#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/50/2205008.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_2205008
loop_
_publ_author_name
'Mizuguchi, Jin'
'Hino, Kazuyuki'
'Sato, Kazuyuki'
'Takahashi, Hiroo'
'Suzuki, Shigeru'
_publ_section_title
;
 N,N'-Di-3-pyridylperylene-3,4:9,10-bis(dicarboximide)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o434
_journal_page_last               o436
_journal_paper_doi               10.1107/S1600536805001996
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C34 H16 N4 O4'
_chemical_formula_moiety         'C34 H16 N4 O4'
_chemical_formula_sum            'C34 H16 N4 O4'
_chemical_formula_weight         544.51
_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'
_cell_angle_alpha                90
_cell_angle_beta                 103.290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.422(2)
_cell_length_b                   3.8275(6)
_cell_length_c                   19.282(3)
_cell_measurement_reflns_used    6312
_cell_measurement_temperature    93.2
_cell_measurement_theta_max      65.5
_cell_measurement_theta_min      3.2
_cell_volume                     1107.7(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation, 2001)
;
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9435
_diffrn_measured_fraction_theta_max 0.9435
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID Imaging Plate'
_diffrn_measurement_method       '48 frames, δ ω = 15°'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10013
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             560.0
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1922
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + {0.025[Max(Fo²,0) + 2Fc²]/3}²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                1009
_reflns_number_total             1922
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            bt6588.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2205008
_cod_database_fobs_code          2205008
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
loop_
_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_occupancy
_atom_site_type_symbol
O1 0.83060(10) -0.1188(5) 0.19907(9) 0.0227(6) Uani d 1.00 O
O2 0.89850(10) 0.4268(5) 0.00748(8) 0.0207(6) Uani d 1.00 O
N1 0.86660(10) 0.1795(6) 0.10660(10) 0.0162(6) Uani d 1.00 N
N2 1.07170(10) 0.2756(6) 0.24800(10) 0.0231(7) Uani d 1.00 N
C1 0.8051(2) 0.0532(8) 0.14480(10) 0.0184(8) Uani d 1.00 C
C2 0.7105(2) 0.1410(8) 0.11620(10) 0.0160(8) Uani d 1.00 C
C3 0.6489(2) 0.0433(8) 0.15440(10) 0.0181(8) Uani d 1.00 C
C4 0.5593(2) 0.1306(7) 0.12930(10) 0.0178(8) Uani d 1.00 C
C5 0.5292(2) 0.3160(7) 0.06690(10) 0.0160(7) Uani d 1.00 C
C6 0.5920(2) 0.4077(8) 0.02560(10) 0.0155(7) Uani d 1.00 C
C7 0.5650(2) 0.5867(7) -0.04110(10) 0.0142(8) Uani d 1.00 C
C8 0.6289(2) 0.6650(8) -0.07940(10) 0.0176(7) Uani d 1.00 C
C9 0.7182(2) 0.5800(7) -0.05300(10) 0.0175(8) Uani d 1.00 C
C10 0.7463(2) 0.4150(7) 0.01180(10) 0.0153(8) Uani d 1.00 C
C11 0.8422(2) 0.3444(8) 0.03950(10) 0.0170(8) Uani d 1.00 C
C12 0.6832(2) 0.3230(8) 0.05150(10) 0.0146(8) Uani d 1.00 C
C13 1.1304(2) 0.1119(7) 0.21730(10) 0.0227(8) Uani d 1.00 C
C14 1.1093(2) -0.0284(8) 0.14940(10) 0.0199(8) Uani d 1.00 C
C15 1.0214(2) -0.0139(8) 0.11020(10) 0.0194(8) Uani d 1.00 C
C16 0.9602(2) 0.1500(8) 0.14120(10) 0.0174(8) Uani d 1.00 C
C17 0.9882(2) 0.2935(8) 0.20900(10) 0.0198(8) Uani d 1.00 C
H1 0.6675 -0.0830 0.1977 0.0217 Uiso calc 1.00 H
H2 0.5176 0.0603 0.1560 0.0214 Uiso calc 1.00 H
H3 0.6113 0.7783 -0.1243 0.0211 Uiso calc 1.00 H
H4 0.7605 0.6366 -0.0802 0.0210 Uiso calc 1.00 H
H5 1.1902 0.0915 0.2439 0.0272 Uiso calc 1.00 H
H6 1.1542 -0.1332 0.1298 0.0239 Uiso calc 1.00 H
H7 1.0043 -0.1131 0.0639 0.0233 Uiso calc 1.00 H
H8 0.9453 0.4115 0.2287 0.0237 Uiso calc 1.00 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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
C1 N1 C11 . . 124.1(2) yes
C1 N1 C16 . . 116.8(2) no
C11 N1 C16 . . 119.0(2) no
C13 N2 C17 . . 115.8(2) no
O1 C1 N1 . . 120.5(2) yes
O1 C1 C2 . . 122.6(2) yes
N1 C1 C2 . . 116.9(2) yes
C1 C2 C3 . . 118.7(2) yes
C1 C2 C12 . . 120.9(2) yes
C3 C2 C12 . . 120.4(2) yes
C2 C3 C4 . . 119.9(2) yes
C2 C3 H1 . . 120.0 no
C4 C3 H1 . . 120.1 no
C3 C4 C5 . . 122.2(2) yes
C3 C4 H2 . . 119.2 no
C5 C4 H2 . . 118.6 no
C4 C5 C6 . . 118.4(3) yes
C4 C5 C7 . 3_665 122.2(2) yes
C6 C5 C7 . 3_665 119.4(2) yes
C5 C6 C7 . . 121.5(2) yes
C5 C6 C12 . . 119.4(3) yes
C7 C6 C12 . . 119.1(2) yes
C5 C7 C6 3_665 . 119.1(2) yes
C5 C7 C8 3_665 . 122.0(2) yes
C6 C7 C8 . . 118.9(2) yes
C7 C8 C9 . . 121.1(2) yes
C7 C8 H3 . . 119.6 no
C9 C8 H3 . . 119.3 no
C8 C9 C10 . . 121.1(2) yes
C8 C9 H4 . . 119.1 no
C10 C9 H4 . . 119.8 no
C9 C10 C11 . . 119.4(2) yes
C9 C10 C12 . . 119.5(2) yes
C11 C10 C12 . . 121.0(2) yes
O2 C11 N1 . . 120.6(2) yes
O2 C11 C10 . . 122.7(3) yes
N1 C11 C10 . . 116.6(2) yes
C2 C12 C6 . . 119.8(2) yes
C2 C12 C10 . . 120.0(3) yes
C6 C12 C10 . . 120.2(2) yes
N2 C13 C14 . . 124.2(2) no
N2 C13 H5 . . 117.9 no
C14 C13 H5 . . 117.9 no
C13 C14 C15 . . 119.1(2) no
C13 C14 H6 . . 120.2 no
C15 C14 H6 . . 120.7 no
C14 C15 C16 . . 117.4(2) no
C14 C15 H7 . . 121.7 no
C16 C15 H7 . . 120.9 no
N1 C16 C15 . . 123.0(2) no
N1 C16 C17 . . 117.6(2) no
C15 C16 C17 . . 119.4(2) no
N2 C17 C16 . . 124.1(2) no
N2 C17 H8 . . 117.4 no
C16 C17 H8 . . 118.5 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
O1 C1 . 1.222(3) yes
O2 C11 . 1.218(3) yes
N1 C1 . 1.414(3) yes
N1 C11 . 1.411(3) yes
N1 C16 . 1.448(3) no
N2 C13 . 1.346(3) no
N2 C17 . 1.335(3) no
C1 C2 . 1.475(3) yes
C2 C3 . 1.381(3) yes
C2 C12 . 1.407(3) yes
C3 C4 . 1.396(3) yes
C3 H1 . 0.95 no
C4 C5 . 1.383(3) yes
C4 H2 . 0.95 no
C5 C6 . 1.433(3) yes
C5 C7 3_665 1.470(3) yes
C6 C7 . 1.431(3) yes
C6 C12 . 1.418(3) yes
C7 C8 . 1.394(3) yes
C8 C9 . 1.393(3) yes
C8 H3 . 0.95 no
C9 C10 . 1.379(3) yes
C9 H4 . 0.95 no
C10 C11 . 1.477(3) yes
C10 C12 . 1.413(3) yes
C13 C14 . 1.383(3) no
C13 H5 . 0.95 no
C14 C15 . 1.393(3) no
C14 H6 . 0.95 no
C15 C16 . 1.379(3) no
C15 H7 . 0.95 no
C16 C17 . 1.392(3) no
C17 H8 . 0.95 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C3 3.057(3) 2_645 no
O1 C17 3.284(3) 1_545 no
O1 C1 3.332(4) 1_545 no
O1 N1 3.340(3) 1_545 no
O1 C4 3.488(3) 2_645 no
O1 C2 3.557(3) 1_545 no
O2 C15 3.221(3) 1_565 no
O2 C15 3.234(3) 3_755 no
O2 O2 3.258(3) 3_765 no
O2 C14 3.365(3) 3_755 no
O2 N1 3.554(3) 1_565 no
N1 C11 3.436(4) 1_545 no
N1 C1 3.598(4) 1_565 no
N2 C14 3.400(4) 1_565 no
N2 C13 3.415(4) 1_565 no
C1 C10 3.507(4) 1_545 no
C1 C11 3.513(4) 1_545 no
C2 C12 3.361(4) 1_545 no
C2 C10 3.548(4) 1_545 no
C2 C6 3.578(4) 1_545 no
C3 C6 3.444(4) 1_545 no
C3 C12 3.508(4) 1_545 no
C3 C5 3.546(4) 1_545 no
C4 C5 3.336(4) 1_545 no
C4 C6 3.518(4) 1_545 no
C4 C7 3.551(4) 3_655 no
C5 C5 3.500(5) 3_655 no
C5 C6 3.579(4) 3_655 no
C6 C7 3.384(4) 1_545 no
C7 C12 3.599(4) 1_565 no
C8 C12 3.527(4) 1_565 no
C9 C10 3.423(4) 1_565 no
C9 C12 3.597(4) 1_565 no
C13 C14 3.529(4) 1_565 no
C14 C17 3.540(4) 1_545 no
C15 C17 3.372(4) 1_545 no
C15 C16 3.428(4) 1_545 no
C16 C17 3.519(4) 1_545 no
