#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203194.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
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
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
_symmetry_cell_setting           monoclinic
_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       \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_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+0.001xFc^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_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
_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) ?
_cod_database_code 2203194