.18(18) yes
C7 2_656 C9 C2 121.11(19) yes
C7 2_656 C9 C10 119.40(19) yes
C2 . C9 C10 119.5(2) yes
C9 . C10 N16 177.7(3) yes
C5 . C11 C12 111.4(2) yes
C5 . C11 C13 109.4(3) yes
C12 . C11 C13 109.4(4) yes
C5 . C11 C14 109.7(3) yes
C12 . C11 C14 105.1(3) yes
C13 . C11 C14 111.9(5) yes
C11 . C12 H121 109.6 no
C11 . C12 H122 109.2 no
H121 . C12 H122 109.5 no
C11 . C12 H123 109.6 no
H121 . C12 H123 109.5 no
H122 . C12 H123 109.5 no
C11 . C13 H131 109.8 no
C11 . C13 H132 104.3 no
H131 . C13 H132 109.5 no
C11 . C13 H133 114.1 no
H131 . C13 H133 109.5 no
H132 . C13 H133 109.5 no
C11 . C14 H141 110.1 no
C11 . C14 H142 108.3 no
H141 . C14 H142 109.5 no
C11 . C14 H143 109.9 no
H141 . C14 H143 109.5 no
H142 . C14 H143 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
N15 C1 . 1.147(3) yes
N16 C10 . 1.139(3) yes
C1 C2 . 1.439(3) yes
C2 C3 . 1.440(3) yes
C2 C9 . 1.379(3) yes
C3 C4 . 1.398(3) yes
C3 C8 . 1.416(3) yes
C4 C5 . 1.394(3) yes
C4 H41 . 0.950 no
C5 C6 . 1.390(3) yes
C5 C11 . 1.532(3) yes
C6 C7 . 1.406(3) yes
C6 H61 . 0.950 no
C7 C9 2_656 1.434(3) yes
C7 C8 . 1.414(3) yes
C8 C8 2_656 1.420(4) yes
C9 C10 . 1.443(3) yes
C11 C12 . 1.538(5) yes
C11 C13 . 1.486(5) yes
C11 C14 . 1.528(5) yes
C12 H121 . 0.950 no
C12 H122 . 0.950 no
C12 H123 . 0.950 no
C13 H131 . 0.950 no
C13 H132 . 0.950 no
C13 H133 . 0.950 no
C14 H141 . 0.950 no
C14 H142 . 0.950 no
C14 H143 . 0.950 no
