#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/36/2203696.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_2203696
loop_
_publ_author_name
'Yavuz Köysal'
'Şamil Işık'
'Nesuhi Akdemir'
'Erbil Aǧar'
'Cihan Kantar'
_publ_section_title
;
 4-(3,5-Dimethoxyphenoxy)phthalonitrile
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o930
_journal_page_last               o931
_journal_paper_doi               10.1107/S1600536804010311
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H12 N2 O3'
_chemical_formula_moiety         'C16 H12 N2 O3'
_chemical_formula_sum            'C16 H12 N2 O3'
_chemical_formula_weight         280.28
_chemical_name_systematic
;
4-(3,5-Dimethylphenoxy)phthalonitrile
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 116.331(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8923(12)
_cell_length_b                   7.4816(5)
_cell_length_c                   16.2916(18)
_cell_measurement_reflns_used    9537
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      1.39
_cell_volume                     1408.4(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_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 6.67
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17632
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         1.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.147
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0382
_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)+(0.062P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                2238
_reflns_number_total             3632
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6096.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2203696
_cod_database_fobs_code          2203696
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_type_symbol
C1 0.40434(10) -0.16856(17) -0.45390(8) 0.0471(3) Uani d . 1 C
C2 0.49212(10) -0.17076(19) -0.36571(9) 0.0526(3) Uani d . 1 C
H2 0.4777 -0.1343 -0.3171 0.063 Uiso calc R 1 H
C3 0.60146(10) -0.22728(18) -0.34976(8) 0.0515(3) Uani d . 1 C
H3 0.6604 -0.2304 -0.2902 0.062 Uiso calc R 1 H
C4 0.62384(9) -0.27905(16) -0.42159(8) 0.0446(3) Uani d . 1 C
C5 0.53473(9) -0.27226(15) -0.51109(7) 0.0415(3) Uani d . 1 C
C6 0.42523(9) -0.21732(16) -0.52735(8) 0.0452(3) Uani d . 1 C
H6 0.3661 -0.2130 -0.5868 0.054 Uiso calc R 1 H
C7 0.73690(10) -0.33912(19) -0.40694(9) 0.0553(3) Uani d . 1 C
C8 0.55785(10) -0.32081(18) -0.58661(8) 0.0521(3) Uani d . 1 C
C9 0.24749(10) -0.10729(19) -0.41552(8) 0.0504(3) Uani d . 1 C
C10 0.18105(10) 0.04093(18) -0.42203(9) 0.0512(3) Uani d . 1 C
H10 0.1756 0.1349 -0.4611 0.061 Uiso calc R 1 H
C11 0.12282(10) 0.04528(17) -0.36867(9) 0.0515(3) Uani d . 1 C
C12 0.13113(10) -0.09554(18) -0.31063(9) 0.0516(3) Uani d . 1 C
H12 0.0912 -0.0915 -0.2751 0.062 Uiso calc R 1 H
C13 0.19846(9) -0.24063(17) -0.30587(8) 0.0468(3) Uani d . 1 C
C14 0.25831(10) -0.24898(18) -0.35916(9) 0.0527(3) Uani d . 1 C
H14 0.3039 -0.3472 -0.3565 0.063 Uiso calc R 1 H
C15 0.03583(15) 0.3250(2) -0.43080(12) 0.0739(4) Uani d . 1 C
H15A -0.0137 0.4130 -0.4236 0.111 Uiso calc R 1 H
H15B 0.0001 0.2796 -0.4923 0.111 Uiso calc R 1 H
H15C 0.1088 0.3787 -0.4188 0.111 Uiso calc R 1 H
C16 0.12997(11) -0.4020(2) -0.21398(11) 0.0714(4) Uani d . 1 C
H16A 0.1472 -0.5076 -0.1768 0.107 Uiso calc R 1 H
H16B 0.0531 -0.4105 -0.2629 0.107 Uiso calc R 1 H
H16C 0.1352 -0.2991 -0.1771 0.107 Uiso calc R 1 H
N1 0.82476(10) -0.3869(2) -0.39814(10) 0.0824(4) Uani d . 1 N
N2 0.57813(12) -0.3585(2) -0.64528(9) 0.0809(4) Uani d . 1 N
O1 0.29516(7) -0.10852(16) -0.47769(6) 0.0679(3) Uani d . 1 O
O2 0.05396(10) 0.18266(14) -0.36828(8) 0.0760(3) Uani d . 1 O
O3 0.21116(7) -0.38505(13) -0.25131(7) 0.0619(3) Uani d . 1 O
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_publ_flag
O1 C1 C2 124.61(11) ?
O1 C1 C6 114.43(10) ?
C2 C1 C6 120.80(10) ?
C1 C2 C3 119.79(11) ?
C1 C2 H2 120.1 ?
C3 C2 H2 120.1 ?
C4 C3 C2 120.42(11) ?
C4 C3 H3 119.8 ?
C2 C3 H3 119.8 ?
C3 C4 C5 119.30(10) ?
C3 C4 C7 121.61(11) ?
C5 C4 C7 119.09(11) ?
C6 C5 C4 120.53(10) ?
C6 C5 C8 119.67(10) ?
C4 C5 C8 119.79(10) ?
C5 C6 C1 119.13(10) ?
C5 C6 H6 120.4 ?
C1 C6 H6 120.4 ?
N1 C7 C4 177.96(15) ?
N2 C8 C5 178.78(15) ?
C14 C9 C10 123.41(11) ?
C14 C9 O1 122.28(11) ?
C10 C9 O1 114.07(11) ?
C9 C10 C11 117.71(12) ?
C9 C10 H10 121.1 ?
C11 C10 H10 121.1 ?
O2 C11 C10 124.07(12) ?
O2 C11 C12 115.07(11) ?
C10 C11 C12 120.86(11) ?
C13 C12 C11 119.70(11) ?
C13 C12 H12 120.2 ?
C11 C12 H12 120.2 ?
O3 C13 C12 123.71(11) ?
O3 C13 C14 115.53(10) ?
C12 C13 C14 120.76(11) ?
C9 C14 C13 117.57(11) ?
C9 C14 H14 121.2 ?
C13 C14 H14 121.2 ?
O2 C15 H15A 109.5 ?
O2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
O3 C16 H16A 109.5 ?
O3 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
O3 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C1 O1 C9 121.84(9) yes
C11 O2 C15 117.62(11) yes
C13 O3 C16 116.67(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.3599(13) ?
C1 C2 1.3795(17) ?
C1 C6 1.3869(16) ?
C2 C3 1.3815(17) ?
C2 H2 0.9300 ?
C3 C4 1.3792(17) ?
C3 H3 0.9300 ?
C4 C5 1.4009(16) ?
C4 C7 1.4404(16) ?
C5 C6 1.3785(15) ?
C5 C8 1.4353(16) ?
C6 H6 0.9300 ?
C7 N1 1.1347(16) yes
C8 N2 1.1328(17) yes
C9 C14 1.3685(18) ?
C9 C10 1.3763(17) ?
C9 O1 1.3985(13) yes
C10 C11 1.3781(16) ?
C10 H10 0.9300 ?
C11 O2 1.3601(15) yes
C11 C12 1.3877(18) ?
C12 C13 1.3705(17) ?
C12 H12 0.9300 ?
C13 O3 1.3621(15) yes
C13 C14 1.3954(16) ?
C14 H14 0.9300 ?
C15 O2 1.4196(18) yes
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 O3 1.4304(16) yes
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
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
C2 H2 N2 4_556 0.93 2.51 3.2621(18) 138
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
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.08(13) ?
C6 C1 C2 C3 -2.0(2) ?
C1 C2 C3 C4 0.9(2) ?
C2 C3 C4 C5 0.56(19) ?
C2 C3 C4 C7 -179.79(13) ?
C3 C4 C5 C6 -1.07(18) ?
C7 C4 C5 C6 179.27(12) ?
C3 C4 C5 C8 178.18(12) ?
C7 C4 C5 C8 -1.48(18) ?
C4 C5 C6 C1 0.07(18) ?
C8 C5 C6 C1 -179.18(12) ?
O1 C1 C6 C5 177.04(11) ?
C2 C1 C6 C5 1.45(19) ?
C14 C9 C10 C11 0.0(2) ?
O1 C9 C10 C11 174.53(11) ?
C9 C10 C11 O2 -179.82(13) ?
C9 C10 C11 C12 -0.10(19) ?
O2 C11 C12 C13 -179.97(12) ?
C10 C11 C12 C13 0.3(2) ?
C11 C12 C13 O3 -179.62(12) ?
C11 C12 C13 C14 -0.38(19) ?
C10 C9 C14 C13 -0.09(19) ?
O1 C9 C14 C13 -174.18(11) ?
O3 C13 C14 C9 179.58(11) ?
C12 C13 C14 C9 0.27(18) ?
C2 C1 O1 C9 -25.1(2) ?
C6 C1 O1 C9 159.47(12) ?
C14 C9 O1 C1 -44.36(19) ?
C10 C9 O1 C1 141.04(13) ?
C10 C11 O2 C15 3.9(2) yes
C12 C11 O2 C15 -175.83(13) yes
C12 C13 O3 C16 14.54(18) yes
C14 C13 O3 C16 -164.74(12) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130817
2 PubChem 85778205
