#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/11/2221103.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_2221103
loop_
_publ_author_name
'Hanif, Muhammad'
'Rafiq, Muhammad'
'Saleem, Muhammad'
'Qadeer, Ghulam'
'Wong, Wai-Yeung'
_publ_section_title
;
 4-Benzyloxy-3-methoxybenzonitrile
;
_journal_coeditor_code           HK2626
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o572
_journal_paper_doi               10.1107/S1600536809005613
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 N O2'
_chemical_formula_moiety         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.26
_chemical_name_common            411.0(10)
_chemical_name_systematic
;
4-Benzyloxy-3-methoxybenzonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.663(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9434(12)
_cell_length_b                   9.5469(8)
_cell_length_c                   8.8522(7)
_cell_measurement_reflns_used    7856
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.60
_cell_volume                     1232.16(17)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and 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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7286
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0375
_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)+(0.0606P)²+0.2089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                2499
_reflns_number_total             2983
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2626.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221103
_cod_database_fobs_code          2221103
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_type_symbol
_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
O O1 0.26381(5) 0.56473(9) 0.00751(9) 0.0409(2) Uani d . 1 . .
O O2 0.26362(5) 0.38653(9) 0.22449(9) 0.0423(2) Uani d . 1 . .
N N1 -0.09205(7) 0.55876(14) 0.35630(13) 0.0545(3) Uani d . 1 . .
C C1 0.44027(9) 0.66914(15) -0.09352(15) 0.0492(3) Uani d . 1 . .
H H1A 0.4473 0.7296 -0.0065 0.059 Uiso calc R 1 . .
C C2 0.51719(9) 0.62309(16) -0.14277(16) 0.0520(3) Uani d . 1 . .
H H2A 0.5765 0.6523 -0.0893 0.062 Uiso calc R 1 . .
C C3 0.50825(9) 0.53599(14) -0.26781(15) 0.0479(3) Uani d . 1 . .
H H3A 0.5612 0.5033 -0.3000 0.058 Uiso calc R 1 . .
C C4 0.42195(9) 0.49571(15) -0.34716(16) 0.0510(3) Uani d . 1 . .
H H4A 0.4155 0.4364 -0.4351 0.061 Uiso calc R 1 . .
C C5 0.34464(8) 0.54158(13) -0.29886(14) 0.0440(3) Uani d . 1 . .
H H5A 0.2855 0.5137 -0.3543 0.053 Uiso calc R 1 . .
C C6 0.35295(8) 0.62749(12) -0.17068(13) 0.0375(2) Uani d . 1 . .
C C7 0.26977(8) 0.66610(13) -0.11153(14) 0.0425(3) Uani d . 1 . .
H H7A 0.2760 0.7620 -0.0680 0.051 Uiso calc R 1 . .
H H7B 0.2141 0.6623 -0.1961 0.051 Uiso calc R 1 . .
C C8 0.18984(7) 0.57131(11) 0.07225(12) 0.0339(2) Uani d . 1 . .
C C9 0.18915(7) 0.47256(11) 0.19135(12) 0.0328(2) Uani d . 1 . .
C C10 0.11690(7) 0.46987(12) 0.26518(12) 0.0343(2) Uani d . 1 . .
H H10A 0.1166 0.4048 0.3462 0.041 Uiso calc R 1 . .
C C11 0.04377(7) 0.56410(12) 0.21963(12) 0.0358(2) Uani d . 1 . .
C C12 0.04428(8) 0.66074(13) 0.10355(13) 0.0403(3) Uani d . 1 . .
H H12A -0.0055 0.7241 0.0736 0.048 Uiso calc R 1 . .
C C13 0.11769(8) 0.66500(13) 0.03071(13) 0.0399(3) Uani d . 1 . .
H H13A 0.1185 0.7324 -0.0479 0.048 Uiso calc R 1 . .
C C14 0.26552(8) 0.28301(13) 0.34102(13) 0.0411(3) Uani d . 1 . .
H H14A 0.3220 0.2280 0.3534 0.062 Uiso calc R 1 . .
H H14B 0.2124 0.2210 0.3105 0.062 Uiso calc R 1 . .
H H14C 0.2635 0.3288 0.4393 0.062 Uiso calc R 1 . .
C C15 -0.03198(7) 0.55965(13) 0.29606(13) 0.0411(3) Uani d . 1 . .
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
C8 O1 C7 . . 117.61(8) ?
C9 O2 C14 . . 117.38(8) ?
C2 C1 C6 . . 120.51(12) ?
C2 C1 H1A . . 119.7 ?
C6 C1 H1A . . 119.7 ?
C3 C2 C1 . . 120.43(12) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C2 C3 C4 . . 119.72(12) ?
C2 C3 H3A . . 120.1 ?
C4 C3 H3A . . 120.1 ?
C3 C4 C5 . . 120.20(12) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
C6 C5 C4 . . 120.58(11) ?
C6 C5 H5A . . 119.7 ?
C4 C5 H5A . . 119.7 ?
C5 C6 C1 . . 118.55(11) ?
C5 C6 C7 . . 120.06(10) ?
C1 C6 C7 . . 121.28(11) ?
O1 C7 C6 . . 106.16(9) ?
O1 C7 H7A . . 110.5 ?
C6 C7 H7A . . 110.5 ?
O1 C7 H7B . . 110.5 ?
C6 C7 H7B . . 110.5 ?
H7A C7 H7B . . 108.7 ?
O1 C8 C13 . . 125.25(10) ?
O1 C8 C9 . . 115.10(9) ?
C13 C8 C9 . . 119.65(9) ?
O2 C9 C10 . . 125.03(9) ?
O2 C9 C8 . . 115.01(9) ?
C10 C9 C8 . . 119.96(9) ?
C9 C10 C11 . . 119.51(10) ?
C9 C10 H10A . . 120.2 ?
C11 C10 H10A . . 120.2 ?
C12 C11 C10 . . 120.68(10) ?
C12 C11 C15 . . 120.10(10) ?
C10 C11 C15 . . 119.22(10) ?
C11 C12 C13 . . 119.87(10) ?
C11 C12 H12A . . 120.1 ?
C13 C12 H12A . . 120.1 ?
C8 C13 C12 . . 120.33(10) ?
C8 C13 H13A . . 119.8 ?
C12 C13 H13A . . 119.8 ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N1 C15 C11 . . 178.73(13) ?
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
C1 C2 . 1.3872(18) ?
C1 C6 . 1.3916(17) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.3673(19) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.3810(18) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.3878(17) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3834(16) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.4967(15) ?
C7 O1 . 1.4478(13) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 O1 . 1.3535(12) ?
C8 C13 . 1.3870(15) ?
C8 C9 . 1.4161(15) ?
C9 O2 . 1.3624(12) ?
C9 C10 . 1.3794(14) ?
C10 C11 . 1.4046(14) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.3822(16) ?
C11 C15 . 1.4411(14) ?
C12 C13 . 1.3897(15) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C14 O2 . 1.4244(13) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 N1 . 1.1402(15) ?
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
C14 H14B N1 2_545 0.98 2.58 3.5170(17) 160
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 694245
