#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/27/2202707.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_2202707
loop_
_publ_author_name
'Işık, Şamil'
'Köysal, Yavuz'
'Akdemir, Nesuhi'
'Cihan, Kantar'
'Ag̃ar, Erbil'
_publ_section_title
;
 4-(2-Indanoxy)phthalonitrile
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1481
_journal_page_last               o1482
_journal_paper_doi               10.1107/S1600536803019755
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.30
_chemical_name_systematic
;
4-(2-indanoxy)phthalonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.056(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4711(8)
_cell_length_b                   13.4082(8)
_cell_length_c                   11.8736(11)
_cell_measurement_reflns_used    12001
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      1.69
_cell_volume                     1331.8(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), 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 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3702
_diffrn_reflns_theta_full        29.55
_diffrn_reflns_theta_max         29.55
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe & Cie,2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.433
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.216
_refine_ls_extinction_coef       0.040(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.639
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.639
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0491
_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)+(0.0899P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                1467
_reflns_number_total             3702
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6110.cif
_cod_data_source_block           I
_cod_original_cell_volume        1331.82(19)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2202707
_cod_database_fobs_code          2202707
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
H1 0.379(2) 0.1499(13) 0.2896(13) 0.052(5) Uiso d . 1 . . H
O1 0.15215(15) 0.13335(9) 0.30694(11) 0.0610(4) Uani d . 1 . . O
C3 0.2096(2) 0.36134(12) 0.25923(14) 0.0478(4) Uani d . 1 . . C
C15 0.0345(2) -0.02255(12) 0.28340(14) 0.0504(4) Uani d . 1 . . C
H15 -0.0163 -0.0084 0.3455 0.061 Uiso calc R 1 . . H
C8 0.24019(19) 0.35224(12) 0.37710(13) 0.0477(4) Uani d . 1 . . C
C16 -0.0775(2) -0.18986(14) 0.27722(15) 0.0570(5) Uani d . 1 . . C
C4 0.1388(2) 0.44649(13) 0.20891(15) 0.0564(4) Uani d . 1 . . C
H4 0.1177 0.4523 0.1299 0.068 Uiso calc R 1 . . H
C14 0.0120(2) -0.11439(12) 0.22954(14) 0.0498(4) Uani d . 1 . . C
C13 0.0840(2) -0.13464(13) 0.13490(14) 0.0540(4) Uani d . 1 . . C
C10 0.13263(19) 0.04806(13) 0.24465(15) 0.0516(4) Uani d . 1 . . C
C9 0.3201(2) 0.25483(13) 0.41034(14) 0.0569(4) Uani d . 1 . . C
H9A 0.2722 0.2227 0.4699 0.068 Uiso calc R 1 . . H
H9B 0.4333 0.2642 0.4371 0.068 Uiso calc R 1 . . H
C12 0.1782(2) -0.06248(14) 0.09505(15) 0.0622(5) Uani d . 1 . . C
H12 0.2256 -0.0755 0.0310 0.075 Uiso calc R 1 . . H
C5 0.1000(2) 0.52249(14) 0.27710(18) 0.0651(5) Uani d . 1 . . C
H5 0.0532 0.5804 0.2440 0.078 Uiso calc R 1 . . H
C7 0.1994(2) 0.42835(14) 0.44531(15) 0.0596(5) Uani d . 1 . . C
H7 0.2184 0.4225 0.5243 0.072 Uiso calc R 1 . . H
C11 0.2026(2) 0.02861(14) 0.14937(16) 0.0604(5) Uani d . 1 . . C
H11 0.2659 0.0767 0.1219 0.073 Uiso calc R 1 . . H
C1 0.2930(2) 0.19369(14) 0.30129(15) 0.0539(4) Uani d . 1 . . C
C2 0.2632(2) 0.26944(13) 0.20444(14) 0.0549(4) Uani d . 1 . . C
H2A 0.3602 0.2821 0.1730 0.066 Uiso calc R 1 . . H
H2B 0.1810 0.2460 0.1440 0.066 Uiso calc R 1 . . H
C17 0.0670(2) -0.23072(15) 0.08071(15) 0.0638(5) Uani d . 1 . . C
C6 0.1296(2) 0.51368(15) 0.39364(18) 0.0677(5) Uani d . 1 . . C
H6 0.1024 0.5658 0.4386 0.081 Uiso calc R 1 . . H
N1 -0.1454(2) -0.25039(14) 0.31655(15) 0.0803(5) Uani d . 1 . . N
N2 0.0551(3) -0.30699(14) 0.03794(15) 0.0904(6) 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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
C10 O1 C1 118.34(13) yes
C4 C3 C8 120.56(16) ?
C4 C3 C2 129.29(15) ?
C8 C3 C2 110.16(15) ?
C10 C15 C14 119.98(16) ?
C10 C15 H15 120.0 ?
C14 C15 H15 120.0 ?
C7 C8 C3 120.16(16) ?
C7 C8 C9 129.47(15) ?
C3 C8 C9 110.36(14) ?
N1 C16 C14 178.4(2) ?
C5 C4 C3 119.10(17) ?
C5 C4 H4 120.4 ?
C3 C4 H4 120.4 ?
C13 C14 C15 120.10(16) ?
C13 C14 C16 120.60(16) ?
C15 C14 C16 119.17(15) ?
C14 C13 C12 119.39(16) ?
C14 C13 C17 120.82(16) ?
C12 C13 C17 119.75(16) ?
O1 C10 C11 125.01(16) ?
O1 C10 C15 115.00(15) ?
C11 C10 C15 119.99(16) ?
C8 C9 C1 104.19(14) ?
C8 C9 H9A 110.9 ?
C1 C9 H9A 110.9 ?
C8 C9 H9B 110.9 ?
C1 C9 H9B 110.9 ?
H9A C9 H9B 108.9 ?
C11 C12 C13 120.68(17) ?
C11 C12 H12 119.7 ?
C13 C12 H12 119.7 ?
C6 C5 C4 120.53(19) yes
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C8 C7 C6 118.65(17) yes
C8 C7 H7 120.7 ?
C6 C7 H7 120.7 ?
C12 C11 C10 119.81(17) ?
C12 C11 H11 120.1 ?
C10 C11 H11 120.1 ?
O1 C1 C9 106.03(14) ?
O1 C1 C2 111.47(14) ?
C9 C1 C2 105.55(14) ?
O1 C1 H1 108.1(10) ?
C9 C1 H1 115.9(10) ?
C2 C1 H1 109.7(10) ?
C3 C2 C1 104.25(13) ?
C3 C2 H2A 110.9 ?
C1 C2 H2A 110.9 ?
C3 C2 H2B 110.9 ?
C1 C2 H2B 110.9 ?
H2A C2 H2B 108.9 ?
N2 C17 C13 179.3(2) ?
C5 C6 C7 121.00(18) yes
C5 C6 H6 119.5 ?
C7 C6 H6 119.5 ?
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
O1 C10 . 1.358(2) yes
O1 C1 . 1.452(2) yes
C3 C4 . 1.381(2) ?
C3 C8 . 1.388(2) yes
C3 C2 . 1.497(2) yes
C15 C10 . 1.385(2) ?
C15 C14 . 1.387(2) ?
C15 H15 . 0.9300 ?
C8 C7 . 1.380(2) ?
C8 C9 . 1.495(2) yes
C16 N1 . 1.137(2) yes
C16 C14 . 1.434(3) ?
C4 C5 . 1.373(3) ?
C4 H4 . 0.9300 ?
C14 C13 . 1.387(2) ?
C13 C12 . 1.384(2) ?
C13 C17 . 1.437(3) ?
C10 C11 . 1.382(2) ?
C9 C1 . 1.519(2) yes
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C12 C11 . 1.381(3) ?
C12 H12 . 0.9300 ?
C5 C6 . 1.372(3) ?
C5 H5 . 0.9300 ?
C7 C6 . 1.386(3) ?
C7 H7 . 0.9300 ?
C11 H11 . 0.9300 ?
C1 C2 . 1.525(2) yes
C1 H1 . 0.961(18) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C17 N2 . 1.139(2) yes
C6 H6 . 0.9300 ?
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
C4 C3 C8 C7 0.3(2)
C2 C3 C8 C7 -179.59(15)
C4 C3 C8 C9 -178.78(15)
C2 C3 C8 C9 1.37(19)
C8 C3 C4 C5 0.4(3)
C2 C3 C4 C5 -179.74(17)
C10 C15 C14 C13 -1.8(2)
C10 C15 C14 C16 174.15(16)
C15 C14 C13 C12 0.1(3)
C16 C14 C13 C12 -175.87(17)
C15 C14 C13 C17 177.59(16)
C16 C14 C13 C17 1.7(3)
C1 O1 C10 C11 -22.4(2)
C1 O1 C10 C15 157.30(15)
C14 C15 C10 O1 -176.98(14)
C14 C15 C10 C11 2.8(3)
C7 C8 C9 C1 165.72(17)
C3 C8 C9 C1 -15.35(19)
C14 C13 C12 C11 0.8(3)
C17 C13 C12 C11 -176.76(18)
C3 C4 C5 C6 -0.6(3)
C3 C8 C7 C6 -0.7(3)
C9 C8 C7 C6 178.09(17)
C13 C12 C11 C10 0.1(3)
O1 C10 C11 C12 177.80(17)
C15 C10 C11 C12 -1.9(3)
C10 O1 C1 C9 -156.67(15)
C10 O1 C1 C2 88.95(18)
C8 C9 C1 O1 -95.56(15)
C8 C9 C1 C2 22.81(18)
C4 C3 C2 C1 -166.68(17)
C8 C3 C2 C1 13.15(18)
O1 C1 C2 C3 92.60(16)
C9 C1 C2 C3 -22.07(18)
C4 C5 C6 C7 0.1(3)
C8 C7 C6 C5 0.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131422
