#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/25/2202553.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_2202553
loop_
_publ_author_name
'Ocak, Nazan '
'Aǧar, Ayşen'
'Akdemir, Nesuhi'
'Aǧar, Erbil'
'García-Granda, S.'
'Erdönmez, Ahmet'
_publ_section_title
;
 4,4'-(N-Phenyl-2,2'-iminodiethanoxy)diphthalonitrile
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1000
_journal_page_last               o1001
_journal_paper_doi               10.1107/S1600536803013400
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C26 H19 N5 O2'
_chemical_formula_moiety         'C26 H19 N5 O2'
_chemical_formula_sum            'C26 H19 N5 O2'
_chemical_formula_weight         433.46
_chemical_name_systematic
;
 4,4'-(N-Phenyl-2,2'-iminodiethanoxy)diphthalonitrile
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   16.621(5)
_cell_length_b                   9.004(5)
_cell_length_c                   31.494(5)
_cell_measurement_reflns_used    3683
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.52
_cell_measurement_theta_min      0.00
_cell_volume                     4713(3)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2000)'
_computing_data_reduction
'HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0012
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            6338
_diffrn_reflns_theta_full        62.97
_diffrn_reflns_theta_max         62.97
_diffrn_reflns_theta_min         3.87
_diffrn_standards_decay_%        'not measurement'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0507P)²+0.7824P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                1872
_reflns_number_total             3484
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6201.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2202553
_cod_database_fobs_code          2202553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 1.11340(10) 0.54371(19) 0.59502(6) 0.0864(6) Uani d . 1 . . O
N2 0.99288(12) 0.3341(2) 0.62351(7) 0.0787(6) Uani d . 1 . . N
C3 1.00467(14) 0.1828(3) 0.62566(8) 0.0690(7) Uani d . 1 . . C
C4 1.18079(16) 0.5885(3) 0.57522(9) 0.0763(7) Uani d . 1 . . C
C5 1.05667(15) 0.1218(3) 0.65566(9) 0.0852(8) Uani d . 1 . . C
H5 1.0828 0.1838 0.6748 0.102 Uiso calc R 1 . . H
O6 0.85398(11) 0.4874(2) 0.65186(7) 0.1084(7) Uani d . 1 . . O
C7 0.79704(17) 0.6020(3) 0.71028(10) 0.0908(9) Uani d . 1 . . C
H7 0.8484 0.6318 0.7184 0.109 Uiso calc R 1 . . H
C8 1.31338(18) 0.6958(3) 0.53085(10) 0.0880(9) Uani d . 1 . . C
C9 1.03740(17) 0.4346(3) 0.65037(9) 0.0907(9) Uani d . 1 . . C
H9A 1.0406 0.3929 0.6787 0.109 Uiso calc R 1 . . H
H9B 1.0085 0.5279 0.6523 0.109 Uiso calc R 1 . . H
C10 1.12138(16) 0.4644(3) 0.63439(9) 0.0875(8) Uani d . 1 . . C
H10A 1.1511 0.5234 0.6548 0.105 Uiso calc R 1 . . H
H10B 1.1499 0.3718 0.6299 0.105 Uiso calc R 1 . . H
C11 1.16970(17) 0.6789(3) 0.53976(9) 0.0842(8) Uani d . 1 . . C
H11 1.1180 0.7031 0.5309 0.101 Uiso calc R 1 . . H
C12 0.78608(18) 0.5158(3) 0.67405(10) 0.0881(8) Uani d . 1 . . C
C13 1.23535(18) 0.7325(3) 0.51787(9) 0.0843(8) Uani d . 1 . . C
C14 0.65391(17) 0.5975(3) 0.72282(10) 0.0875(8) Uani d . 1 . . C
C15 1.32313(17) 0.6049(4) 0.56557(10) 0.0958(9) Uani d . 1 . . C
H15 1.3748 0.5785 0.5740 0.115 Uiso calc R 1 . . H
C16 1.25782(17) 0.5516(3) 0.58828(9) 0.0891(8) Uani d . 1 . . C
H16 1.2656 0.4918 0.6120 0.107 Uiso calc R 1 . . H
C17 0.64556(17) 0.5084(3) 0.68754(10) 0.0959(9) Uani d . 1 . . C
H17 0.5945 0.4749 0.6801 0.115 Uiso calc R 1 . . H
C18 0.96601(16) 0.0857(4) 0.59793(9) 0.0909(9) Uani d . 1 . . C
H18 0.9301 0.1223 0.5779 0.109 Uiso calc R 1 . . H
C19 0.84996(17) 0.3978(4) 0.61419(10) 0.0999(10) Uani d . 1 . . C
H19A 0.8116 0.4392 0.5942 0.120 Uiso calc R 1 . . H
H19B 0.8336 0.2973 0.6211 0.120 Uiso calc R 1 . . H
C20 0.71044(18) 0.4672(3) 0.66285(10) 0.0939(9) Uani d . 1 . . C
H20 0.7032 0.4077 0.6390 0.113 Uiso calc R 1 . . H
C21 0.73120(18) 0.6426(3) 0.73402(10) 0.0866(8) Uani d . 1 . . C
C22 0.93342(17) 0.3988(3) 0.59559(9) 0.0980(9) Uani d . 1 . . C
H22A 0.9330 0.3441 0.5690 0.118 Uiso calc R 1 . . H
H22B 0.9487 0.5004 0.5893 0.118 Uiso calc R 1 . . H
C23 1.22418(19) 0.8288(4) 0.48186(13) 0.1080(11) Uani d . 1 . . C
C24 1.3821(2) 0.7532(4) 0.50859(11) 0.1144(11) Uani d . 1 . . C
C25 0.74284(19) 0.7335(4) 0.77131(13) 0.1090(11) Uani d . 1 . . C
C26 0.5848(2) 0.6437(4) 0.74660(10) 0.1051(10) Uani d . 1 . . C
C27 1.0698(2) -0.0271(5) 0.65729(14) 0.1229(13) Uani d . 1 . . C
H27 1.1044 -0.0653 0.6778 0.148 Uiso calc R 1 . . H
C28 0.9811(2) -0.0658(5) 0.60024(14) 0.1262(13) Uani d . 1 . . C
H28 0.9554 -0.1303 0.5816 0.151 Uiso calc R 1 . . H
C29 1.0335(3) -0.1208(5) 0.62975(19) 0.1436(18) Uani d . 1 . . C
H29 1.0441 -0.2221 0.6309 0.172 Uiso calc R 1 . . H
N30 1.43768(19) 0.7975(4) 0.49135(10) 0.1578(13) Uani d . 1 . . N
N31 1.21692(18) 0.9059(4) 0.45360(11) 0.1447(13) Uani d . 1 . . N
N32 0.75208(19) 0.8047(4) 0.80074(11) 0.1499(13) Uani d . 1 . . N
N33 0.52887(18) 0.6815(4) 0.76449(10) 0.1413(12) Uani d . 1 . . N
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_publ_flag
C4 O1 C10 118.2(2) yes
C3 N2 C9 121.2(2) yes
C3 N2 C22 121.7(2) yes
C9 N2 C22 117.1(2) yes
N2 C3 C18 121.6(3) ?
N2 C3 C5 120.7(3) ?
C18 C3 C5 117.6(3) ?
O1 C4 C16 124.1(3) ?
O1 C4 C11 115.9(2) ?
C16 C4 C11 120.0(3) ?
C27 C5 C3 120.9(3) ?
C27 C5 H5 119.5 ?
C3 C5 H5 119.5 ?
C12 O6 C19 119.6(2) yes
C21 C7 C12 119.3(3) ?
C21 C7 H7 120.3 ?
C12 C7 H7 120.3 ?
C15 C8 C13 118.8(3) ?
C15 C8 C24 120.6(3) ?
C13 C8 C24 120.6(3) ?
N2 C9 C10 113.0(2) yes
N2 C9 H9A 109.0 ?
C10 C9 H9A 109.0 ?
N2 C9 H9B 109.0 ?
C10 C9 H9B 109.0 ?
H9A C9 H9B 107.8 ?
O1 C10 C9 106.9(2) ?
O1 C10 H10A 110.3 ?
C9 C10 H10A 110.3 ?
O1 C10 H10B 110.3 ?
C9 C10 H10B 110.3 ?
H10A C10 H10B 108.6 ?
C13 C11 C4 120.0(3) ?
C13 C11 H11 120.0 ?
C4 C11 H11 120.0 ?
O6 C12 C20 124.7(3) ?
O6 C12 C7 114.8(3) ?
C20 C12 C7 120.4(3) ?
C11 C13 C8 120.4(3) ?
C11 C13 C23 120.2(3) ?
C8 C13 C23 119.5(3) ?
C17 C14 C21 117.8(3) ?
C17 C14 C26 120.7(3) ?
C21 C14 C26 121.5(3) ?
C8 C15 C16 121.6(3) ?
C8 C15 H15 119.2 ?
C16 C15 H15 119.2 ?
C4 C16 C15 119.2(3) ?
C4 C16 H16 120.4 ?
C15 C16 H16 120.4 ?
C14 C17 C20 122.2(3) ?
C14 C17 H17 118.9 ?
C20 C17 H17 118.9 ?
C28 C18 C3 120.0(3) ?
C28 C18 H18 120.0 ?
C3 C18 H18 120.0 ?
O6 C19 C22 106.0(3) ?
O6 C19 H19A 110.5 ?
C22 C19 H19A 110.5 ?
O6 C19 H19B 110.5 ?
C22 C19 H19B 110.5 ?
H19A C19 H19B 108.7 ?
C12 C20 C17 118.9(3) ?
C12 C20 H20 120.5 ?
C17 C20 H20 120.5 ?
C7 C21 C14 121.3(3) ?
C7 C21 C25 119.1(3) ?
C14 C21 C25 119.6(3) ?
N2 C22 C19 113.0(2) yes
N2 C22 H22A 109.0 ?
C19 C22 H22A 109.0 ?
N2 C22 H22B 109.0 ?
C19 C22 H22B 109.0 ?
H22A C22 H22B 107.8 ?
N31 C23 C13 178.6(4) ?
N30 C24 C8 178.7(5) ?
N32 C25 C21 179.8(5) ?
N33 C26 C14 178.1(4) ?
C29 C27 C5 121.3(4) ?
C29 C27 H27 119.3 ?
C5 C27 H27 119.3 ?
C29 C28 C18 120.4(4) ?
C29 C28 H28 119.8 ?
C18 C28 H28 119.8 ?
C27 C29 C28 119.6(4) ?
C27 C29 H29 120.2 ?
C28 C29 H29 120.2 ?
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 C4 . 1.344(3) yes
O1 C10 . 1.437(3) yes
N2 C3 . 1.378(3) yes
N2 C9 . 1.443(3) yes
N2 C22 . 1.445(3) yes
C3 C18 . 1.393(3) ?
C3 C5 . 1.393(3) ?
C4 C16 . 1.385(3) ?
C4 C11 . 1.394(3) ?
C5 C27 . 1.359(4) ?
C5 H5 . 0.9300 ?
O6 C12 . 1.352(3) yes
O6 C19 . 1.436(3) yes
C7 C21 . 1.375(3) ?
C7 C12 . 1.392(4) ?
C7 H7 . 0.9300 ?
C8 C15 . 1.376(4) ?
C8 C13 . 1.399(4) ?
C8 C24 . 1.436(4) ?
C9 C10 . 1.508(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C13 . 1.378(3) ?
C11 H11 . 0.9300 ?
C12 C20 . 1.377(4) ?
C13 C23 . 1.440(5) ?
C14 C17 . 1.377(4) ?
C14 C21 . 1.393(4) ?
C14 C26 . 1.433(4) ?
C15 C16 . 1.386(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 C20 . 1.380(4) ?
C17 H17 . 0.9300 ?
C18 C28 . 1.389(4) ?
C18 H18 . 0.9300 ?
C19 C22 . 1.506(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20 . 0.9300 ?
C21 C25 . 1.445(5) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 N31 . 1.135(4) yes
C24 N30 . 1.144(4) yes
C25 N32 . 1.137(4) yes
C26 N33 . 1.139(4) yes
C27 C29 . 1.352(5) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.367(5) ?
C28 H28 . 0.9300 ?
C29 H29 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C9 H9B O6 . 0.97 2.59 3.086(4) 112 no
C19 H19A N31 3_466 0.97 2.59 3.546(5) 170 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 N2 C3 C18 -175.6(2)
C22 N2 C3 C18 6.9(4)
C9 N2 C3 C5 3.8(3)
C22 N2 C3 C5 -173.8(2)
C10 O1 C4 C16 6.1(4)
C10 O1 C4 C11 -173.1(2)
N2 C3 C5 C27 -178.6(2)
C18 C3 C5 C27 0.8(4)
C3 N2 C9 C10 79.7(3)
C22 N2 C9 C10 -102.7(3)
C4 O1 C10 C9 177.4(2)
N2 C9 C10 O1 66.2(3)
O1 C4 C11 C13 178.8(2)
C16 C4 C11 C13 -0.5(4)
C19 O6 C12 C20 -1.5(4)
C19 O6 C12 C7 179.2(2)
C21 C7 C12 O6 177.1(2)
C21 C7 C12 C20 -2.3(4)
C4 C11 C13 C8 0.5(4)
C4 C11 C13 C23 -178.5(3)
C15 C8 C13 C11 0.4(4)
C24 C8 C13 C11 -179.0(3)
C15 C8 C13 C23 179.3(3)
C24 C8 C13 C23 0.0(4)
C13 C8 C15 C16 -1.2(4)
C24 C8 C15 C16 178.1(3)
O1 C4 C16 C15 -179.6(2)
C11 C4 C16 C15 -0.4(4)
C8 C15 C16 C4 1.2(4)
C21 C14 C17 C20 -1.9(4)
C26 C14 C17 C20 177.1(3)
N2 C3 C18 C28 178.2(3)
C5 C3 C18 C28 -1.2(4)
C12 O6 C19 C22 175.4(2)
O6 C12 C20 C17 -177.8(3)
C7 C12 C20 C17 1.6(4)
C14 C17 C20 C12 0.5(5)
C12 C7 C21 C14 0.9(4)
C12 C7 C21 C25 -179.3(3)
C17 C14 C21 C7 1.1(4)
C26 C14 C21 C7 -177.8(3)
C17 C14 C21 C25 -178.7(3)
C26 C14 C21 C25 2.3(4)
C3 N2 C22 C19 82.7(3)
C9 N2 C22 C19 -94.9(3)
O6 C19 C22 N2 62.0(3)
C3 C5 C27 C29 0.6(5)
C3 C18 C28 C29 0.3(5)
C5 C27 C29 C28 -1.5(6)
C18 C28 C29 C27 1.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131661
