#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/30/2203033.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_2203033
loop_
_publ_author_name
'Dinçer, Muharrem'
'Ağar, Ayşen'
'Akdemir, Nesuhi'
'Ağar, Erbil'
'Özdemir, Namık'
_publ_section_title
;
 4-(Benzyloxy)phthalonitrile
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o79
_journal_page_last               o80
_journal_paper_doi               10.1107/S1600536803027764
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H10 N2 O1'
_chemical_formula_moiety         'C15 H10 N2 O'
_chemical_formula_structural     'C15 H10 N2 O1'
_chemical_formula_sum            'C15 H10 N2 O'
_chemical_formula_weight         234.25
_chemical_name_systematic
;
4-(Benzyloxy)phthalonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine-INITIALISE'
_cell_angle_alpha                91.449(11)
_cell_angle_beta                 91.639(11)
_cell_angle_gamma                92.858(11)
_cell_formula_units_Z            2
_cell_length_a                   6.8962(10)
_cell_length_b                   8.8884(11)
_cell_length_c                   9.8343(13)
_cell_measurement_reflns_used    6062
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.07
_cell_volume                     601.59(14)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 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 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8792
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.135
_refine_ls_extinction_coef       0.041(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0394
_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)+(0.0596P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                1487
_reflns_number_total             2247
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6073.cif
_cod_data_source_block           I
_cod_database_code               2203033
_cod_database_fobs_code          2203033
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_occupancy
_atom_site_type_symbol
O1 0.26194(17) 0.71858(11) 0.20727(11) 0.0574(3) Uani d 1 O
N1 0.2368(2) 0.37936(17) 0.80835(16) 0.0733(5) Uani d 1 N
N2 0.2305(3) 0.12313(16) 0.45674(17) 0.0781(5) Uani d 1 N
C1 0.2414(2) 0.42924(17) 0.70252(17) 0.0534(4) Uani d 1 C
C2 0.2470(2) 0.49804(15) 0.57212(15) 0.0461(4) Uani d 1 C
C3 0.2536(2) 0.65466(17) 0.56547(16) 0.0519(4) Uani d 1 C
H3 0.253(2) 0.7124(17) 0.6476(17) 0.056(4) Uiso d 1 H
C4 0.2580(2) 0.72386(17) 0.44293(16) 0.0518(4) Uani d 1 C
H4 0.257(2) 0.833(2) 0.4355(18) 0.065(5) Uiso d 1 H
C5 0.2561(2) 0.63857(15) 0.32196(15) 0.0467(4) Uani d 1 C
C6 0.2490(2) 0.48245(16) 0.32591(16) 0.0494(4) Uani d 1 C
H6 0.250(2) 0.4233(17) 0.2476(18) 0.056(4) Uiso d 1 H
C7 0.2443(2) 0.41297(15) 0.45095(15) 0.0461(4) Uani d 1 C
C8 0.2364(2) 0.25130(17) 0.45428(16) 0.0542(4) Uani d 1 C
C9 0.2583(3) 0.63909(19) 0.07744(17) 0.0609(5) Uani d 1 C
H9A 0.138(3) 0.575(2) 0.0677(19) 0.076(6) Uiso d 1 H
H9B 0.365(3) 0.571(2) 0.078(2) 0.081(6) Uiso d 1 H
C10 0.2791(3) 0.75589(16) -0.02784(15) 0.0559(4) Uani d 1 C
C11 0.1217(4) 0.8282(2) -0.0767(2) 0.0767(6) Uani d 1 C
H11 0.001(3) 0.796(2) -0.0473(19) 0.068(6) Uiso d 1 H
C12 0.1511(6) 0.9444(3) -0.1716(3) 0.0965(9) Uani d 1 C
H12 0.034(4) 0.977(3) -0.188(3) 0.106(8) Uiso d 1 H
C13 0.3347(5) 0.9820(2) -0.2121(2) 0.0914(8) Uani d 1 C
H13 0.362(4) 1.065(3) -0.281(3) 0.121(8) Uiso d 1 H
C14 0.4891(5) 0.9104(2) -0.1647(2) 0.0848(7) Uani d 1 C
H14 0.631(5) 0.948(3) -0.204(3) 0.153(11) Uiso d 1 H
C15 0.4628(3) 0.7980(2) -0.07324(18) 0.0667(5) Uani d 1 C
H15 0.580(3) 0.747(2) -0.032(2) 0.093(7) Uiso d 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
C5 O1 C9 118.97(11) yes
N1 C1 C2 177.62(17) yes
C3 C2 C7 118.61(13) ?
C3 C2 C1 119.35(14) yes
C7 C2 C1 122.04(12) yes
C4 C3 C2 120.87(14) ?
C4 C3 H3 120.5(9) ?
C2 C3 H3 118.6(9) ?
C3 C4 C5 120.41(14) ?
C3 C4 H4 122.3(11) ?
C5 C4 H4 117.2(11) ?
O1 C5 C6 124.86(13) yes
O1 C5 C4 115.34(12) yes
C6 C5 C4 119.80(13) ?
C5 C6 C7 119.43(14) ?
C5 C6 H6 121.7(10) ?
C7 C6 H6 118.9(10) ?
C6 C7 C2 120.89(13) ?
C6 C7 C8 119.14(14) yes
C2 C7 C8 119.98(13) yes
N2 C8 C7 179.8(2) yes
O1 C9 C10 106.52(12) yes
O1 C9 H9A 109.2(11) ?
C10 C9 H9A 114.4(10) ?
O1 C9 H9B 107.7(12) ?
C10 C9 H9B 112.5(12) ?
H9A C9 H9B 106.4(15) ?
C11 C10 C15 118.99(18) ?
C11 C10 C9 121.3(2) ?
C15 C10 C9 119.66(17) ?
C10 C11 C12 119.0(3) ?
C10 C11 H11 117.4(12) ?
C12 C11 H11 123.6(12) ?
C13 C12 C11 119.6(2) ?
C13 C12 H12 135.7(17) ?
C11 C12 H12 104.6(17) ?
C14 C13 C12 121.4(2) ?
C14 C13 H13 116.6(14) ?
C12 C13 H13 122.0(14) ?
C13 C14 C15 119.6(3) ?
C13 C14 H14 115.9(15) ?
C15 C14 H14 124.5(16) ?
C14 C15 C10 121.4(2) ?
C14 C15 H15 120.3(12) ?
C10 C15 H15 118.2(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.3490(17) yes
O1 C9 1.4425(19) yes
N1 C1 1.142(2) yes
N2 C8 1.139(2) yes
C1 C2 1.435(2) yes
C2 C3 1.394(2) ?
C2 C7 1.394(2) ?
C3 C4 1.367(2) ?
C3 H3 0.946(17) ?
C4 C5 1.394(2) ?
C4 H4 0.975(17) ?
C5 C6 1.388(2) ?
C6 C7 1.390(2) ?
C6 H6 0.922(17) ?
C7 C8 1.437(2) yes
C9 C10 1.489(2) ?
C9 H9A 0.985(19) ?
C9 H9B 0.98(2) ?
C10 C11 1.371(3) ?
C10 C15 1.392(3) ?
C11 C12 1.420(4) ?
C11 H11 0.921(19) ?
C12 C13 1.366(4) ?
C12 H12 0.88(3) ?
C13 C14 1.346(4) ?
C13 H13 1.02(3) ?
C14 C15 1.370(3) ?
C14 H14 1.10(3) ?
C15 H15 1.02(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4 N2 1_565 0.975(17) 2.597(18) 3.563(2) 170.4(14)
C3 H3 Cg2 1_556 0.946(17) 2.641(19) 3.586(2) 171.7(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131222
