data_2203218
loop_
_publ_author_name
'Karaday\?i, Nevzat'
'I\;s\?ik, \;Samil'
'Akdemir, Nesuhi'
'A\(gar, Erbil'
'\"Ozil, Musa'
_publ_section_title
;
4-(4-Benzyloxyphenoxy)phthalonitrile
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o254
_journal_page_last             o255
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C21 H14 N2 O2'
_chemical_formula_moiety       'C21 H14 N2 O2'
_chemical_formula_sum          'C21 H14 N2 O2'
_chemical_formula_weight       326.36
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
4-(4-Benzyloxyphenoxy)phthalonitrile
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha              90.00
_cell_angle_beta               81.892(11)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 20.149(3)
_cell_length_b                 10.8606(8)
_cell_length_c                 7.6424(10)
_cell_measurement_reflns_used  4810
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    24.95
_cell_measurement_theta_min    1.87
_cell_volume                   1655.7(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) and PLUTON (Spek, 1997)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device     '2-circle goniometer'
_diffrn_measurement_device_type 'Stoe IPDS-2'
_diffrn_measurement_method     \w
_diffrn_radiation_monochromator 'plane graphite'
_diffrn_radiation_source       'fine-focus sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0713
_diffrn_reflns_av_sigmaI/netI  0.0738
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_l_max     9
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_number          11417
_diffrn_reflns_theta_full      26.00
_diffrn_reflns_theta_max       26.00
_diffrn_reflns_theta_min       2.04
_diffrn_standards_decay_%      none
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.086
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour          colourless
_exptl_crystal_density_diffrn  1.309
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prismatic
_exptl_crystal_F_000           680
_exptl_crystal_size_max        0.42
_exptl_crystal_size_mid        0.31
_exptl_crystal_size_min        0.10
_refine_diff_density_max       0.166
_refine_diff_density_min       -0.152
_refine_ls_extinction_coef     0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   SHELXL97
_refine_ls_goodness_of_fit_ref 0.989
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   227
_refine_ls_number_reflns       3163
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    0.989
_refine_ls_R_factor_all        0.1181
_refine_ls_R_factor_gt         0.0565
_refine_ls_shift/su_max        0.004
_refine_ls_shift/su_mean       0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0862P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1631
_refine_ls_wR_factor_ref       0.1788
_reflns_number_gt              1505
_reflns_number_total           3163
_reflns_threshold_expression   I>2\s(I)
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.78552(18) 0.7370(3) -0.1958(4) 0.0875(11) Uani d . 1 . . N
C20 0.8161(2) 0.6607(4) -0.1425(5) 0.0679(10) Uani d . 1 . . C
C21 0.93288(19) 0.5808(4) -0.3510(6) 0.0808(12) Uani d . 1 . . C
N2 0.9481(2) 0.6322(4) -0.4828(5) 0.1086(13) Uani d . 1 . . N
O2 0.59573(11) 0.35819(19) 0.6401(3) 0.0589(6) Uani d . 1 . . O
O1 0.85714(12) 0.3648(2) 0.3082(3) 0.0721(7) Uani d . 1 . . O
C12 0.76766(17) 0.4684(3) 0.4963(4) 0.0604(9) Uani d . 1 . . C
H12 0.7957 0.5352 0.5074 0.072 Uiso calc R 1 . . H
C10 0.66123(16) 0.3688(3) 0.5659(4) 0.0509(8) Uani d . 1 . . C
C9 0.68610(17) 0.2689(3) 0.4650(4) 0.0589(9) Uani d . 1 . . C
H9 0.6587 0.2009 0.4561 0.071 Uiso calc R 1 . . H
C14 0.49343(16) 0.4253(3) 0.8001(4) 0.0510(8) Uani d . 1 . . C
C11 0.70231(16) 0.4691(3) 0.5829(4) 0.0569(8) Uani d . 1 . . C
H11 0.6862 0.5362 0.6517 0.068 Uiso calc R 1 . . H
C6 0.85448(16) 0.5631(3) -0.0784(4) 0.0585(9) Uani d . 1 . . C
C8 0.75032(17) 0.2686(3) 0.3780(4) 0.0611(9) Uani d . 1 . . C
H8 0.7665 0.2017 0.3088 0.073 Uiso calc R 1 . . H
C15 0.47869(17) 0.3238(3) 0.9097(4) 0.0590(9) Uani d . 1 . . C
H15 0.5132 0.2772 0.9452 0.071 Uiso calc R 1 . . H
C7 0.79091(16) 0.3698(3) 0.3948(4) 0.0572(8) Uani d . 1 . . C
C5 0.83371(16) 0.5107(3) 0.0841(4) 0.0571(9) Uani d . 1 . . C
H5 0.7948 0.5380 0.1532 0.069 Uiso calc R 1 . . H
C19 0.44165(17) 0.4937(3) 0.7532(4) 0.0608(9) Uani d . 1 . . C
H19 0.4509 0.5626 0.6816 0.073 Uiso calc R 1 . . H
C17 0.36162(18) 0.3601(4) 0.9146(5) 0.0677(10) Uani d . 1 . . C
H17 0.3173 0.3371 0.9504 0.081 Uiso calc R 1 . . H
C16 0.41283(19) 0.2922(3) 0.9656(5) 0.0663(10) Uani d . 1 . . C
H16 0.4031 0.2242 1.0387 0.080 Uiso calc R 1 . . H
C13 0.56478(16) 0.4594(3) 0.7404(4) 0.0573(8) Uani d . 1 . . C
H13A 0.5671 0.5331 0.6680 0.069 Uiso calc R 1 . . H
H13B 0.5876 0.4754 0.8416 0.069 Uiso calc R 1 . . H
C4 0.87118(16) 0.4172(3) 0.1437(4) 0.0560(8) Uani d . 1 . . C
C1 0.91191(17) 0.5206(3) -0.1865(4) 0.0622(9) Uani d . 1 . . C
C18 0.37571(19) 0.4615(4) 0.8112(5) 0.0687(10) Uani d . 1 . . C
H18 0.3410 0.5093 0.7795 0.082 Uiso calc R 1 . . H
C2 0.94789(18) 0.4243(4) -0.1249(5) 0.0714(10) Uani d . 1 . . C
H2 0.9860 0.3944 -0.1950 0.086 Uiso calc R 1 . . H
C3 0.92778(17) 0.3727(3) 0.0387(5) 0.0688(10) Uani d . 1 . . C
H3 0.9521 0.3082 0.0785 0.083 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.098(3) 0.078(2) 0.081(2) 0.009(2) 0.0069(19) 0.0184(19)
C20 0.074(2) 0.065(2) 0.059(2) -0.001(2) 0.0130(18) 0.004(2)
C21 0.068(2) 0.092(3) 0.075(3) -0.004(2) 0.016(2) 0.007(2)
N2 0.107(3) 0.126(3) 0.080(2) 0.001(2) 0.029(2) 0.019(2)
O2 0.0583(14) 0.0567(14) 0.0584(13) -0.0062(10) 0.0027(11) -0.0121(11)
O1 0.0570(14) 0.0856(17) 0.0707(16) 0.0069(12) 0.0014(12) 0.0168(14)
C12 0.067(2) 0.057(2) 0.056(2) -0.0100(17) -0.0067(17) 0.0067(17)
C10 0.0563(19) 0.0547(19) 0.0413(16) -0.0038(15) -0.0059(14) 0.0023(15)
C9 0.067(2) 0.0553(19) 0.0518(19) -0.0071(16) 0.0000(16) -0.0062(16)
C14 0.060(2) 0.0482(17) 0.0443(16) 0.0017(15) -0.0045(14) -0.0056(15)
C11 0.061(2) 0.0523(19) 0.057(2) -0.0070(16) -0.0072(16) 0.0015(16)
C6 0.0549(19) 0.056(2) 0.062(2) -0.0034(16) 0.0000(16) -0.0012(17)
C8 0.068(2) 0.060(2) 0.055(2) 0.0034(18) -0.0074(17) -0.0055(17)
C15 0.073(2) 0.0471(18) 0.055(2) 0.0025(16) -0.0025(17) 0.0023(16)
C7 0.0537(19) 0.067(2) 0.0499(18) 0.0016(17) -0.0031(15) 0.0083(17)
C5 0.0553(18) 0.060(2) 0.053(2) -0.0018(16) 0.0056(16) -0.0006(16)
C19 0.073(2) 0.060(2) 0.049(2) 0.0016(18) -0.0097(17) 0.0047(16)
C17 0.061(2) 0.082(3) 0.058(2) -0.006(2) 0.0009(18) -0.010(2)
C16 0.075(2) 0.056(2) 0.063(2) -0.0073(19) 0.0058(19) -0.0005(17)
C13 0.066(2) 0.0502(19) 0.055(2) -0.0019(15) -0.0049(16) -0.0076(16)
C4 0.0533(18) 0.061(2) 0.0513(19) -0.0055(16) 0.0011(15) 0.0004(17)
C1 0.060(2) 0.071(2) 0.051(2) -0.0102(18) 0.0059(17) -0.0057(17)
C18 0.064(2) 0.083(3) 0.061(2) 0.0106(19) -0.0135(18) -0.004(2)
C2 0.057(2) 0.086(3) 0.066(2) 0.0042(19) 0.0099(18) -0.003(2)
C3 0.055(2) 0.068(2) 0.081(3) 0.0037(17) -0.0007(19) 0.000(2)
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'
O O 0.0110 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C20 C6 . . 178.9(4) yes
N2 C21 C1 . . 177.8(5) yes
C10 O2 C13 . . 118.7(2) yes
C4 O1 C7 . . 118.3(3) yes
C7 C12 C11 . . 120.1(3) ?
C7 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
O2 C10 C9 . . 114.7(3) yes
O2 C10 C11 . . 125.6(3) yes
C9 C10 C11 . . 119.7(3) ?
C8 C9 C10 . . 121.1(3) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C19 C14 C15 . . 118.8(3) ?
C19 C14 C13 . . 121.5(3) yes
C15 C14 C13 . . 119.7(3) yes
C10 C11 C12 . . 119.3(3) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C5 C6 C1 . . 121.1(3) ?
C5 C6 C20 . . 120.1(3) ?
C1 C6 C20 . . 118.8(3) ?
C9 C8 C7 . . 118.8(3) ?
C9 C8 H8 . . 120.6 ?
C7 C8 H8 . . 120.6 ?
C16 C15 C14 . . 119.9(3) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C12 C7 C8 . . 121.0(3) ?
C12 C7 O1 . . 121.7(3) yes
C8 C7 O1 . . 117.3(3) yes
C6 C5 C4 . . 119.4(3) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C14 C19 C18 . . 120.7(3) ?
C14 C19 H19 . . 119.6 ?
C18 C19 H19 . . 119.6 ?
C18 C17 C16 . . 119.8(3) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C16 C15 . . 120.6(3) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
O2 C13 C14 . . 107.5(2) yes
O2 C13 H13A . . 110.2 ?
C14 C13 H13A . . 110.2 ?
O2 C13 H13B . . 110.2 ?
C14 C13 H13B . . 110.2 ?
H13A C13 H13B . . 108.5 ?
O1 C4 C5 . . 123.7(3) yes
O1 C4 C3 . . 115.6(3) yes
C5 C4 C3 . . 120.6(3) ?
C2 C1 C6 . . 118.3(3) ?
C2 C1 C21 . . 122.6(3) ?
C6 C1 C21 . . 119.0(3) ?
C17 C18 C19 . . 120.1(3) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C3 C2 C1 . . 120.8(3) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 119.7(3) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
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
N1 C20 . 1.142(5) yes
C20 C6 . 1.438(5) yes
C21 N2 . 1.154(5) yes
C21 C1 . 1.427(5) yes
O2 C10 . 1.366(4) yes
O2 C13 . 1.432(4) yes
O1 C4 . 1.373(4) yes
O1 C7 . 1.405(4) yes
C12 C7 . 1.365(5) ?
C12 C11 . 1.388(5) ?
C12 H12 . 0.9300 ?
C10 C9 . 1.383(4) ?
C10 C11 . 1.385(4) ?
C9 C8 . 1.369(5) ?
C9 H9 . 0.9300 ?
C14 C19 . 1.369(4) ?
C14 C15 . 1.391(4) ?
C14 C13 . 1.492(4) yes
C11 H11 . 0.9300 ?
C6 C5 . 1.377(4) ?
C6 C1 . 1.402(4) ?
C8 C7 . 1.387(5) ?
C8 H8 . 0.9300 ?
C15 C16 . 1.379(5) ?
C15 H15 . 0.9300 ?
C5 C4 . 1.380(4) ?
C5 H5 . 0.9300 ?
C19 C18 . 1.385(5) ?
C19 H19 . 0.9300 ?
C17 C18 . 1.362(5) ?
C17 C16 . 1.369(5) ?
C17 H17 . 0.9300 ?
C16 H16 . 0.9300 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C4 C3 . 1.386(4) ?
C1 C2 . 1.392(5) ?
C18 H18 . 0.9300 ?
C2 C3 . 1.378(5) ?
C2 H2 . 0.9300 ?
C3 H3 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 O2 C10 C9 . . . . -177.3(3) yes
C13 O2 C10 C11 . . . . 2.0(5) ?
O2 C10 C9 C8 . . . . 177.8(3) ?
C11 C10 C9 C8 . . . . -1.5(5) ?
O2 C10 C11 C12 . . . . -178.4(3) ?
C9 C10 C11 C12 . . . . 0.8(5) ?
C7 C12 C11 C10 . . . . 0.3(5) ?
C10 C9 C8 C7 . . . . 1.1(5) ?
C19 C14 C15 C16 . . . . 1.4(5) ?
C13 C14 C15 C16 . . . . 179.8(3) ?
C11 C12 C7 C8 . . . . -0.8(5) ?
C11 C12 C7 O1 . . . . -178.6(3) ?
C9 C8 C7 C12 . . . . 0.1(5) ?
C9 C8 C7 O1 . . . . 178.1(3) ?
C4 O1 C7 C12 . . . . -86.6(4) ?
C4 O1 C7 C8 . . . . 95.4(4) yes
C1 C6 C5 C4 . . . . 2.0(5) ?
C20 C6 C5 C4 . . . . -180.0(3) ?
C15 C14 C19 C18 . . . . -1.0(5) ?
C13 C14 C19 C18 . . . . -179.4(3) ?
C18 C17 C16 C15 . . . . -1.6(5) ?
C14 C15 C16 C17 . . . . -0.1(5) ?
C10 O2 C13 C14 . . . . 178.1(3) yes
C19 C14 C13 O2 . . . . -120.2(3) ?
C15 C14 C13 O2 . . . . 61.5(4) yes
C7 O1 C4 C5 . . . . 24.8(5) ?
C7 O1 C4 C3 . . . . -157.1(3) ?
C6 C5 C4 O1 . . . . 175.5(3) ?
C6 C5 C4 C3 . . . . -2.6(5) ?
C5 C6 C1 C2 . . . . -0.5(5) ?
C20 C6 C1 C2 . . . . -178.6(3) ?
C5 C6 C1 C21 . . . . -177.7(3) ?
C20 C6 C1 C21 . . . . 4.2(5) ?
C16 C17 C18 C19 . . . . 2.0(5) ?
C14 C19 C18 C17 . . . . -0.7(5) ?
C6 C1 C2 C3 . . . . -0.4(5) ?
C21 C1 C2 C3 . . . . 176.7(4) ?
C1 C2 C3 C4 . . . . -0.2(6) ?
O1 C4 C3 C2 . . . . -176.5(3) ?
C5 C4 C3 C2 . . . . 1.7(5) ?