data_2203194
loop_
_publ_author_name
'Petek, Hande'
'I\,s\?ik, \,Samil'
'Akdemir, Nesuhi'
'Kantar, Cihan'
'A\<gar, Erbil'
'\,Senel, \.Ismet'
_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_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
_chemical_melting_point        ?
_chemical_name_common          ?
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 21/n'
_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_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Stoe IPDS-2'
_diffrn_measurement_method     \f
_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_interval_time ?
_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_meas    ?
_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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0862P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1389
_refine_ls_wR_factor_ref       0.1469
_reflns_number_gt              2028
_reflns_number_total           3092
_reflns_threshold_expression   I>2\s(I)
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
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_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 0.0723(14) 0.0825(14) 0.0810(15) 0.0264(12) 0.0274(12) 0.0046(12)
C1 0.0553(13) 0.0562(12) 0.0485(11) 0.0062(10) 0.0170(10) 0.0044(10)
C21 0.107(2) 0.0716(16) 0.0639(16) -0.0314(15) 0.0128(15) -0.0069(13)
C3 0.0441(11) 0.0488(10) 0.0391(10) 0.0042(9) 0.0130(8) 0.0005(8)
C22 0.0795(16) 0.0663(14) 0.0523(13) -0.0198(12) 0.0155(12) 0.0029(11)
C20 0.122(2) 0.0720(16) 0.0614(15) -0.0147(17) 0.0202(16) -0.0162(13)
C8 0.0522(12) 0.0461(11) 0.0399(10) 0.0058(9) 0.0124(9) 0.0092(8)
C9 0.0523(12) 0.0537(12) 0.0495(11) 0.0141(9) 0.0214(9) 0.0217(9)
C23 0.0556(12) 0.0510(11) 0.0367(10) -0.0022(9) 0.0093(9) 0.0096(9)
C19 0.0908(18) 0.0701(15) 0.0477(13) -0.0006(14) 0.0217(12) -0.0069(11)
C10 0.0467(11) 0.0478(11) 0.0371(10) 0.0035(9) 0.0130(8) 0.0107(8)
C18 0.0606(12) 0.0556(12) 0.0353(9) 0.0035(10) 0.0127(9) 0.0033(9)
C11 0.0459(11) 0.0448(10) 0.0360(10) 0.0052(8) 0.0094(8) 0.0087(8)
C17 0.0558(12) 0.0618(12) 0.0395(10) 0.0018(10) 0.0213(9) 0.0041(9)
C12 0.0629(14) 0.0557(12) 0.0467(12) 0.0023(11) 0.0211(10) -0.0016(9)
C16 0.0455(11) 0.0487(11) 0.0396(10) 0.0030(9) 0.0121(8) 0.0092(8)
C13 0.0738(15) 0.0535(13) 0.0615(14) -0.0049(11) 0.0143(12) -0.0088(10)
C15 0.0563(13) 0.0589(12) 0.0544(12) -0.0067(10) 0.0183(10) 0.0061(10)
C14 0.0607(14) 0.0580(13) 0.0721(16) -0.0110(11) 0.0179(12) 0.0025(11)
C2 0.0581(13) 0.0608(13) 0.0495(12) 0.0055(10) 0.0246(10) 0.0057(10)
N2 0.0841(15) 0.0928(15) 0.0676(14) 0.0034(12) 0.0430(12) 0.0123(12)
C4 0.0535(12) 0.0523(11) 0.0395(10) 0.0041(9) 0.0189(9) 0.0039(9)
C7 0.0464(11) 0.0519(11) 0.0375(10) 0.0038(9) 0.0174(8) 0.0050(8)
O1 0.0565(9) 0.0615(9) 0.0434(8) 0.0128(7) 0.0249(6) 0.0175(6)
C5 0.0687(14) 0.0580(12) 0.0521(13) 0.0183(11) 0.0282(11) 0.0204(10)
C6 0.0592(13) 0.0600(13) 0.0548(13) 0.0215(10) 0.0266(10) 0.0174(10)
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_site_symmetry_1
_geom_angle_site_symmetry_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_site_symmetry_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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_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) ?