#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/50/2205003.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_2205003
loop_
_publ_author_name
'Büyükgüngör, Orhan'
'Kos̨ar, Bas̨ak'
'Akdemir, Nesuhi'
'Ağar, Erbil'
'Gümrükçüoğlu, Ismail'
_publ_section_title
;
 4-(2,6-Dimethylphenoxy)phthalonitrile
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o335
_journal_page_last               o336
_journal_paper_doi               10.1107/S1600536805001078
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H12 N2 O'
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_chemical_name_systematic
;
4-(2,6-dimethylphenoxy)phthalonitrile
;
_space_group_IT_number           1
_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                97.921(5)
_cell_angle_beta                 108.234(5)
_cell_angle_gamma                110.548(5)
_cell_formula_units_Z            2
_cell_length_a                   8.160(5)
_cell_length_b                   8.451(5)
_cell_length_c                   11.629(5)
_cell_measurement_reflns_used    10590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.325
_cell_measurement_theta_min      1.915
_cell_volume                     685.0(7)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1998)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9887
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0388
_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)+(0.0767P)²+0.0109P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2415
_reflns_number_total             2681
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6581.cif
_cod_data_source_block           I
_cod_database_code               2205003
loop_
_symmetry_equiv_pos_as_xyz
'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_type_symbol
C1B 0.1708(3) 0.3762(3) 0.9003(2) 0.0610(5) Uani d . 1 C
C1A 0.3880(3) 0.6632(3) 0.4943(2) 0.0573(4) Uani d . 1 C
C2B 0.1452(3) 0.2139(3) 0.9215(2) 0.0627(5) Uani d . 1 C
H2B 0.1695 0.1342 0.8735 0.075 Uiso calc R 1 H
C2A 0.5702(3) 0.7344(3) 0.5856(2) 0.0680(6) Uani d . 1 C
H2A 0.6711 0.7362 0.5639 0.082 Uiso calc R 1 H
C3B 0.0824(3) 0.1724(3) 1.0163(2) 0.0595(5) Uani d . 1 C
C3A 0.6013(3) 0.8026(4) 0.7087(2) 0.0757(7) Uani d . 1 C
H3A 0.7238 0.8495 0.7703 0.091 Uiso calc R 1 H
C4B 0.0456(3) 0.2921(3) 1.08783(19) 0.0592(5) Uani d . 1 C
C4A 0.4526(3) 0.8026(3) 0.7424(2) 0.0676(5) Uani d . 1 C
C5B 0.0727(3) 0.4532(3) 1.0641(2) 0.0659(5) Uani d . 1 C
H5B 0.0490 0.5336 1.1120 0.079 Uiso calc R 1 H
C5A 0.2698(3) 0.7272(3) 0.6499(2) 0.0633(5) Uani d . 1 C
C6B 0.1340(3) 0.4958(3) 0.9708(2) 0.0664(5) Uani d . 1 C
H6B 0.1507 0.6041 0.9550 0.080 Uiso calc R 1 H
C6A 0.2370(3) 0.6565(3) 0.5266(2) 0.0632(5) Uani d . 1 C
H6A 0.1139 0.6046 0.4654 0.076 Uiso calc R 1 H
C7B 0.0554(4) 0.0043(3) 1.0398(2) 0.0690(6) Uani d . 1 C
C7A 0.4871(5) 0.8840(5) 0.8687(3) 0.0911(8) Uani d . 1 C
C8B -0.0185(3) 0.2510(3) 1.1868(2) 0.0676(5) Uani d . 1 C
C8A 0.1154(4) 0.7293(5) 0.6828(3) 0.0835(7) Uani d . 1 C
C9B 0.2681(4) 0.3169(3) 0.7332(2) 0.0650(5) Uani d . 1 C
C9A 0.4920(3) 0.6146(3) 0.32842(19) 0.0591(5) Uani d . 1 C
C10B 0.1243(5) 0.2081(4) 0.6205(3) 0.0874(8) Uani d . 1 C
C10A 0.5608(4) 0.4875(4) 0.3310(3) 0.0765(6) Uani d . 1 C
C11B 0.1756(11) 0.1058(5) 0.5450(4) 0.135(2) Uani d . 1 C
H11B 0.0865 0.0294 0.4670 0.161 Uiso calc R 1 H
C11A 0.7003(5) 0.5048(5) 0.2842(4) 0.0998(10) Uani d . 1 C
H11A 0.7498 0.4211 0.2844 0.120 Uiso calc R 1 H
C12B 0.3645(15) 0.1199(8) 0.5884(8) 0.155(3) Uani d . 1 C
H12B 0.3977 0.0504 0.5390 0.187 Uiso calc R 1 H
C12A 0.7660(5) 0.6420(6) 0.2379(4) 0.1020(10) Uani d . 1 C
H12A 0.8613 0.6518 0.2080 0.122 Uiso calc R 1 H
C13B 0.4938(10) 0.2301(8) 0.6977(7) 0.136(2) Uani d . 1 C
H13B 0.6171 0.2383 0.7232 0.163 Uiso calc R 1 H
C13A 0.6947(4) 0.7658(4) 0.2344(3) 0.0886(8) Uani d . 1 C
H13A 0.7399 0.8576 0.2008 0.106 Uiso calc R 1 H
C14B 0.4514(5) 0.3304(5) 0.7728(4) 0.0940(9) Uani d . 1 C
C14A 0.5546(3) 0.7554(3) 0.2810(2) 0.0657(5) Uani d . 1 C
C15B -0.0685(6) 0.2034(7) 0.5815(4) 0.1346(18) Uani d . 1 C
H15A -0.1495 0.1060 0.6005 0.202 Uiso calc R 1 H
H15B -0.1190 0.1899 0.4925 0.202 Uiso calc R 1 H
H15C -0.0621 0.3111 0.6262 0.202 Uiso calc R 1 H
C15A 0.4856(7) 0.3374(5) 0.3833(5) 0.1179(13) Uani d . 1 C
H15D 0.5566 0.3712 0.4726 0.177 Uiso calc R 1 H
H15E 0.4982 0.2371 0.3440 0.177 Uiso calc R 1 H
H15F 0.3540 0.3080 0.3668 0.177 Uiso calc R 1 H
C16B 0.6007(7) 0.4559(9) 0.8976(6) 0.1441(18) Uani d . 1 C
H16A 0.6018 0.3967 0.9624 0.216 Uiso calc R 1 H
H16B 0.5723 0.5548 0.9174 0.216 Uiso calc R 1 H
H16C 0.7231 0.4961 0.8924 0.216 Uiso calc R 1 H
C16A 0.4764(5) 0.8899(4) 0.2778(3) 0.0895(8) Uani d . 1 C
H16D 0.3409 0.8330 0.2516 0.134 Uiso calc R 1 H
H16E 0.5065 0.9533 0.2194 0.134 Uiso calc R 1 H
H16F 0.5311 0.9703 0.3604 0.134 Uiso calc R 1 H
N1B 0.0319(5) -0.1293(4) 1.0571(3) 0.0961(8) Uani d . 1 N
N1A 0.5133(7) 0.9508(7) 0.9684(3) 0.1353(14) Uani d . 1 N
N2B -0.0676(4) 0.2231(4) 1.2660(3) 0.0881(6) Uani d . 1 N
N2A -0.0024(5) 0.7378(7) 0.7127(4) 0.1277(14) Uani d . 1 N
O1B 0.2304(3) 0.4304(2) 0.80915(16) 0.0739(4) Uani d . 1 O
O1A 0.3439(2) 0.5978(2) 0.36961(14) 0.0688(4) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
O1B C1B C2B 123.61(19) ?
O1B C1B C6B 115.2(2) ?
C2B C1B C6B 121.2(2) ?
O1A C1A C2A 123.90(19) ?
O1A C1A C6A 115.71(18) ?
C2A C1A C6A 120.4(2) ?
C1B C2B C3B 118.62(19) ?
C1B C2B H2B 120.7 ?
C3B C2B H2B 120.7 ?
C3A C2A C1A 119.6(2) ?
C3A C2A H2A 120.2 ?
C1A C2A H2A 120.2 ?
C2B C3B C4B 120.5(2) ?
C2B C3B C7B 119.3(2) ?
C4B C3B C7B 120.2(2) ?
C2A C3A C4A 120.9(2) ?
C2A C3A H3A 119.5 ?
C4A C3A H3A 119.5 ?
C5B C4B C3B 119.40(19) ?
C5B C4B C8B 119.59(19) ?
C3B C4B C8B 121.0(2) ?
C3A C4A C5A 118.7(2) ?
C3A C4A C7A 120.8(2) ?
C5A C4A C7A 120.4(2) ?
C6B C5B C4B 120.8(2) ?
C6B C5B H5B 119.6 ?
C4B C5B H5B 119.6 ?
C6A C5A C4A 120.7(2) ?
C6A C5A C8A 119.9(2) ?
C4A C5A C8A 119.4(2) ?
C5B C6B C1B 119.5(2) ?
C5B C6B H6B 120.3 ?
C1B C6B H6B 120.3 ?
C5A C6A C1A 119.6(2) ?
C5A C6A H6A 120.2 ?
C1A C6A H6A 120.2 ?
N1B C7B C3B 179.1(3) yes
N1A C7A C4A 178.8(4) yes
N2B C8B C4B 178.2(3) yes
N2A C8A C5A 177.0(4) yes
C10B C9B C14B 124.5(3) ?
C10B C9B O1B 118.1(3) ?
C14B C9B O1B 117.3(3) ?
C10A C9A C14A 123.3(2) ?
C10A C9A O1A 119.1(2) ?
C14A C9A O1A 117.46(19) ?
C9B C10B C11B 115.0(4) ?
C9B C10B C15B 122.0(3) ?
C11B C10B C15B 123.0(4) ?
C9A C10A C11A 117.3(3) ?
C9A C10A C15A 120.5(3) ?
C11A C10A C15A 122.2(3) ?
C10B C11B C12B 119.5(5) ?
C10B C11B H11B 120.2 ?
C12B C11B H11B 120.2 ?
C12A C11A C10A 120.9(3) ?
C12A C11A H11A 119.5 ?
C10A C11A H11A 119.5 ?
C13B C12B C11B 121.0(4) ?
C13B C12B H12B 119.5 ?
C11B C12B H12B 119.5 ?
C11A C12A C13A 121.2(3) ?
C11A C12A H12A 119.4 ?
C13A C12A H12A 119.4 ?
C12B C13B C14B 121.5(6) ?
C12B C13B H13B 119.2 ?
C14B C13B H13B 119.2 ?
C12A C13A C14A 120.3(3) ?
C12A C13A H13A 119.8 ?
C14A C13A H13A 119.8 ?
C13B C14B C9B 118.4(5) ?
C13B C14B C16B 120.9(5) ?
C9B C14B C16B 120.7(4) ?
C9A C14A C13A 117.0(2) ?
C9A C14A C16A 122.3(2) ?
C13A C14A C16A 120.7(3) ?
C10B C15B H15A 109.5 ?
C10B C15B H15B 109.5 ?
H15A C15B H15B 109.5 ?
C10B C15B H15C 109.5 ?
H15A C15B H15C 109.5 ?
H15B C15B H15C 109.5 ?
C10A C15A H15D 109.5 ?
C10A C15A H15E 109.5 ?
H15D C15A H15E 109.5 ?
C10A C15A H15F 109.5 ?
H15D C15A H15F 109.5 ?
H15E C15A H15F 109.5 ?
C14B C16B H16A 109.5 ?
C14B C16B H16B 109.5 ?
H16A C16B H16B 109.5 ?
C14B C16B H16C 109.5 ?
H16A C16B H16C 109.5 ?
H16B C16B H16C 109.5 ?
C14A C16A H16D 109.5 ?
C14A C16A H16E 109.5 ?
H16D C16A H16E 109.5 ?
C14A C16A H16F 109.5 ?
H16D C16A H16F 109.5 ?
H16E C16A H16F 109.5 ?
C1B O1B C9B 118.67(18) ?
C1A O1A C9A 118.77(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1B O1B 1.367(3) yes
C1B C2B 1.382(3) ?
C1B C6B 1.387(3) ?
C1A O1A 1.360(3) yes
C1A C2A 1.381(3) ?
C1A C6A 1.382(3) yes
C2B C3B 1.391(3) ?
C2B H2B 0.9300 ?
C2A C3A 1.375(4) ?
C2A H2A 0.9300 ?
C3B C4B 1.394(3) ?
C3B C7B 1.437(3) ?
C3A C4A 1.386(3) ?
C3A H3A 0.9300 ?
C4B C5B 1.382(3) ?
C4B C8B 1.441(3) ?
C4A C5A 1.389(3) ?
C4A C7A 1.428(4) ?
C5B C6B 1.370(3) ?
C5B H5B 0.9300 ?
C5A C6A 1.377(3) ?
C5A C8A 1.432(3) ?
C6B H6B 0.9300 ?
C6A H6A 0.9300 ?
C7B N1B 1.134(4) yes
C7A N1A 1.134(5) yes
C8B N2B 1.136(3) yes
C8A N2A 1.140(4) yes
C9B C10B 1.374(4) ?
C9B C14B 1.377(4) ?
C9B O1B 1.392(3) yes
C9A C10A 1.375(3) ?
C9A C14A 1.382(3) ?
C9A O1A 1.404(3) yes
C10B C11B 1.403(6) ?
C10B C15B 1.479(6) ?
C10A C11A 1.380(5) ?
C10A C15A 1.502(5) ?
C11B C12B 1.418(10) ?
C11B H11B 0.9300 ?
C11A C12A 1.355(6) ?
C11A H11A 0.9300 ?
C12B C13B 1.320(11) ?
C12B H12B 0.9300 ?
C12A C13A 1.363(6) ?
C12A H12A 0.9300 ?
C13B C14B 1.338(6) ?
C13B H13B 0.9300 ?
C13A C14A 1.392(4) ?
C13A H13A 0.9300 ?
C14B C16B 1.510(7) ?
C14A C16A 1.485(4) ?
C15B H15A 0.9600 ?
C15B H15B 0.9600 ?
C15B H15C 0.9600 ?
C15A H15D 0.9600 ?
C15A H15E 0.9600 ?
C15A H15F 0.9600 ?
C16B H16A 0.9600 ?
C16B H16B 0.9600 ?
C16B H16C 0.9600 ?
C16A H16D 0.9600 ?
C16A H16E 0.9600 ?
C16A H16F 0.9600 ?
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
O1B C1B C2B C3B -179.5(2)
C6B C1B C2B C3B -0.4(3)
O1A C1A C2A C3A 177.8(2)
C6A C1A C2A C3A -1.5(4)
C1B C2B C3B C4B 0.2(3)
C1B C2B C3B C7B -179.9(2)
C1A C2A C3A C4A -0.6(4)
C2B C3B C4B C5B -0.2(3)
C7B C3B C4B C5B 179.9(2)
C2B C3B C4B C8B -179.6(2)
C7B C3B C4B C8B 0.4(3)
C2A C3A C4A C5A 2.0(4)
C2A C3A C4A C7A -175.8(3)
C3B C4B C5B C6B 0.4(3)
C8B C4B C5B C6B 179.8(2)
C3A C4A C5A C6A -1.1(4)
C7A C4A C5A C6A 176.6(3)
C3A C4A C5A C8A -178.8(3)
C7A C4A C5A C8A -1.0(4)
C4B C5B C6B C1B -0.6(4)
O1B C1B C6B C5B 179.7(2)
C2B C1B C6B C5B 0.6(4)
C4A C5A C6A C1A -1.0(4)
C8A C5A C6A C1A 176.6(2)
O1A C1A C6A C5A -177.1(2)
C2A C1A C6A C5A 2.3(3)
C2B C3B C7B N1B -83(19)
C4B C3B C7B N1B 97(19)
C3A C4A C7A N1A 11E1(2)
C5A C4A C7A N1A -6E1(2)
C5B C4B C8B N2B -18(9)
C3B C4B C8B N2B 162(9)
C6A C5A C8A N2A -144(6)
C4A C5A C8A N2A 34(6)
C14B C9B C10B C11B 0.5(4)
O1B C9B C10B C11B 175.9(2)
C14B C9B C10B C15B -178.1(3)
O1B C9B C10B C15B -2.8(4)
C14A C9A C10A C11A 0.5(4)
O1A C9A C10A C11A 177.0(2)
C14A C9A C10A C15A -179.7(3)
O1A C9A C10A C15A -3.1(4)
C9B C10B C11B C12B 0.4(4)
C15B C10B C11B C12B 179.0(3)
C9A C10A C11A C12A 0.1(5)
C15A C10A C11A C12A -179.8(4)
C10B C11B C12B C13B -1.3(6)
C10A C11A C12A C13A -1.0(6)
C11B C12B C13B C14B 1.2(7)
C11A C12A C13A C14A 1.3(5)
C12B C13B C14B C9B -0.2(6)
C12B C13B C14B C16B -180.0(4)
C10B C9B C14B C13B -0.7(4)
O1B C9B C14B C13B -176.0(3)
C10B C9B C14B C16B 179.1(3)
O1B C9B C14B C16B 3.7(4)
C10A C9A C14A C13A -0.1(3)
O1A C9A C14A C13A -176.8(2)
C10A C9A C14A C16A 179.2(3)
O1A C9A C14A C16A 2.6(3)
C12A C13A C14A C9A -0.7(4)
C12A C13A C14A C16A 179.9(3)
C2B C1B O1B C9B -0.1(3)
C6B C1B O1B C9B -179.2(2)
C10B C9B O1B C1B 93.1(3)
C14B C9B O1B C1B -91.2(3)
C2A C1A O1A C9A -5.0(3)
C6A C1A O1A C9A 174.35(19)
C10A C9A O1A C1A 87.1(3)
C14A C9A O1A C1A -96.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 827492
