#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/21/2222105.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_2222105
loop_
_publ_author_name
'Zhao, Min Min'
'Li, Yong Hua'
'Wu, De Hong'
'Wan, Qing'
_publ_section_title
;
 4-(6-Quinolyloxymethyl)benzonitrile
;
_journal_coeditor_code           LX2099
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1261
_journal_paper_doi               10.1107/S1600536809016560
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H12 N2 O'
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_chemical_name_systematic
;
4-(6-Quinolyloxymethyl)benzonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.81(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.466(2)
_cell_length_b                   13.078(3)
_cell_length_c                   10.857(2)
_cell_measurement_reflns_used    10916
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.54
_cell_measurement_theta_min      6.23
_cell_volume                     1343.9(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω
_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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12007
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.127
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0493
_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)+(0.0500P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                1956
_reflns_number_total             2622
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2099.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222105
_cod_database_fobs_code          2222105
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_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 0.48772(13) 0.46617(8) 0.29375(10) 0.0598(4) Uani d . 1 . .
N N1 0.40388(17) 0.05815(11) 0.18437(15) 0.0620(4) Uani d . 1 . .
N N2 0.7214(2) 0.99565(14) 0.44097(18) 0.0841(6) Uani d . 1 . .
C C1 0.46122(17) 0.36816(12) 0.25614(16) 0.0484(4) Uani d . 1 . .
C C2 0.49253(18) 0.29346(13) 0.34606(16) 0.0538(5) Uani d . 1 . .
H H2 0.5251 0.3134 0.4236 0.065 Uiso calc R 1 . .
C C3 0.47550(19) 0.19262(13) 0.32018(16) 0.0547(5) Uani d . 1 . .
H H3 0.4984 0.1441 0.3798 0.066 Uiso calc R 1 . .
C C4 0.42364(17) 0.16054(12) 0.20416(16) 0.0478(4) Uani d . 1 . .
C C5 0.3504(2) 0.03171(15) 0.07708(19) 0.0701(6) Uani d . 1 . .
H H5 0.3356 -0.0376 0.0624 0.084 Uiso calc R 1 . .
C C6 0.3139(2) 0.10024(15) -0.01687(19) 0.0691(6) Uani d . 1 . .
H H6 0.2764 0.0765 -0.0912 0.083 Uiso calc R 1 . .
C C7 0.33370(19) 0.20151(13) 0.00168(16) 0.0570(5) Uani d . 1 . .
H H7 0.3103 0.2482 -0.0599 0.068 Uiso calc R 1 . .
C C8 0.39011(16) 0.23550(12) 0.11523(15) 0.0451(4) Uani d . 1 . .
C C9 0.40997(17) 0.34014(12) 0.14319(15) 0.0474(4) Uani d . 1 . .
H H9 0.3881 0.3898 0.0846 0.057 Uiso calc R 1 . .
C C10 0.45964(19) 0.54615(12) 0.20742(16) 0.0526(4) Uani d . 1 . .
H H10A 0.3588 0.5517 0.1918 0.063 Uiso calc R 1 . .
H H10B 0.5056 0.5316 0.1301 0.063 Uiso calc R 1 . .
C C11 0.51542(17) 0.64433(12) 0.26109(15) 0.0478(4) Uani d . 1 . .
C C12 0.43628(18) 0.73295(12) 0.25445(17) 0.0531(5) Uani d . 1 . .
H H12 0.3466 0.7310 0.2185 0.064 Uiso calc R 1 . .
C C13 0.48752(18) 0.82412(13) 0.30002(17) 0.0552(5) Uani d . 1 . .
H H13 0.4330 0.8831 0.2948 0.066 Uiso calc R 1 . .
C C14 0.62108(18) 0.82714(12) 0.35366(15) 0.0494(4) Uani d . 1 . .
C C15 0.70261(19) 0.73897(13) 0.35993(17) 0.0576(5) Uani d . 1 . .
H H15 0.7927 0.7410 0.3951 0.069 Uiso calc R 1 . .
C C16 0.64942(19) 0.64883(13) 0.31393(17) 0.0574(5) Uani d . 1 . .
H H16 0.7042 0.5899 0.3183 0.069 Uiso calc R 1 . .
C C17 0.6764(2) 0.92132(15) 0.40205(17) 0.0607(5) 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
C1 O1 C10 . . 117.34(12) ?
C5 N1 C4 . . 116.62(16) ?
C9 C1 O1 . . 125.61(15) ?
C9 C1 C2 . . 120.38(15) ?
O1 C1 C2 . . 114.01(14) ?
C3 C2 C1 . . 120.44(16) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 120.86(16) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
N1 C4 C8 . . 122.97(16) ?
N1 C4 C3 . . 118.47(15) ?
C8 C4 C3 . . 118.53(15) ?
N1 C5 C6 . . 124.62(18) ?
N1 C5 H5 . . 117.7 ?
C6 C5 H5 . . 117.7 ?
C7 C6 C5 . . 119.14(18) ?
C7 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
C6 C7 C8 . . 119.31(17) ?
C6 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
C7 C8 C4 . . 117.33(15) ?
C7 C8 C9 . . 122.75(15) ?
C4 C8 C9 . . 119.89(15) ?
C1 C9 C8 . . 119.88(15) ?
C1 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
O1 C10 C11 . . 108.09(13) ?
O1 C10 H10A . . 110.1 ?
C11 C10 H10A . . 110.1 ?
O1 C10 H10B . . 110.1 ?
C11 C10 H10B . . 110.1 ?
H10A C10 H10B . . 108.4 ?
C12 C11 C16 . . 118.59(15) ?
C12 C11 C10 . . 120.62(15) ?
C16 C11 C10 . . 120.74(15) ?
C13 C12 C11 . . 121.32(16) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C12 C13 C14 . . 119.39(16) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C13 C14 C15 . . 120.02(15) ?
C13 C14 C17 . . 120.32(16) ?
C15 C14 C17 . . 119.67(16) ?
C16 C15 C14 . . 119.63(16) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C15 C16 C11 . . 121.04(16) ?
C15 C16 H16 . . 119.5 ?
C11 C16 H16 . . 119.5 ?
N2 C17 C14 . . 179.4(2) ?
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
O1 C1 . 1.3674(19) ?
O1 C10 . 1.4269(19) ?
N1 C5 . 1.310(2) ?
N1 C4 . 1.369(2) ?
N2 C17 . 1.140(2) ?
C1 C9 . 1.363(2) ?
C1 C2 . 1.410(2) ?
C2 C3 . 1.358(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.409(2) ?
C3 H3 . 0.9300 ?
C4 C8 . 1.409(2) ?
C5 C6 . 1.398(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.352(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.408(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.414(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.503(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.381(2) ?
C11 C16 . 1.386(2) ?
C12 C13 . 1.377(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.385(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.389(2) ?
C14 C17 . 1.435(2) ?
C15 C16 . 1.373(2) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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
C12 H12 Cg 2_555 0.93 2.83 3.613(2) 142.4
C13 H13 N1 1_565 0.93 2.60 3.398(2) 144.6
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
C10 O1 C1 C9 . . . . -0.1(2) ?
C10 O1 C1 C2 . . . . 179.55(14) ?
C9 C1 C2 C3 . . . . 1.7(3) ?
O1 C1 C2 C3 . . . . -177.98(16) ?
C1 C2 C3 C4 . . . . -1.3(3) ?
C5 N1 C4 C8 . . . . -0.4(3) ?
C5 N1 C4 C3 . . . . 177.42(17) ?
C2 C3 C4 N1 . . . . -177.77(16) ?
C2 C3 C4 C8 . . . . 0.2(3) ?
C4 N1 C5 C6 . . . . 0.5(3) ?
N1 C5 C6 C7 . . . . -0.1(3) ?
C5 C6 C7 C8 . . . . -0.2(3) ?
C6 C7 C8 C4 . . . . 0.3(2) ?
C6 C7 C8 C9 . . . . -178.00(17) ?
N1 C4 C8 C7 . . . . 0.1(2) ?
C3 C4 C8 C7 . . . . -177.76(16) ?
N1 C4 C8 C9 . . . . 178.39(15) ?
C3 C4 C8 C9 . . . . 0.5(2) ?
O1 C1 C9 C8 . . . . 178.66(15) ?
C2 C1 C9 C8 . . . . -1.0(2) ?
C7 C8 C9 C1 . . . . 178.09(16) ?
C4 C8 C9 C1 . . . . -0.1(2) ?
C1 O1 C10 C11 . . . . -171.97(14) ?
O1 C10 C11 C12 . . . . -135.85(16) ?
O1 C10 C11 C16 . . . . 46.7(2) ?
C16 C11 C12 C13 . . . . -0.6(3) ?
C10 C11 C12 C13 . . . . -178.12(16) ?
C11 C12 C13 C14 . . . . 0.0(3) ?
C12 C13 C14 C15 . . . . 0.7(3) ?
C12 C13 C14 C17 . . . . -179.84(16) ?
C13 C14 C15 C16 . . . . -0.7(3) ?
C17 C14 C15 C16 . . . . 179.81(17) ?
C14 C15 C16 C11 . . . . 0.1(3) ?
C12 C11 C16 C15 . . . . 0.6(3) ?
C10 C11 C16 C15 . . . . 178.10(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742315
