#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:04:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180371 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/40/7204037.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_7204037
loop_
_publ_author_name
'Saito, Gunzi'
'Hirate, Seiji'
'Nishimura, Kazukuni'
'Yamochi, Hideki'
_publ_section_title
;
 Nature of the strong electron donor
 1,3,6,8-tetrakis(dimethylamino)pyrene and ionicity of its charge
 transfer complexes
;
_journal_issue                   3
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              723
_journal_paper_doi               10.1039/b007319i
_journal_volume                  11
_journal_year                    2001
_chemical_formula_moiety         'C24 H30 N4'
_chemical_formula_sum            'C24 H30 N4'
_chemical_formula_weight         374.52
_chemical_melting_point          479.70(5)
_chemical_name_common            1,3,6,8-tetrakis(dimethylamino)pyrene
_chemical_name_systematic
; 
1,3,6,8-tetrakis(dimethylamino)pyrene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.866(14)
_cell_angle_beta                 98.569(15)
_cell_angle_gamma                107.584(15)
_cell_formula_units_Z            2
_cell_length_a                   9.349(2)
_cell_length_b                   12.953(2)
_cell_length_c                   9.294(2)
_cell_measurement_reflns_used    3786
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55
_cell_measurement_theta_min      4
_cell_volume                     998.6(4)
_computing_cell_refinement       'MXC(MAC Science)'
_computing_data_collection       'MXC(MAC Science)'
_computing_data_reduction        Crystan
_computing_molecular_graphics    'ORTEP III'
_computing_publication_material
;
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 12.5
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Mac ScienceMXC-DIP2020K'
_diffrn_measurement_method       'Imageing plate (omega-scan)'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3786
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.35
_diffrn_standards_interval_time  1080
_diffrn_standards_number         46
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  none
_exptl_absorpt_correction_T_min  none
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.935
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1112
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2986
_refine_ls_wR_factor_ref         0.3143
_reflns_number_gt                2519
_reflns_number_total             3786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b007319i.txt
_cod_data_source_block           TDAP
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '206.5-206.6 C' was changed to
'479.70(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_database_code               7204037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.6263(4) -0.0392(3) 0.7307(4) 0.0452(8) Uani 1 1 d . . .
H1 H 0.6547 -0.0722 0.8062 0.050 Uiso 1 1 calc R . .
C2 C 0.7269(4) 0.0630(3) 0.7322(4) 0.0459(9) Uani 1 1 d . . .
H2 H 0.8237 0.1006 0.8095 0.050 Uiso 1 1 calc R . .
C3 C 0.6915(4) 0.1145(3) 0.6227(4) 0.0388(8) Uani 1 1 d . . .
C4 C 0.7908(4) 0.2229(3) 0.6252(4) 0.0413(8) Uani 1 1 d . . .
C5 C 0.7604(4) 0.2606(3) 0.5026(4) 0.0439(8) Uani 1 1 d . . .
H5 H 0.8327 0.3313 0.5025 0.050 Uiso 1 1 calc R . .
C6 C 0.6305(4) 0.2008(3) 0.3799(4) 0.0420(8) Uani 1 1 d . . .
C7 C 0.5198(4) 0.0979(3) 0.3805(4) 0.0383(8) Uani 1 1 d . . .
C8 C 0.5539(3) 0.0546(2) 0.5009(3) 0.0364(8) Uani 1 1 d . . .
C9 C 0.8879(6) 0.3314(4) 0.9007(5) 0.0737(13) Uani 1 1 d . . .
H9A H 0.8688 0.4011 0.9070 0.050 Uiso 1 1 calc R . .
H9B H 0.9747 0.3470 0.9836 0.050 Uiso 1 1 calc R . .
H9C H 0.7978 0.2753 0.9087 0.050 Uiso 1 1 calc R . .
C10 C 1.0422(5) 0.3825(4) 0.7372(6) 0.0774(14) Uani 1 1 d . . .
H10A H 1.0777 0.3553 0.6475 0.050 Uiso 1 1 calc R . .
H10B H 1.1275 0.4153 0.8275 0.050 Uiso 1 1 calc R . .
H10C H 1.0006 0.4400 0.7263 0.050 Uiso 1 1 calc R . .
C11 C 0.6921(6) 0.3572(4) 0.2739(6) 0.0720(13) Uani 1 1 d . . .
H11A H 0.6837 0.4079 0.3665 0.050 Uiso 1 1 calc R . .
H11B H 0.6540 0.3762 0.1866 0.050 Uiso 1 1 calc R . .
H11C H 0.7988 0.3654 0.2815 0.050 Uiso 1 1 calc R . .
C12 C 0.6023(6) 0.1659(5) 0.1067(5) 0.0789(14) Uani 1 1 d . . .
H12A H 0.7073 0.1820 0.0983 0.050 Uiso 1 1 calc R . .
H12B H 0.5440 0.1804 0.0252 0.050 Uiso 1 1 calc R . .
H12C H 0.5566 0.0868 0.0983 0.050 Uiso 1 1 calc R . .
N13 N 0.9222(3) 0.2869(3) 0.7527(4) 0.0540(9) Uani 1 1 d . . .
N14 N 0.6010(4) 0.2389(3) 0.2540(3) 0.0506(8) Uani 1 1 d . . .
C21 C 0.3917(5) 0.5500(3) 0.2335(4) 0.0497(9) Uani 1 1 d . . .
H21 H 0.3341 0.5496 0.3107 0.050 Uiso 1 1 calc R . .
C22 C 0.4923(4) 0.6524(3) 0.2358(4) 0.0494(9) Uani 1 1 d . . .
H22 H 0.5036 0.7224 0.3142 0.050 Uiso 1 1 calc R . .
C23 C 0.5794(4) 0.6569(3) 0.1252(4) 0.0416(8) Uani 1 1 d . . .
C24 C 0.6900(4) 0.7623(3) 0.1284(4) 0.0462(9) Uani 1 1 d . . .
C25 C 0.7580(4) 0.7628(3) 0.0060(4) 0.0510(9) Uani 1 1 d . . .
H25 H 0.8286 0.8346 0.0072 0.050 Uiso 1 1 calc R . .
C26 C 0.7289(4) 0.6642(3) -0.1188(4) 0.0452(9) Uani 1 1 d . . .
C27 C 0.6298(4) 0.5567(3) -0.1190(4) 0.0407(8) Uani 1 1 d . . .
C28 C 0.5530(4) 0.5537(3) 0.0011(3) 0.0387(8) Uani 1 1 d . . .
C29 C 0.8100(8) 0.8617(5) 0.3968(6) 0.111(2) Uani 1 1 d . . .
H29A H 0.7773 0.7851 0.4010 0.050 Uiso 1 1 calc R . .
H29B H 0.7916 0.9121 0.4831 0.050 Uiso 1 1 calc R . .
H29C H 0.9186 0.8879 0.4009 0.050 Uiso 1 1 calc R . .
C30 C 0.8086(6) 0.9720(4) 0.2439(7) 0.0807(15) Uani 1 1 d . . .
H30A H 0.9126 0.9768 0.2413 0.050 Uiso 1 1 calc R . .
H30B H 0.8111 1.0325 0.3325 0.050 Uiso 1 1 calc R . .
H30C H 0.7591 0.9800 0.1516 0.050 Uiso 1 1 calc R . .
C31 C 0.9285(6) 0.7714(4) -0.2196(6) 0.0750(13) Uani 1 1 d . . .
H31A H 0.8930 0.8341 -0.2159 0.050 Uiso 1 1 calc R . .
H31B H 0.9778 0.7590 -0.3029 0.050 Uiso 1 1 calc R . .
H31C H 1.0013 0.7896 -0.1237 0.050 Uiso 1 1 calc R . .
C32 C 0.6853(6) 0.6437(4) -0.3890(5) 0.0716(13) Uani 1 1 d . . .
H32A H 0.5910 0.5829 -0.3992 0.050 Uiso 1 1 calc R . .
H32B H 0.7282 0.6209 -0.4747 0.050 Uiso 1 1 calc R . .
H32C H 0.6637 0.7118 -0.3878 0.050 Uiso 1 1 calc R . .
N33 N 0.7228(4) 0.8618(3) 0.2536(4) 0.0601(9) Uani 1 1 d . . .
N34 N 0.7967(4) 0.6674(3) -0.2444(4) 0.0574(9) 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'
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
_geom_angle_publ_flag
C2 C1 C7 121.4(3) . 2_656 ?
C1 C2 C3 121.6(3) . . ?
C2 C3 C4 122.8(3) . . ?
C2 C3 C8 119.2(3) . . ?
C4 C3 C8 117.9(3) . . ?
C5 C4 N13 122.2(3) . . ?
C5 C4 C3 119.6(3) . . ?
N13 C4 C3 118.1(3) . . ?
C4 C5 C6 122.8(3) . . ?
C5 C6 N14 122.6(3) . . ?
C5 C6 C7 119.3(3) . . ?
N14 C6 C7 118.1(3) . . ?
C8 C7 C6 118.4(3) . . ?
C8 C7 C1 118.7(3) . 2_656 ?
C6 C7 C1 122.8(3) . 2_656 ?
C7 C8 C3 121.4(3) . . ?
C7 C8 C8 119.4(3) . 2_656 ?
C3 C8 C8 119.2(4) . 2_656 ?
C4 N13 C10 117.5(3) . . ?
C4 N13 C9 115.3(3) . . ?
C10 N13 C9 106.4(3) . . ?
C6 N14 C12 115.7(3) . . ?
C6 N14 C11 116.8(3) . . ?
C12 N14 C11 108.3(4) . . ?
C22 C21 C27 121.8(3) . 2_665 ?
C21 C22 C23 121.0(3) . . ?
C22 C23 C24 122.3(3) . . ?
C22 C23 C28 119.3(3) . . ?
C24 C23 C28 118.4(3) . . ?
C25 C24 N33 122.2(3) . . ?
C25 C24 C23 119.2(3) . . ?
N33 C24 C23 118.6(3) . . ?
C24 C25 C26 123.1(3) . . ?
C25 C26 N34 122.0(3) . . ?
C25 C26 C27 119.0(3) . . ?
N34 C26 C27 118.9(3) . . ?
C28 C27 C26 119.2(3) . . ?
C28 C27 C21 118.3(3) . 2_665 ?
C26 C27 C21 122.4(3) . 2_665 ?
C27 C28 C23 120.7(3) . . ?
C27 C28 C28 120.0(4) . 2_665 ?
C23 C28 C28 119.3(4) . 2_665 ?
C24 N33 C30 119.1(4) . . ?
C24 N33 C29 113.5(4) . . ?
C30 N33 C29 103.4(4) . . ?
C26 N34 C31 116.3(3) . . ?
C26 N34 C32 113.6(3) . . ?
C31 N34 C32 108.3(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.368(5) . ?
C1 C7 1.427(5) 2_656 ?
C2 C3 1.412(5) . ?
C3 C4 1.422(4) . ?
C3 C8 1.422(4) . ?
C4 C5 1.382(5) . ?
C4 N13 1.420(4) . ?
C5 C6 1.383(5) . ?
C6 N14 1.411(4) . ?
C6 C7 1.421(4) . ?
C7 C8 1.419(4) . ?
C7 C1 1.427(5) 2_656 ?
C8 C8 1.461(6) 2_656 ?
C9 N13 1.461(5) . ?
C10 N13 1.456(5) . ?
C11 N14 1.455(5) . ?
C12 N14 1.440(5) . ?
C21 C22 1.368(5) . ?
C21 C27 1.430(5) 2_665 ?
C22 C23 1.406(5) . ?
C23 C24 1.431(5) . ?
C23 C28 1.433(5) . ?
C24 C25 1.384(5) . ?
C24 N33 1.395(5) . ?
C25 C26 1.392(5) . ?
C26 N34 1.414(5) . ?
C26 C27 1.419(4) . ?
C27 C28 1.417(5) . ?
C27 C21 1.430(5) 2_665 ?
C28 C28 1.436(6) 2_665 ?
C29 N33 1.454(7) . ?
C30 N33 1.446(5) . ?
C31 N34 1.459(5) . ?
C32 N34 1.466(5) . ?
