#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/77/2007750.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_2007750
loop_
_publ_author_name
'Mizuguchi, Jin'
_publ_section_title
;
 N,N'-Bis(2-phenethyl)perylene-3,4:9,10-bis(dicarboximide)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1479
_journal_page_last               1481
_journal_paper_doi               10.1107/S0108270198005575
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C40 H26 N2 O4'
_chemical_formula_sum            'C40 H26 N2 O4'
_chemical_formula_weight         598.66
_chemical_name_systematic
;
N,N'-bis(2-phenylethyl)perylene-3,4:9,10-bis(dicarboximide)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 100.270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7370(10)
_cell_length_b                   32.450(3)
_cell_length_c                   9.5070(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.2
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      10.0
_cell_volume                     1438.0(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      298.2
_diffrn_measurement_device       'Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_av_sigmaI/netI    0.076
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3385
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         75
_diffrn_reflns_theta_min         3
_diffrn_standards_decay_%        1.04
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      1.342
_exptl_crystal_density_method    'flotation in benzene/carbontetrachloride'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.22
_refine_ls_extinction_coef       0.01(2)
_refine_ls_extinction_method
'Zachariasen (1967) type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_obs   1.340
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.076
_refine_ls_shift/esd_max         <0.0001
_refine_ls_shift/esd_mean        0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00319|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.109
_reflns_number_observed          1880
_reflns_number_total             3109
_reflns_observed_criterion       I>\s(I)
_cod_data_source_file            oa1058.cif
_cod_data_source_block           oa1058
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00319|Fo|^2^]' 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) + 0.00319|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1438.00(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2007750
_cod_database_fobs_code          2007750
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
O1 -0.5159(6) 0.55823(9) 0.5548(3) 0.0801(9) Uani d . . 1.00
O2 -0.2562(5) 0.65365(7) 0.9012(3) 0.0693(8) Uani d . . 1.00
N1 -0.3963(5) 0.60500(8) 0.7320(3) 0.0533(8) Uani d . . 1.00
C1 0.3110(6) 0.48703(9) 0.8710(3) 0.0405(8) Uani d . . 1.00
C2 0.2763(5) 0.52641(8) 0.9321(3) 0.0381(7) Uani d . . 1.00
C3 0.4606(6) 0.54016(9) 1.0590(3) 0.0406(8) Uani d . . 1.00
C4 0.4181(7) 0.57969(10) 1.1096(4) 0.0507(9) Uani d . . 1.00
C5 0.2018(7) 0.60511(9) 1.0420(4) 0.0513(9) Uani d . . 1.00
C6 0.0161(6) 0.59223(9) 0.9226(3) 0.0449(8) Uani d . . 1.00
C7 0.0528(6) 0.55289(9) 0.8642(3) 0.0413(8) Uani d . . 1.00
C8 -0.1297(6) 0.54001(9) 0.7380(3) 0.0456(8) Uani d . . 1.00
C9 -0.0905(7) 0.50210(10) 0.6802(4) 0.0531(9) Uani d . . 1.00
C10 0.1275(6) 0.47616(10) 0.7453(4) 0.0510(9) Uani d . . 1.00
C11 -0.3610(7) 0.56730(10) 0.6663(4) 0.0534(9) Uani d . . 1.00
C12 -0.2175(7) 0.61991(10) 0.8548(4) 0.0496(9) Uani d . . 1.00
C13 -0.6275(7) 0.63250(10) 0.6603(4) 0.0590(10) Uani d . . 1.00
C14 -0.5243(8) 0.65950(10) 0.5516(5) 0.0780(10) Uani d . . 1.00
C15 -0.7696(8) 0.68330(10) 0.4644(4) 0.0620(10) Uani d . . 1.00
C16 -0.9357(10) 0.6661(2) 0.3469(5) 0.0780(10) Uani d . . 1.00
C17 -1.1450(10) 0.6879(3) 0.2661(5) 0.111(2) Uani d . . 1.00
C18 -1.2050(10) 0.7273(3) 0.3032(8) 0.126(3) Uani d . . 1.00
C19 -1.051(2) 0.7444(2) 0.4216(8) 0.118(2) Uani d . . 1.00
C20 -0.8370(10) 0.72250(10) 0.5028(6) 0.092(2) Uani d . . 1.00
H(4) 0.5415 0.5893 1.1928 0.0611 Uiso calc . . 1.00
H(5) 0.1810 0.6319 1.0789 0.0617 Uiso calc . . 1.00
H(9) -0.2132 0.4935 0.5951 0.0640 Uiso calc . . 1.00
H(10) 0.1522 0.4502 0.7029 0.0613 Uiso calc . . 1.00
H(13a) -0.7825 0.6161 0.6137 0.0714 Uiso calc . . 1.00
H(13b) -0.6911 0.6494 0.7300 0.0714 Uiso calc . . 1.00
H(14a) -0.3873 0.6784 0.5995 0.0940 Uiso calc . . 1.00
H(14b) -0.4375 0.6427 0.4892 0.0940 Uiso calc . . 1.00
H(16) -0.9025 0.6383 0.3222 0.0937 Uiso calc . . 1.00
H(17) -1.2533 0.6759 0.1823 0.1335 Uiso calc . . 1.00
H(18) -1.3534 0.7426 0.2460 0.1516 Uiso calc . . 1.00
H(19) -1.0916 0.7717 0.4486 0.1423 Uiso calc . . 1.00
H(20) -0.7306 0.7345 0.5871 0.1110 Uiso calc . . 1.00
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 7 1
0 1 -5
1 11 2
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 C12 1_555 1_555 1_555 125.0(3) yes
C11 N1 C13 1_555 1_555 1_555 117.3(3) yes
C12 N1 C13 1_555 1_555 1_555 117.6(3) yes
C2 C1 C3 1_555 1_555 3_667 119.0(2) yes
C2 C1 C10 1_555 1_555 1_555 118.6(2) yes
C3 C1 C10 3_667 1_555 1_555 122.5(3) yes
C1 C2 C3 1_555 1_555 1_555 121.8(2) yes
C1 C2 C7 1_555 1_555 1_555 119.0(2) yes
C3 C2 C7 1_555 1_555 1_555 119.1(2) yes
C1 C3 C2 3_667 1_555 1_555 119.2(2) yes
C1 C3 C4 3_667 1_555 1_555 122.5(2) yes
C2 C3 C4 1_555 1_555 1_555 118.3(2) yes
C3 C4 C5 1_555 1_555 1_555 121.8(3) yes
C3 C4 H(4) 1_555 1_555 1_555 119.1(3) no
C5 C4 H(4) 1_555 1_555 1_555 119.1(3) no
C4 C5 C6 1_555 1_555 1_555 121.1(3) yes
C4 C5 H(5) 1_555 1_555 1_555 119.5(3) no
C6 C5 H(5) 1_555 1_555 1_555 119.4(3) no
C5 C6 C7 1_555 1_555 1_555 119.7(3) yes
C5 C6 C12 1_555 1_555 1_555 119.7(3) yes
C7 C6 C12 1_555 1_555 1_555 120.6(3) yes
C2 C7 C6 1_555 1_555 1_555 119.9(2) yes
C2 C7 C8 1_555 1_555 1_555 119.9(3) yes
C6 C7 C8 1_555 1_555 1_555 120.2(3) yes
C7 C8 C9 1_555 1_555 1_555 120.0(3) yes
C7 C8 C11 1_555 1_555 1_555 120.4(3) yes
C9 C8 C11 1_555 1_555 1_555 119.6(3) yes
C8 C9 C10 1_555 1_555 1_555 120.4(3) yes
C8 C9 H(9) 1_555 1_555 1_555 119.8(3) no
C10 C9 H(9) 1_555 1_555 1_555 119.8(3) no
C1 C10 C9 1_555 1_555 1_555 122.0(3) yes
C1 C10 H(10) 1_555 1_555 1_555 119.0(3) no
C9 C10 H(10) 1_555 1_555 1_555 119.0(3) no
O1 C11 N1 1_555 1_555 1_555 120.2(3) yes
O1 C11 C8 1_555 1_555 1_555 122.7(3) yes
N1 C11 C8 1_555 1_555 1_555 117.1(3) yes
O2 C12 N1 1_555 1_555 1_555 120.7(3) yes
O2 C12 C6 1_555 1_555 1_555 122.7(3) yes
N1 C12 C6 1_555 1_555 1_555 116.6(3) yes
N1 C13 C14 1_555 1_555 1_555 111.3(3) yes
N1 C13 H(13a) 1_555 1_555 1_555 109.0(3) no
N1 C13 H(13b) 1_555 1_555 1_555 109.1(3) no
C14 C13 H(13a) 1_555 1_555 1_555 109.0(3) no
C14 C13 H(13b) 1_555 1_555 1_555 109.0(4) no
H(13a) C13 H(13b) 1_555 1_555 1_555 109.5(4) no
C13 C14 C15 1_555 1_555 1_555 111.3(3) yes
C13 C14 H(14a) 1_555 1_555 1_555 109.0(4) no
C13 C14 H(14b) 1_555 1_555 1_555 109.0(4) no
C15 C14 H(14a) 1_555 1_555 1_555 109.0(4) no
C15 C14 H(14b) 1_555 1_555 1_555 109.0(4) no
H(14a) C14 H(14b) 1_555 1_555 1_555 109.5(4) no
C14 C15 C16 1_555 1_555 1_555 120.8(4) yes
C14 C15 C20 1_555 1_555 1_555 121.1(4) yes
C16 C15 C20 1_555 1_555 1_555 118.0(4) yes
C15 C16 C17 1_555 1_555 1_555 120.7(5) yes
C15 C16 H(16) 1_555 1_555 1_555 119.6(4) no
C17 C16 H(16) 1_555 1_555 1_555 119.7(5) no
C16 C17 C18 1_555 1_555 1_555 120.6(5) yes
C16 C17 H(17) 1_555 1_555 1_555 119.8(7) no
C18 C17 H(17) 1_555 1_555 1_555 119.6(6) no
C17 C18 C19 1_555 1_555 1_555 119.7(6) yes
C17 C18 H(18) 1_555 1_555 1_555 120.4(7) no
C19 C18 H(18) 1_555 1_555 1_555 119.9(8) no
C18 C19 C20 1_555 1_555 1_555 119.8(6) yes
C18 C19 H(19) 1_555 1_555 1_555 120.3(7) no
C20 C19 H(19) 1_555 1_555 1_555 119.9(7) no
C15 C20 C19 1_555 1_555 1_555 121.0(5) yes
C15 C20 H(20) 1_555 1_555 1_555 119.4(4) no
C19 C20 H(20) 1_555 1_555 1_555 119.6(5) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1_555 1_555 1.213(4) yes
O2 C12 1_555 1_555 1.206(4) yes
N1 C11 1_555 1_555 1.397(4) yes
N1 C12 1_555 1_555 1.401(4) yes
N1 C13 1_555 1_555 1.479(4) yes
C1 C2 1_555 1_555 1.425(4) yes
C1 C3 1_555 3_667 1.461(4) yes
C1 C10 1_555 1_555 1.392(4) yes
C2 C3 1_555 1_555 1.429(4) yes
C2 C7 1_555 1_555 1.425(4) yes
C3 C4 1_555 1_555 1.397(4) yes
C4 C5 1_555 1_555 1.380(4) yes
C5 C6 1_555 1_555 1.372(4) yes
C6 C7 1_555 1_555 1.415(4) yes
C6 C12 1_555 1_555 1.480(4) yes
C7 C8 1_555 1_555 1.412(4) yes
C8 C9 1_555 1_555 1.374(5) yes
C8 C11 1_555 1_555 1.477(4) yes
C9 C10 1_555 1_555 1.388(4) yes
C13 C14 1_555 1_555 1.503(6) yes
C14 C15 1_555 1_555 1.513(5) yes
C15 C16 1_555 1_555 1.367(6) yes
C15 C20 1_555 1_555 1.375(6) yes
C16 C17 1_555 1_555 1.343(7) yes
C17 C18 1_555 1_555 1.370(10) yes
C18 C19 1_555 1_555 1.350(10) yes
C19 C20 1_555 1_555 1.360(8) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C9 3.289(4) 1_555 3_466
O2 C19 3.446(7) 1_555 4_665
O2 C5 3.479(4) 1_555 1_455
O2 C17 3.592(6) 1_555 1_656
N1 C7 3.526(4) 1_555 1_455
C1 C7 3.541(4) 1_555 3_567
C1 C8 3.575(4) 1_555 1_655
C2 C11 3.557(5) 1_555 1_655
C2 C2 3.561(6) 1_555 3_567
C3 C9 3.558(5) 1_555 3_567
C3 C6 3.562(4) 1_555 1_655
C4 C12 3.472(5) 1_555 1_655
C5 C12 3.566(5) 1_555 1_655
C6 C13 3.505(5) 1_555 1_655
