#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/33/2223351.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_2223351
loop_
_publ_author_name
'Gao, Jin-Sheng'
'Liu, Ying'
'Zhang, Shuang'
'Zuo, Dian-Fa'
'Hou, Guang-Feng'
_publ_section_title
;
 1,4-Bis(pyridin-3-ylmethoxy)benzene
;
_journal_coeditor_code           CV2613
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2457
_journal_paper_doi               10.1107/S1600536809036265
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H16 N2 O2'
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_systematic
;
1,4-Bis(pyridin-3-ylmethoxy)benzene
;
_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                 90.60(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.852(5)
_cell_length_b                   5.688(3)
_cell_length_c                   18.861(12)
_cell_measurement_reflns_used    4889
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.66
_cell_volume                     735.1(8)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6855
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0408
_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+0.0635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                1213
_reflns_number_total             1684
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2613.cif
_cod_data_source_block           I
_cod_original_cell_volume        735.0(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223351
_cod_database_fobs_code          2223351
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
C C1 0.8460(2) -0.0288(3) 0.20865(8) 0.0485(4) Uani d . 1 . .
H H1 0.9650 -0.0611 0.2307 0.058 Uiso calc R 1 . .
C C2 0.7721(2) -0.1906(3) 0.16191(8) 0.0530(4) Uani d . 1 . .
H H2 0.8404 -0.3281 0.1524 0.064 Uiso calc R 1 . .
C C3 0.5951(2) -0.1469(3) 0.12921(8) 0.0484(4) Uani d . 1 . .
H H3 0.5422 -0.2545 0.0972 0.058 Uiso calc R 1 . .
C C4 0.49744(18) 0.0588(2) 0.14460(7) 0.0367(3) Uani d . 1 . .
C C5 0.5857(2) 0.2119(3) 0.19208(7) 0.0428(4) Uani d . 1 . .
H H5 0.5213 0.3517 0.2022 0.051 Uiso calc R 1 . .
C C6 0.30072(19) 0.1158(3) 0.11378(7) 0.0433(4) Uani d . 1 . .
H H6A 0.2437 -0.0233 0.0922 0.052 Uiso calc R 1 . .
H H6B 0.2144 0.1704 0.1507 0.052 Uiso calc R 1 . .
C C7 0.15874(17) 0.3913(2) 0.03246(7) 0.0368(3) Uani d . 1 . .
C C8 -0.02824(18) 0.3034(3) 0.04198(7) 0.0408(3) Uani d . 1 . .
H H8 -0.0477 0.1710 0.0700 0.049 Uiso calc R 1 . .
C C9 -0.18583(18) 0.4142(3) 0.00955(7) 0.0408(3) Uani d . 1 . .
H H9 -0.3112 0.3563 0.0163 0.049 Uiso calc R 1 . .
N N1 0.75686(17) 0.1729(2) 0.22431(7) 0.0510(4) Uani d . 1 . .
O O1 0.32526(13) 0.29466(19) 0.06180(5) 0.0509(3) Uani d . 1 . .
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
C1 0.0308(7) 0.0572(9) 0.0571(9) 0.0002(6) -0.0101(6) 0.0171(7)
C2 0.0439(9) 0.0449(8) 0.0700(10) 0.0117(7) -0.0063(7) 0.0064(8)
C3 0.0487(8) 0.0432(8) 0.0532(8) 0.0035(7) -0.0108(6) -0.0038(7)
C4 0.0308(6) 0.0395(7) 0.0396(7) -0.0005(5) -0.0056(5) 0.0083(6)
C5 0.0371(7) 0.0388(7) 0.0525(8) 0.0016(6) -0.0069(6) 0.0008(6)
C6 0.0334(7) 0.0482(8) 0.0482(8) -0.0010(6) -0.0093(6) 0.0109(6)
C7 0.0264(6) 0.0465(8) 0.0374(6) 0.0056(5) -0.0046(5) 0.0038(6)
C8 0.0308(7) 0.0475(8) 0.0438(7) -0.0007(6) -0.0045(5) 0.0111(6)
C9 0.0250(6) 0.0530(8) 0.0444(7) -0.0016(6) -0.0030(5) 0.0073(6)
N1 0.0394(7) 0.0538(8) 0.0596(8) -0.0056(6) -0.0145(6) 0.0004(6)
O1 0.0269(5) 0.0683(7) 0.0573(6) 0.0058(4) -0.0048(4) 0.0267(5)
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 C2 . . 123.64(13) ?
N1 C1 H1 . . 118.2 ?
C2 C1 H1 . . 118.2 ?
C1 C2 C3 . . 119.03(14) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C2 C3 C4 . . 119.04(14) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C3 C4 C5 . . 117.37(13) ?
C3 C4 C6 . . 122.56(13) ?
C5 C4 C6 . . 120.04(13) ?
N1 C5 C4 . . 124.50(14) ?
N1 C5 H5 . . 117.7 ?
C4 C5 H5 . . 117.7 ?
O1 C6 C4 . . 108.04(11) ?
O1 C6 H6A . . 110.1 ?
C4 C6 H6A . . 110.1 ?
O1 C6 H6B . . 110.1 ?
C4 C6 H6B . . 110.1 ?
H6A C6 H6B . . 108.4 ?
C9 C7 O1 3_565 . 115.88(11) ?
C9 C7 C8 3_565 . 119.64(12) ?
O1 C7 C8 . . 124.47(13) ?
C9 C8 C7 . . 119.64(14) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C7 C9 C8 3_565 . 120.71(12) ?
C7 C9 H9 3_565 . 119.6 ?
C8 C9 H9 . . 119.6 ?
C5 N1 C1 . . 116.41(13) ?
C7 O1 C6 . . 117.28(10) ?
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 N1 . 1.334(2) ?
C1 C2 . 1.368(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.378(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.380(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.3839(19) ?
C4 C6 . 1.4979(19) ?
C5 N1 . 1.3336(19) ?
C5 H5 . 0.9300 ?
C6 O1 . 1.4239(17) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C9 3_565 1.374(2) ?
C7 O1 . 1.3773(17) ?
C7 C8 . 1.389(2) ?
C8 C9 . 1.3869(19) ?
C8 H8 . 0.9300 ?
C9 C7 3_565 1.374(2) ?
C9 H9 . 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
C1 H1 N1 2_745 0.93 2.57 3.437(3) 155.2
