#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/12/2201283.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_2201283
loop_
_publ_author_name
'Çoruh, Ufuk'
'Işık, Şamil'
'Akdemir, Nesuhi'
'Ag̃ar, Erbil'
'Vázquez-López, Ezequiel M.'
'Erdönmez, Ahmet'
_publ_section_title
;
 4,4'-[2,2-Methylenebis(4-chlorophenoxy)]diphthalonitrile
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o953
_journal_page_last               o955
_journal_paper_doi               10.1107/S1600536802013491
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C29 H14 Cl2 N4 O2'
_chemical_formula_moiety         'C29 H14 Cl2 N4 O2'
_chemical_formula_sum            'C29 H14 Cl2 N4 O2'
_chemical_formula_weight         521.34
_chemical_name_systematic
;
4,4'-[2,2-methylenebis(4-chlorophenoxy)]diphthalonitrile
;
_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
_cell_angle_alpha                76.912(2)
_cell_angle_beta                 84.302(2)
_cell_angle_gamma                85.681(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3572(9)
_cell_length_b                   12.1209(13)
_cell_length_c                   12.5925(13)
_cell_measurement_reflns_used    7156
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.67
_cell_volume                     1234.5(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPIII (Farrugia, 1997)'
_computing_publication_material  'PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_device_type  'Bruker CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0809
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7156
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        negligible
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0473
_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)+(0.0416P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2451
_reflns_number_total             4969
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6171.cif
_cod_data_source_block           I
_cod_database_code               2201283
_cod_database_fobs_code          2201283
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl' 0.07649(9) 0.83550(5) 0.88151(6) 0.0731(3) Uani d . 1 . . Cl
Cl -0.31120(11) 1.63056(6) 0.55001(8) 0.1041(3) Uani d . 1 . . Cl
O1' 0.0786(2) 1.32793(13) 0.72180(14) 0.0588(5) Uani d . 1 . . O
O1 -0.37253(19) 1.15562(13) 0.77856(14) 0.0583(5) Uani d . 1 . . O
C12' 0.0718(3) 0.98204(19) 0.8368(2) 0.0478(6) Uani d . 1 . . C
C6 -0.6184(3) 1.02588(19) 0.6191(2) 0.0444(6) Uani d . 1 . . C
C8 -0.4494(3) 1.07922(19) 0.7384(2) 0.0459(6) Uani d . 1 . . C
C9 -0.3640(3) 1.26809(18) 0.7169(2) 0.0478(6) Uani d . 1 . . C
C5 -0.6016(3) 0.91203(19) 0.6755(2) 0.0470(6) Uani d . 1 . . C
C6' -0.1829(3) 1.45322(19) 0.9201(2) 0.0470(6) Uani d . 1 . . C
C3 -0.4339(3) 0.9675(2) 0.7957(2) 0.0532(7) Uani d . 1 . . C
H3 -0.3725 0.9483 0.8555 0.064 Uiso calc R 1 . . H
C14' -0.0165(3) 1.1502(2) 0.7101(2) 0.0442(6) Uani d . 1 . . C
C13' -0.0116(3) 1.0323(2) 0.7488(2) 0.0481(6) Uani d . 1 . . C
H13' -0.0655 0.9878 0.7143 0.058 Uiso calc R 1 . . H
C14 -0.2367(3) 1.29466(19) 0.6388(2) 0.0473(6) Uani d . 1 . . C
C5' -0.1551(3) 1.5672(2) 0.8786(2) 0.0518(7) Uani d . 1 . . C
C4 -0.5097(3) 0.88505(19) 0.7638(2) 0.0556(7) Uani d . 1 . . C
H4 -0.4989 0.8101 0.8023 0.067 Uiso calc R 1 . . H
C8' 0.0010(3) 1.4026(2) 0.7796(2) 0.0498(7) Uani d . 1 . . C
C9' 0.0685(3) 1.2104(2) 0.7651(2) 0.0470(6) Uani d . 1 . . C
C2' -0.2908(4) 1.4216(2) 1.0161(3) 0.0595(8) Uani d . 1 . . C
C7 -0.5408(3) 1.10875(19) 0.6508(2) 0.0455(6) Uani d . 1 . . C
H7 -0.5508 1.1839 0.6129 0.055 Uiso calc R 1 . . H
C11' 0.1534(3) 1.0435(2) 0.8906(2) 0.0550(7) Uani d . 1 . . C
H11' 0.2083 1.0079 0.9509 0.066 Uiso calc R 1 . . H
C7' -0.1056(3) 1.37047(19) 0.8701(2) 0.0475(6) Uani d . 1 . . C
H7' -0.1256 1.2944 0.8974 0.057 Uiso calc R 1 . . H
C4' -0.0473(4) 1.5971(2) 0.7880(3) 0.0668(8) Uani d . 1 . . C
H4' -0.0282 1.6732 0.7597 0.080 Uiso calc R 1 . . H
C13 -0.2275(3) 1.4078(2) 0.5860(2) 0.0560(7) Uani d . 1 . . C
H13 -0.1455 1.4288 0.5311 0.067 Uiso calc R 1 . . H
C1 -0.6808(3) 0.8247(2) 0.6438(2) 0.0598(7) Uani d . 1 . . C
C12 -0.3366(3) 1.4890(2) 0.6129(3) 0.0606(8) Uani d . 1 . . C
C10' 0.1520(3) 1.1602(2) 0.8528(2) 0.0554(7) Uani d . 1 . . C
H10' 0.2077 1.2040 0.8871 0.066 Uiso calc R 1 . . H
C3' 0.0326(3) 1.5155(2) 0.7387(2) 0.0635(8) Uani d . 1 . . C
H3' 0.1068 1.5362 0.6787 0.076 Uiso calc R 1 . . H
C1' -0.2387(3) 1.6519(2) 0.9301(2) 0.0581(7) Uani d . 1 . . C
C2 -0.7170(3) 1.0556(2) 0.5287(3) 0.0524(7) Uani d . 1 . . C
N2 -0.7964(3) 1.0791(2) 0.4574(2) 0.0728(7) Uani d . 1 . . N
N1' -0.3064(3) 1.71836(19) 0.9719(2) 0.0760(7) Uani d . 1 . . N
C10 -0.4748(3) 1.3490(2) 0.7449(2) 0.0625(8) Uani d . 1 . . C
H10 -0.5582 1.3282 0.7988 0.075 Uiso calc R 1 . . H
C15 -0.1097(3) 1.20588(19) 0.6145(2) 0.0536(7) Uani d . 1 . . C
H15A -0.1614 1.1479 0.5904 0.064 Uiso calc R 1 . . H
H15B -0.0349 1.2412 0.5547 0.064 Uiso calc R 1 . . H
C11 -0.4607(3) 1.4612(2) 0.6920(3) 0.0674(8) Uani d . 1 . . C
H11 -0.5343 1.5170 0.7097 0.081 Uiso calc R 1 . . H
N1 -0.7419(3) 0.75420(19) 0.6207(2) 0.0840(8) Uani d . 1 . . N
N2' -0.3741(3) 1.3969(2) 1.0951(2) 0.0824(8) 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C8' O1' C9' 118.94(19) yes
C8 O1 C9 118.8(2) yes
C13' C12' C11' 122.1(2) ?
C13' C12' Cl' 119.2(2) ?
C11' C12' Cl' 118.7(2) ?
C7 C6 C5 120.2(2) ?
C7 C6 C2 120.3(2) ?
C5 C6 C2 119.5(2) ?
C7 C8 O1 124.0(2) ?
C7 C8 C3 120.7(2) ?
O1 C8 C3 115.3(2) ?
C10 C9 C14 122.6(2) ?
C10 C9 O1 118.2(2) ?
C14 C9 O1 118.9(2) ?
C4 C5 C6 118.9(2) ?
C4 C5 C1 120.0(2) ?
C6 C5 C1 121.1(3) ?
C7' C6' C5' 120.7(2) ?
C7' C6' C2' 120.0(2) ?
C5' C6' C2' 119.3(2) ?
C4 C3 C8 119.8(3) ?
C9' C14' C13' 116.2(2) ?
C9' C14' C15 123.0(2) ?
C13' C14' C15 120.8(2) ?
C12' C13' C14' 120.6(2) ?
C9 C14 C13 116.7(2) ?
C9 C14 C15 121.9(2) ?
C13 C14 C15 121.4(2) ?
C4' C5' C6' 119.1(2) ?
C4' C5' C1' 121.0(2) ?
C6' C5' C1' 119.9(3) ?
C3 C4 C5 120.8(2) ?
O1' C8' C7' 123.6(2) ?
O1' C8' C3' 115.4(2) ?
C7' C8' C3' 120.9(2) ?
C10' C9' C14' 123.2(2) ?
C10' C9' O1' 119.1(2) ?
C14' C9' O1' 117.5(2) ?
N2' C2' C6' 177.9(3) ?
C8 C7 C6 119.6(2) ?
C12' C11' C10' 118.3(3) ?
C8' C7' C6' 119.1(2) ?
C5' C4' C3' 120.9(2) ?
C12 C13 C14 121.4(3) ?
N1 C1 C5 178.4(3) ?
C13 C12 C11 121.1(2) ?
C13 C12 Cl 119.2(2) ?
C11 C12 Cl 119.6(2) ?
C9' C10' C11' 119.6(2) ?
C4' C3' C8' 119.4(3) ?
N1' C1' C5' 179.2(3) ?
N2 C2 C6 179.5(3) ?
C9 C10 C11 119.3(3) ?
C14' C15 C14 114.0(2) yes
C12 C11 C10 119.0(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
Cl' C12' . 1.736(2) yes
Cl C12 . 1.738(3) yes
O1' C8' . 1.373(3) yes
O1' C9' . 1.411(3) yes
O1 C8 . 1.376(3) yes
O1 C9 . 1.411(3) yes
C12' C13' . 1.367(3) ?
C12' C11' . 1.370(3) ?
C6 C7 . 1.386(3) ?
C6 C5 . 1.405(3) ?
C6 C2 . 1.435(4) ?
C8 C7 . 1.369(3) ?
C8 C3 . 1.386(3) ?
C9 C10 . 1.377(3) ?
C9 C14 . 1.380(3) ?
C5 C4 . 1.379(3) ?
C5 C1 . 1.438(3) ?
C6' C7' . 1.388(3) ?
C6' C5' . 1.391(3) ?
C6' C2' . 1.431(4) ?
C3 C4 . 1.373(3) ?
C14' C9' . 1.385(3) ?
C14' C13' . 1.400(3) ?
C14' C15 . 1.500(3) ?
C14 C13 . 1.386(3) ?
C14 C15 . 1.514(3) ?
C5' C4' . 1.379(3) ?
C5' C1' . 1.437(3) ?
C8' C7' . 1.376(3) ?
C8' C3' . 1.385(3) ?
C9' C10' . 1.366(3) ?
C2' N2' . 1.150(3) yes
C11' C10' . 1.386(3) ?
C4' C3' . 1.380(3) ?
C13 C12 . 1.368(3) ?
C1 N1 . 1.133(3) yes
C12 C11 . 1.370(4) ?
C1' N1' . 1.145(3) yes
C2 N2 . 1.141(3) yes
C10 C11 . 1.381(3) ?
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
C15 H15A N1 2_476 0.97 2.83 3.246(4) 107 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132255
