#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/34/2223423.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_2223423
loop_
_publ_author_name
'Yu, Hui-ling'
_publ_section_title
;
 2-Chloro-1-(3-fluorobenzyloxy)-4-nitrobenzene
;
_journal_coeditor_code           HK2758
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2327
_journal_paper_doi               10.1107/S160053680903431X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H9 Cl F N O3'
_chemical_formula_moiety         'C13 H9 Cl F N O3'
_chemical_formula_sum            'C13 H9 Cl F N O3'
_chemical_formula_weight         281.66
_chemical_name_common            2-Chloro-1-(3-fluorobenzyloxy)-4-nitrobenzen
_chemical_name_systematic
;
2-Chloro-1-(3-fluorobenzyloxy)-4-nitrobenzene
;
_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                 96.94(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3290(17)
_cell_length_b                   12.640(3)
_cell_length_c                   11.875(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1241.0(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2411
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.9684
_exptl_absorpt_correction_T_min  0.9094
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0519
_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)+(0.07P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                1340
_reflns_number_total             2248
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2758.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223423
_cod_database_fobs_code          2223423
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
Cl Cl 0.81771(13) 0.51262(7) 0.07511(8) 0.0802(4) Uani d . 1 . .
F F 0.4335(3) 1.00189(17) -0.29984(19) 0.0996(8) Uani d . 1 . .
O O1 0.6878(3) 0.72025(15) 0.07000(17) 0.0582(6) Uani d . 1 . .
O O2 1.1588(3) 0.5447(2) 0.4720(2) 0.0846(8) Uani d . 1 . .
O O3 1.0836(4) 0.6867(3) 0.5501(2) 0.1058(10) Uani d . 1 . .
N N 1.0804(3) 0.6268(3) 0.4700(3) 0.0694(8) Uani d . 1 . .
C C1 0.3405(4) 0.8293(3) -0.2781(3) 0.0670(10) Uani d . 1 . .
H H1A 0.2801 0.8325 -0.3492 0.080 Uiso calc R 1 . .
C C2 0.4320(4) 0.9129(3) -0.2358(3) 0.0629(9) Uani d . 1 . .
C C3 0.5233(4) 0.9117(2) -0.1320(3) 0.0550(8) Uani d . 1 . .
H H3A 0.5858 0.9700 -0.1069 0.066 Uiso calc R 1 . .
C C4 0.5210(4) 0.8224(2) -0.0653(3) 0.0513(8) Uani d . 1 . .
C C5 0.4296(4) 0.7364(3) -0.1061(3) 0.0630(9) Uani d . 1 . .
H H5A 0.4279 0.6756 -0.0621 0.076 Uiso calc R 1 . .
C C6 0.3407(4) 0.7401(3) -0.2118(3) 0.0707(10) Uani d . 1 . .
H H6A 0.2801 0.6815 -0.2386 0.085 Uiso calc R 1 . .
C C7 0.6137(4) 0.8219(2) 0.0507(3) 0.0587(9) Uani d . 1 . .
H H7A 0.6959 0.8767 0.0564 0.070 Uiso calc R 1 . .
H H7B 0.5415 0.8358 0.1073 0.070 Uiso calc R 1 . .
C C8 0.7811(4) 0.7033(2) 0.1694(3) 0.0492(8) Uani d . 1 . .
C C9 0.8086(4) 0.7766(2) 0.2567(3) 0.0564(8) Uani d . 1 . .
H H9A 0.7609 0.8431 0.2488 0.068 Uiso calc R 1 . .
C C10 0.9064(4) 0.7510(3) 0.3551(3) 0.0597(9) Uani d . 1 . .
H H10A 0.9250 0.8002 0.4135 0.072 Uiso calc R 1 . .
C C11 0.9755(4) 0.6531(2) 0.3662(3) 0.0531(8) Uani d . 1 . .
C C12 0.9495(4) 0.5787(3) 0.2808(3) 0.0575(8) Uani d . 1 . .
H H12A 0.9970 0.5122 0.2896 0.069 Uiso calc R 1 . .
C C13 0.8532(4) 0.6039(2) 0.1836(3) 0.0530(8) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 . . 118.3(2) ?
O2 N C11 . . 118.2(3) ?
O3 N O2 . . 123.5(3) ?
O3 N C11 . . 118.3(3) ?
C2 C1 C6 . . 117.6(3) ?
C2 C1 H1A . . 121.2 ?
C6 C1 H1A . . 121.2 ?
F C2 C1 . . 118.5(3) ?
F C2 C3 . . 118.1(3) ?
C1 C2 C3 . . 123.3(3) ?
C2 C3 C4 . . 118.7(3) ?
C2 C3 H3A . . 120.6 ?
C4 C3 H3A . . 120.6 ?
C3 C4 C5 . . 119.2(3) ?
C3 C4 C7 . . 119.4(3) ?
C5 C4 C7 . . 121.4(3) ?
C6 C5 C4 . . 120.3(3) ?
C6 C5 H5A . . 119.8 ?
C4 C5 H5A . . 119.8 ?
C1 C6 C5 . . 120.8(3) ?
C1 C6 H6A . . 119.6 ?
C5 C6 H6A . . 119.6 ?
O1 C7 C4 . . 108.4(2) ?
O1 C7 H7A . . 110.0 ?
C4 C7 H7A . . 110.0 ?
O1 C7 H7B . . 110.0 ?
C4 C7 H7B . . 110.0 ?
H7A C7 H7B . . 108.4 ?
O1 C8 C9 . . 124.9(3) ?
O1 C8 C13 . . 116.3(3) ?
C9 C8 C13 . . 118.8(3) ?
C10 C9 C8 . . 120.3(3) ?
C10 C9 H9A . . 119.9 ?
C8 C9 H9A . . 119.9 ?
C11 C10 C9 . . 119.5(3) ?
C11 C10 H10A . . 120.3 ?
C9 C10 H10A . . 120.3 ?
C10 C11 C12 . . 121.3(3) ?
C10 C11 N . . 119.3(3) ?
C12 C11 N . . 119.4(3) ?
C13 C12 C11 . . 119.2(3) ?
C13 C12 H12A . . 120.4 ?
C11 C12 H12A . . 120.4 ?
C12 C13 C8 . . 120.9(3) ?
C12 C13 Cl . . 120.4(3) ?
C8 C13 Cl . . 118.6(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
Cl C13 . 1.728(3) ?
F C2 . 1.359(4) ?
O1 C7 . 1.432(3) ?
O1 C8 . 1.350(4) ?
N O2 . 1.225(4) ?
N O3 . 1.214(4) ?
N C11 . 1.460(4) ?
C1 C2 . 1.363(5) ?
C1 C6 . 1.375(4) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.367(4) ?
C3 C4 . 1.381(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.382(4) ?
C4 C7 . 1.496(4) ?
C5 C6 . 1.379(5) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.388(4) ?
C8 C13 . 1.394(4) ?
C9 C10 . 1.380(5) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.366(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.380(4) ?
C12 C13 . 1.361(4) ?
C12 H12A . 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
C7 H7A O2 2_755 0.97 2.49 3.423(4) 162
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
C6 C1 C2 F . . . . -180.0(3) ?
C6 C1 C2 C3 . . . . 0.3(5) ?
F C2 C3 C4 . . . . 179.1(3) ?
C1 C2 C3 C4 . . . . -1.2(5) ?
C2 C3 C4 C5 . . . . 1.3(5) ?
C2 C3 C4 C7 . . . . -177.0(3) ?
C3 C4 C5 C6 . . . . -0.5(5) ?
C7 C4 C5 C6 . . . . 177.7(3) ?
C2 C1 C6 C5 . . . . 0.5(5) ?
C4 C5 C6 C1 . . . . -0.4(5) ?
C8 O1 C7 C4 . . . . 178.5(2) ?
C3 C4 C7 O1 . . . . -140.2(3) ?
C5 C4 C7 O1 . . . . 41.6(4) ?
C7 O1 C8 C9 . . . . 1.5(4) ?
C7 O1 C8 C13 . . . . -178.8(3) ?
O1 C8 C9 C10 . . . . -180.0(3) ?
C13 C8 C9 C10 . . . . 0.3(5) ?
C8 C9 C10 C11 . . . . -0.2(5) ?
C9 C10 C11 C12 . . . . -0.1(5) ?
C9 C10 C11 N . . . . 179.3(3) ?
O3 N C11 C10 . . . . 11.0(5) ?
O2 N C11 C10 . . . . -170.0(3) ?
O3 N C11 C12 . . . . -169.6(3) ?
O2 N C11 C12 . . . . 9.5(4) ?
C10 C11 C12 C13 . . . . 0.2(5) ?
N C11 C12 C13 . . . . -179.2(3) ?
C11 C12 C13 C8 . . . . -0.1(4) ?
C11 C12 C13 Cl . . . . -179.9(2) ?
O1 C8 C13 C12 . . . . -179.9(3) ?
C9 C8 C13 C12 . . . . -0.2(4) ?
O1 C8 C13 Cl . . . . -0.1(4) ?
C9 C8 C13 Cl . . . . 179.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5415497
