#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/31/2203194.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_2203194
loop_
_publ_author_name
'Petek, Hande'
'Işık, Şamil'
'Akdemir, Nesuhi'
'Kantar, Cihan'
'Aǧar, Erbil'
'Şenel, İsmet'
_publ_section_title
;
 4-(Anthracen-9-ylmethoxy)phthalonitrile
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o256
_journal_page_last               o257
_journal_paper_doi               10.1107/S1600536804000285
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C23 H13 N2 O'
_chemical_formula_moiety         'C23 H13 N2 O'
_chemical_formula_sum            'C23 H13 N2 O'
_chemical_formula_weight         333.35
_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                 97.510(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1396(4)
_cell_length_b                   13.6929(12)
_cell_length_c                   20.4225(13)
_cell_measurement_reflns_used    11824
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.26
_cell_measurement_theta_min      1.79
_cell_volume                     1702.2(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)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       φ
_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  0.1458
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22331
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9437
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.301
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0862P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                2028
_reflns_number_total             3092
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6014.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2203194
_cod_database_fobs_code          2203194
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_type_symbol
N1 1.0046(4) 0.64099(16) 0.07556(12) 0.0771(6) Uani d . 1 N
C1 0.8622(4) 0.68969(16) 0.08563(10) 0.0525(5) Uani d . 1 C
C21 0.2761(5) 0.90677(19) 0.39318(13) 0.0809(8) Uani d . 1 C
H21 0.3841 0.9548 0.3971 0.097 Uiso calc R 1 H
C3 0.6817(3) 0.75153(13) 0.09689(9) 0.0433(5) Uani d . 1 C
C22 0.2769(4) 0.83713(17) 0.34696(11) 0.0654(6) Uani d . 1 C
H22 0.3842 0.8389 0.3188 0.078 Uiso calc R 1 H
C20 0.1146(5) 0.9080(2) 0.43564(14) 0.0845(8) Uani d . 1 C
H20 0.1151 0.9574 0.4669 0.101 Uiso calc R 1 H
C8 0.5527(3) 0.72696(14) 0.14547(9) 0.0455(5) Uani d . 1 C
H8 0.5845 0.6716 0.1713 0.055 Uiso calc R 1 H
C9 0.2861(3) 0.68887(15) 0.24531(10) 0.0505(5) Uani d . 1 C
H9 0.4026 0.6454 0.2455 0.061 Uiso calc R 1 H
C23 0.1186(3) 0.76073(14) 0.33979(9) 0.0475(5) Uani d . 1 C
C19 -0.0421(5) 0.83814(18) 0.43168(11) 0.0684(7) Uani d . 1 C
H19 -0.1499 0.8404 0.4597 0.082 Uiso calc R 1 H
C10 0.1156(3) 0.68723(14) 0.29177(9) 0.0432(5) Uani d . 1 C
C18 -0.0427(4) 0.76077(15) 0.38453(10) 0.0499(5) Uani d . 1 C
C11 -0.0434(3) 0.61240(13) 0.28804(9) 0.0419(5) Uani d . 1 C
C17 -0.1940(4) 0.68573(15) 0.38141(10) 0.0510(5) Uani d . 1 C
H17 -0.2962 0.6850 0.4112 0.061 Uiso calc R 1 H
C12 -0.0640(4) 0.53706(15) 0.23965(11) 0.0539(5) Uani d . 1 C
H12 0.0336 0.5354 0.2084 0.065 Uiso calc R 1 H
C16 -0.1980(3) 0.61125(14) 0.33501(9) 0.0440(5) Uani d . 1 C
C13 -0.2219(4) 0.46762(16) 0.23781(12) 0.0624(6) Uani d . 1 C
H13 -0.2330 0.4202 0.2049 0.075 Uiso calc R 1 H
C15 -0.3573(4) 0.53551(16) 0.33216(11) 0.0555(6) Uani d . 1 C
H15 -0.4548 0.5338 0.3634 0.067 Uiso calc R 1 H
C14 -0.3697(4) 0.46638(17) 0.28527(12) 0.0628(6) Uani d . 1 C
H14 -0.4757 0.4177 0.2840 0.075 Uiso calc R 1 H
C2 0.7703(4) 0.86237(15) 0.00898(11) 0.0546(6) Uani d . 1 C
N2 0.8760(4) 0.88802(17) -0.02967(11) 0.0786(7) Uani d . 1 N
C4 0.6355(3) 0.83461(14) 0.05806(9) 0.0473(5) Uani d . 1 C
C7 0.3762(3) 0.78593(14) 0.15501(9) 0.0442(5) Uani d . 1 C
O1 0.2379(2) 0.76967(10) 0.20030(7) 0.0522(4) Uani d . 1 O
C5 0.4567(4) 0.89194(16) 0.06810(11) 0.0578(6) Uani d . 1 C
H5 0.4234 0.9472 0.0422 0.069 Uiso calc R 1 H
C6 0.3286(4) 0.86781(16) 0.11590(10) 0.0563(6) Uani d . 1 C
H6 0.2088 0.9067 0.1221 0.068 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
N1 C1 C3 178.8(2) ?
C22 C21 C20 120.8(2) ?
C22 C21 H21 119.6 ?
C20 C21 H21 119.6 ?
C8 C3 C4 120.72(17) ?
C8 C3 C1 119.68(17) ?
C4 C3 C1 119.59(17) ?
C21 C22 C23 122.0(2) ?
C21 C22 H22 119.0 ?
C23 C22 H22 119.0 ?
C19 C20 C21 120.7(2) ?
C19 C20 H20 119.6 ?
C21 C20 H20 119.6 ?
C7 C8 C3 119.26(17) ?
C7 C8 H8 120.4 ?
C3 C8 H8 120.4 ?
O1 C9 C10 108.15(15) yes
O1 C9 H9 125.9 ?
C10 C9 H9 125.9 ?
C10 C23 C22 123.07(19) ?
C10 C23 C18 119.93(18) ?
C22 C23 C18 117.00(19) ?
C20 C19 C18 120.2(2) ?
C20 C19 H19 119.9 ?
C18 C19 H19 119.9 ?
C23 C10 C11 120.29(17) yes
C23 C10 C9 118.95(17) yes
C11 C10 C9 120.75(17) ?
C17 C18 C19 121.6(2) ?
C17 C18 C23 119.16(18) ?
C19 C18 C23 119.2(2) ?
C10 C11 C12 124.22(17) ?
C10 C11 C16 119.05(17) ?
C12 C11 C16 116.73(18) ?
C18 C17 C16 121.94(18) ?
C18 C17 H17 119.0 ?
C16 C17 H17 119.0 ?
C13 C12 C11 121.76(19) ?
C13 C12 H12 119.1 ?
C11 C12 H12 119.1 ?
C17 C16 C15 120.92(18) ?
C17 C16 C11 119.55(18) ?
C15 C16 C11 119.50(18) ?
C12 C13 C14 120.7(2) ?
C12 C13 H13 119.6 ?
C14 C13 H13 119.6 ?
C14 C15 C16 121.2(2) ?
C14 C15 H15 119.4 ?
C16 C15 H15 119.4 ?
C15 C14 C13 120.0(2) ?
C15 C14 H14 120.0 ?
C13 C14 H14 120.0 ?
N2 C2 C4 177.5(2) ?
C5 C4 C3 118.96(17) ?
C5 C4 C2 119.62(18) ?
C3 C4 C2 121.41(18) ?
O1 C7 C6 115.04(16) ?
O1 C7 C8 124.92(17) ?
C6 C7 C8 120.03(17) ?
C7 O1 C9 117.79(14) ?
C6 C5 C4 120.50(19) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C5 C6 C7 120.53(18) ?
C5 C6 H6 119.7 ?
C7 C6 H6 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.140(3) ?
C1 C3 1.437(3) ?
C21 C22 1.342(3) ?
C21 C20 1.400(4) ?
C21 H21 0.9300 ?
C3 C8 1.389(3) ?
C3 C4 1.395(3) ?
C22 C23 1.422(3) ?
C22 H22 0.9300 ?
C20 C19 1.351(4) ?
C20 H20 0.9300 ?
C8 C7 1.386(3) ?
C8 H8 0.9300 ?
C9 O1 1.444(2) ?
C9 C10 1.502(3) yes
C9 H9 0.9300 ?
C23 C10 1.404(3) yes
C23 C18 1.432(3) ?
C19 C18 1.431(3) ?
C19 H19 0.9300 ?
C10 C11 1.410(3) yes
C18 C17 1.381(3) ?
C11 C12 1.423(3) ?
C11 C16 1.435(3) ?
C17 C16 1.390(3) ?
C17 H17 0.9300 ?
C12 C13 1.355(3) ?
C12 H12 0.9300 ?
C16 C15 1.422(3) ?
C13 C14 1.412(3) ?
C13 H13 0.9300 ?
C15 C14 1.341(3) ?
C15 H15 0.9300 ?
C14 H14 0.9300 ?
C2 N2 1.141(3) ?
C2 C4 1.432(3) ?
C4 C5 1.386(3) ?
C7 O1 1.353(2) ?
C7 C6 1.385(3) ?
C5 C6 1.372(3) ?
C5 H5 0.9300 ?
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
_geom_torsion_publ_flag
C20 C21 C22 C23 -1.4(4) ?
C22 C21 C20 C19 1.0(5) ?
C4 C3 C8 C7 0.1(3) ?
C1 C3 C8 C7 -178.62(19) ?
C21 C22 C23 C10 179.8(2) ?
C21 C22 C23 C18 -0.3(3) ?
C21 C20 C19 C18 1.0(4) ?
C22 C23 C10 C11 178.80(19) ?
C18 C23 C10 C11 -1.1(3) ?
C22 C23 C10 C9 -0.3(3) yes
C18 C23 C10 C9 179.86(17) ?
O1 C9 C10 C23 -70.9(2) yes
O1 C9 C10 C11 110.05(19) yes
C20 C19 C18 C17 176.8(2) ?
C20 C19 C18 C23 -2.7(4) ?
C10 C23 C18 C17 2.7(3) ?
C22 C23 C18 C17 -177.20(19) ?
C10 C23 C18 C19 -177.82(19) ?
C22 C23 C18 C19 2.3(3) ?
C23 C10 C11 C12 177.64(18) ?
C9 C10 C11 C12 -3.3(3) yes
C23 C10 C11 C16 -1.5(3) ?
C9 C10 C11 C16 177.53(16) ?
C19 C18 C17 C16 178.9(2) ?
C23 C18 C17 C16 -1.6(3) ?
C10 C11 C12 C13 -179.1(2) ?
C16 C11 C12 C13 0.1(3) ?
C18 C17 C16 C15 -179.1(2) ?
C18 C17 C16 C11 -1.0(3) ?
C10 C11 C16 C17 2.6(3) ?
C12 C11 C16 C17 -176.66(18) ?
C10 C11 C16 C15 -179.29(18) ?
C12 C11 C16 C15 1.5(3) ?
C11 C12 C13 C14 -1.5(3) ?
C17 C16 C15 C14 176.3(2) ?
C11 C16 C15 C14 -1.8(3) ?
C16 C15 C14 C13 0.4(4) ?
C12 C13 C14 C15 1.2(4) ?
C8 C3 C4 C5 -0.8(3) ?
C1 C3 C4 C5 178.0(2) ?
C8 C3 C4 C2 178.31(19) ?
C1 C3 C4 C2 -2.9(3) ?
C3 C8 C7 O1 179.63(18) ?
C3 C8 C7 C6 0.6(3) ?
C6 C7 O1 C9 -176.33(18) ?
C8 C7 O1 C9 4.6(3) ?
C10 C9 O1 C7 178.32(16) yes
C3 C4 C5 C6 0.6(3) ?
C2 C4 C5 C6 -178.5(2) ?
C4 C5 C6 C7 0.2(4) ?
O1 C7 C6 C5 -179.9(2) ?
C8 C7 C6 C5 -0.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24732619
