#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/32/7203293.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_7203293
loop_
_publ_author_name
'Ofir, Yuval'
'Zelichenok, Alexander'
'Yitzchaik, Shlomo'
_publ_section_title
;
 1,4;5,8-naphthalene-tetracarboxylic diimide derivatives as model
 compounds for molecular layer epitaxy
;
_journal_issue                   22
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              2142
_journal_paper_doi               10.1039/b601258b
_journal_volume                  16
_journal_year                    2006
_chemical_formula_moiety         'C26 H14 N2 O4'
_chemical_formula_sum            'C26 H14 N2 O4'
_chemical_formula_weight         418.39
_chemical_name_systematic
;
?
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.005(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.1360(6)
_cell_length_b                   7.5227(8)
_cell_length_c                   25.623(3)
_cell_measurement_reflns_used    955
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      3.14
_cell_volume                     989.83(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0764
_diffrn_reflns_av_sigmaI/netI    0.0811
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10092
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'Face-Indexed Absorption Correction, Bruker-XPREP'
_exptl_crystal_colour            'light red'
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0644
_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)+(0.0407P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                1116
_reflns_number_total             1952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b601258b.txt
_cod_data_source_block           Diphenyl-NTCDI
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        989.81(19)
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7203293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_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 0.3903(6) 0.1510(4) 0.56216(11) 0.0381(8) Uani 1 1 d . . .
C2 C 0.7453(6) 0.3340(4) 0.60176(12) 0.0398(8) Uani 1 1 d . . .
C3 C 0.7103(5) 0.4645(4) 0.55889(11) 0.0355(7) Uani 1 1 d . . .
C4 C 0.5163(5) 0.4364(4) 0.52018(10) 0.0324(7) Uani 1 1 d . . .
C5 C 0.3571(5) 0.2851(4) 0.52065(11) 0.0351(7) Uani 1 1 d . . .
C6 C 0.8654(6) 0.6123(4) 0.55693(12) 0.0408(8) Uani 1 1 d . . .
H6 H 0.994(5) 0.630(3) 0.5844(10) 0.046(8) Uiso 1 1 d . . .
C7 C 0.1680(6) 0.2617(4) 0.48254(12) 0.0421(8) Uani 1 1 d . . .
H7 H 0.060(6) 0.158(4) 0.4829(11) 0.062(10) Uiso 1 1 d . . .
C8 C 0.5878(6) 0.0679(4) 0.64584(11) 0.0380(8) Uani 1 1 d . . .
C9 C 0.7769(7) -0.0595(5) 0.64824(13) 0.0499(9) Uani 1 1 d . . .
H9 H 0.909(5) -0.064(4) 0.6217(11) 0.059(10) Uiso 1 1 d . . .
C10 C 0.7848(8) -0.1761(5) 0.69001(15) 0.0616(11) Uani 1 1 d . . .
H10 H 0.914(6) -0.261(4) 0.6916(11) 0.059(11) Uiso 1 1 d . . .
C11 C 0.6068(8) -0.1631(5) 0.72904(15) 0.0596(11) Uani 1 1 d . . .
H11 H 0.608(6) -0.238(4) 0.7574(13) 0.069(11) Uiso 1 1 d . . .
C12 C 0.4207(7) -0.0337(5) 0.72630(14) 0.0569(10) Uani 1 1 d . . .
H12 H 0.293(6) -0.020(4) 0.7522(12) 0.070(11) Uiso 1 1 d . . .
C13 C 0.4092(7) 0.0820(5) 0.68468(13) 0.0482(9) Uani 1 1 d . . .
H13 H 0.279(6) 0.170(4) 0.6836(11) 0.059(10) Uiso 1 1 d . . .
N1 N 0.5740(5) 0.1892(3) 0.60207(9) 0.0376(6) Uani 1 1 d . . .
O1 O 0.2659(4) 0.0142(3) 0.56359(8) 0.0548(7) Uani 1 1 d . . .
O2 O 0.9108(4) 0.3501(3) 0.63555(8) 0.0587(7) 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'
O O 0.0106 0.0060 '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
O1 C1 N1 119.8(3) . . ?
O1 C1 C5 123.3(3) . . ?
N1 C1 C5 116.9(3) . . ?
O2 C2 N1 120.5(3) . . ?
O2 C2 C3 122.6(3) . . ?
N1 C2 C3 116.8(3) . . ?
C6 C3 C4 120.0(3) . . ?
C6 C3 C2 120.1(3) . . ?
C4 C3 C2 119.8(3) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 C4 119.6(3) . 3_666 ?
C3 C4 C4 119.0(3) . 3_666 ?
C7 C5 C4 120.2(3) . . ?
C7 C5 C1 119.7(3) . . ?
C4 C5 C1 120.1(3) . . ?
C3 C6 C7 121.0(3) . 3_666 ?
C3 C6 H6 118.2(16) . . ?
C7 C6 H6 120.8(16) 3_666 . ?
C5 C7 C6 120.2(3) . 3_666 ?
C5 C7 H7 119.9(18) . . ?
C6 C7 H7 119.8(18) 3_666 . ?
C9 C8 C13 120.4(3) . . ?
C9 C8 N1 120.2(3) . . ?
C13 C8 N1 119.4(3) . . ?
C8 C9 C10 119.4(4) . . ?
C8 C9 H9 119.9(18) . . ?
C10 C9 H9 120.7(18) . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 121(2) . . ?
C9 C10 H10 119(2) . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 H11 118(2) . . ?
C10 C11 H11 123(2) . . ?
C11 C12 C13 120.7(4) . . ?
C11 C12 H12 122(2) . . ?
C13 C12 H12 117(2) . . ?
C8 C13 C12 119.6(4) . . ?
C8 C13 H13 121.2(19) . . ?
C12 C13 H13 119.2(19) . . ?
C2 N1 C1 124.6(2) . . ?
C2 N1 C8 118.2(2) . . ?
C1 N1 C8 117.2(2) . . ?
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 O1 1.212(3) . ?
C1 N1 1.409(3) . ?
C1 C5 1.474(4) . ?
C2 O2 1.209(3) . ?
C2 N1 1.401(3) . ?
C2 C3 1.482(4) . ?
C3 C6 1.370(4) . ?
C3 C4 1.409(3) . ?
C4 C5 1.402(4) . ?
C4 C4 1.417(5) 3_666 ?
C5 C7 1.376(4) . ?
C6 C7 1.394(4) 3_666 ?
C6 H6 0.96(3) . ?
C7 C6 1.394(4) 3_666 ?
C7 H7 0.96(3) . ?
C8 C9 1.365(4) . ?
C8 C13 1.369(4) . ?
C8 N1 1.446(3) . ?
C9 C10 1.384(4) . ?
C9 H9 0.97(3) . ?
C10 C11 1.370(5) . ?
C10 H10 0.92(3) . ?
C11 C12 1.366(5) . ?
C11 H11 0.92(3) . ?
C12 C13 1.377(4) . ?
C12 H12 0.95(3) . ?
C13 H13 0.94(3) . ?
