#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/27/2202787.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_2202787
loop_
_publ_author_name
'Atalay, Şehriman '
'Aǧar, Ayşen'
'Akdemir, Nesuhi'
'Aǧar, Erbil'
_publ_section_title
;
 4-(2-Isopropyl-5-methylphenoxy)phthalonitrile
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1111
_journal_page_last               o1112
_journal_paper_doi               10.1107/S1600536803014685
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C18 H16 N2 O'
_chemical_formula_moiety         'C18 H16 N2 O'
_chemical_formula_sum            'C18 H16 N2 O'
_chemical_formula_weight         276.33
_chemical_name_systematic
;
4-[2-Isopropyl-5-methylphenoxy]phthalonitrile
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.4060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.424(2)
_cell_length_b                   10.2230(12)
_cell_length_c                   13.669(2)
_cell_measurement_reflns_used    15187
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.41
_cell_measurement_theta_min      1.77
_cell_volume                     1559.1(4)
_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_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       '2-circle goniometer'
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14570
_diffrn_reflns_theta_full        29.49
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  30
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tetragonal
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.211
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0621
_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)+(0.1493P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2187
_reflns_number_gt                2185
_reflns_number_total             4223
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6264.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2202787
_cod_database_fobs_code          2202787
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_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
N2 0.6548(3) 0.5094(2) 0.1058(2) 0.1241(10) Uani d . 1 . . N
N1 0.76274(17) 0.34011(18) 0.36416(15) 0.0833(6) Uani d . 1 . . N
C7 0.6179(2) 0.4084(2) 0.11874(17) 0.0826(6) Uani d . 1 . . C
C15 0.2330(5) 0.0914(5) 0.3733(4) 0.194(2) Uani d . 1 . . C
H15A 0.1891 0.0462 0.4155 0.291 Uiso calc R 1 . . H
H15B 0.1858 0.1629 0.3405 0.291 Uiso calc R 1 . . H
H15C 0.3066 0.1244 0.4132 0.291 Uiso calc R 1 . . H
C8 0.69444(15) 0.28661(18) 0.30523(13) 0.0594(4) Uani d . 1 . . C
C1 0.57186(16) 0.28233(18) 0.13556(14) 0.0615(5) Uani d . 1 . . C
C2 0.60824(14) 0.22191(16) 0.22845(12) 0.0530(4) Uani d . 1 . . C
C16 0.2591(2) 0.0027(3) 0.2994(2) 0.0984(8) Uani d . 1 . . C
H16 0.2895 0.0579 0.2518 0.118 Uiso calc R 1 . . H
C6 0.48739(18) 0.2201(2) 0.06171(14) 0.0718(5) Uani d . 1 . . C
H6 0.4624 0.2590 -0.0008 0.086 Uiso calc R 1 . . H
C17 0.1512(3) -0.0643(4) 0.2387(3) 0.1410(14) Uani d . 1 . . C
H17A 0.1233 -0.1292 0.2790 0.211 Uiso calc R 1 . . H
H17B 0.1721 -0.1056 0.1817 0.211 Uiso calc R 1 . . H
H17C 0.0891 -0.0011 0.2163 0.211 Uiso calc R 1 . . H
C3 0.56191(15) 0.10200(17) 0.24792(13) 0.0580(4) Uani d . 1 . . C
H3 0.5869 0.0620 0.3100 0.070 Uiso calc R 1 . . H
C5 0.44112(18) 0.1019(2) 0.08071(14) 0.0707(5) Uani d . 1 . . C
H5 0.3846 0.0608 0.0311 0.085 Uiso calc R 1 . . H
C13 0.3730(2) -0.1582(2) 0.42912(19) 0.0856(7) Uani d . 1 . . C
H13 0.3202 -0.1400 0.4704 0.103 Uiso calc R 1 . . H
C14 0.35844(19) -0.0944(2) 0.33776(17) 0.0744(6) Uani d . 1 . . C
C4 0.47796(16) 0.04311(18) 0.17336(14) 0.0619(5) Uani d . 1 . . C
C12 0.4636(2) -0.2480(2) 0.46065(18) 0.0834(6) Uani d . 1 . . C
H12 0.4700 -0.2889 0.5223 0.100 Uiso calc R 1 . . H
C9 0.44028(18) -0.12750(18) 0.28159(15) 0.0663(5) Uani d . 1 . . C
O1 0.42601(15) -0.07445(14) 0.18432(11) 0.0864(5) Uani d . 1 . . O
C11 0.54423(19) -0.27788(19) 0.40285(17) 0.0740(6) Uani d . 1 . . C
C10 0.52993(19) -0.2153(2) 0.31139(17) 0.0722(5) Uani d . 1 . . C
H10 0.5824 -0.2337 0.2698 0.087 Uiso calc R 1 . . H
C18 0.6433(3) -0.3754(3) 0.4379(3) 0.1084(9) Uani d . 1 . . C
H18A 0.6729 -0.4064 0.3815 0.163 Uiso calc R 1 . . H
H18B 0.6128 -0.4477 0.4697 0.163 Uiso calc R 1 . . H
H18C 0.7072 -0.3341 0.4849 0.163 Uiso calc R 1 . . H
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
N2 C7 C1 179.7(3) yes
C16 C15 H15A 109.5 ?
C16 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C16 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N1 C8 C2 178.3(2) yes
C6 C1 C2 118.89(16) ?
C6 C1 C7 121.16(17) ?
C2 C1 C7 119.91(16) ?
C3 C2 C1 121.12(14) ?
C3 C2 C8 119.85(15) ?
C1 C2 C8 119.03(15) ?
C15 C16 C17 114.2(3) ?
C15 C16 C14 115.1(3) ?
C17 C16 C14 111.0(2) ?
C15 C16 H16 105.1 ?
C17 C16 H16 105.1 ?
C14 C16 H16 105.1 ?
C5 C6 C1 120.19(17) ?
C5 C6 H6 119.9 ?
C1 C6 H6 119.9 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C4 C3 C2 118.60(15) ?
C4 C3 H3 120.7 ?
C2 C3 H3 120.7 ?
C6 C5 C4 120.30(17) ?
C6 C5 H5 119.9 ?
C4 C5 H5 119.9 ?
C12 C13 C14 122.1(2) ?
C12 C13 H13 119.0 ?
C14 C13 H13 119.0 ?
C9 C14 C13 115.02(19) ?
C9 C14 C16 121.2(2) yes
C13 C14 C16 123.8(2) ?
O1 C4 C3 123.64(16) yes
O1 C4 C5 115.46(15) ?
C3 C4 C5 120.90(17) ?
C11 C12 C13 121.3(2) ?
C11 C12 H12 119.3 ?
C13 C12 H12 119.3 ?
C10 C9 C14 123.75(19) ?
C10 C9 O1 117.62(19) yes
C14 C9 O1 118.48(19) ?
C4 O1 C9 118.50(14) yes
C12 C11 C10 117.0(2) ?
C12 C11 C18 121.1(2) ?
C10 C11 C18 121.9(2) ?
C9 C10 C11 120.8(2) ?
C9 C10 H10 119.6 ?
C11 C10 H10 119.6 ?
C11 C18 H18A 109.5 ?
C11 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C11 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
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
N2 C7 . 1.144(3) yes
N1 C8 . 1.134(2) yes
C7 C1 . 1.429(3) yes
C15 C16 . 1.434(5) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C8 C2 . 1.437(2) yes
C1 C6 . 1.392(3) ?
C1 C2 . 1.393(2) ?
C2 C3 . 1.384(2) ?
C16 C17 . 1.496(4) ?
C16 C14 . 1.514(3) yes
C16 H16 . 0.9800 ?
C6 C5 . 1.366(3) ?
C6 H6 . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C3 C4 . 1.379(2) ?
C3 H3 . 0.9300 ?
C5 C4 . 1.383(3) ?
C5 H5 . 0.9300 ?
C13 C12 . 1.381(3) ?
C13 C14 . 1.387(3) ?
C13 H13 . 0.9300 ?
C14 C9 . 1.373(3) ?
C4 O1 . 1.363(2) yes
C12 C11 . 1.371(3) ?
C12 H12 . 0.9300 ?
C9 C10 . 1.357(3) ?
C9 O1 . 1.413(2) yes
C11 C10 . 1.382(3) ?
C11 C18 . 1.507(3) yes
C10 H10 . 0.9300 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 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
C6 C1 C2 C3 0.0(3)
C7 C1 C2 C3 177.68(19)
C6 C1 C2 C8 -179.31(18)
C7 C1 C2 C8 -1.6(3)
C2 C1 C6 C5 0.2(3)
C7 C1 C6 C5 -177.4(2)
C1 C2 C3 C4 -0.3(3)
C8 C2 C3 C4 179.01(17)
C1 C6 C5 C4 -0.1(3)
C12 C13 C14 C9 0.2(3)
C12 C13 C14 C16 178.8(2)
C15 C16 C14 C9 -140.6(4)
C17 C16 C14 C9 87.8(3)
C15 C16 C14 C13 40.8(5)
C17 C16 C14 C13 -90.8(3)
C2 C3 C4 O1 -179.71(18)
C2 C3 C4 C5 0.4(3)
C6 C5 C4 O1 179.9(2)
C6 C5 C4 C3 -0.2(3)
C14 C13 C12 C11 0.3(4)
C13 C14 C9 C10 -0.2(3)
C16 C14 C9 C10 -178.9(2)
C13 C14 C9 O1 175.19(17)
C16 C14 C9 O1 -3.5(3)
C3 C4 O1 C9 12.7(3)
C5 C4 O1 C9 -167.41(19)
C10 C9 O1 C4 -95.7(2)
C14 C9 O1 C4 88.6(2)
C13 C12 C11 C10 -0.7(3)
C13 C12 C11 C18 179.7(2)
C14 C9 C10 C11 -0.2(3)
O1 C9 C10 C11 -175.62(17)
C12 C11 C10 C9 0.6(3)
C18 C11 C10 C9 -179.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 688601
