#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/86/2208673.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_2208673
loop_
_publ_author_name
'Zheng-Bo Chen'
'Jun Wu'
'Pei-Zhi Zhang'
'Pei-Min Zhang'
_publ_section_title
;
 Ethyl 4-(2-chloro-4-nitrophenoxy)benzoate
;
_journal_coeditor_code           LH6590
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1336
_journal_page_last               o1337
_journal_paper_doi               10.1107/S160053680600804X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H12 Cl N O5'
_chemical_formula_moiety         'C15 H12 Cl N O5'
_chemical_formula_sum            'C15 H12 Cl N O5'
_chemical_formula_weight         321.71
_chemical_name_systematic
;
Ethyl 4-(2-chloro-4-nitrophenoxy)benzoate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.230(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.890(6)
_cell_length_b                   8.846(3)
_cell_length_c                   13.967(5)
_cell_measurement_reflns_used    10694
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1484.5(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    SHELXL97
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14122
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664.00
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0440
_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)+(0.066P)²+0.1257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                2406
_reflns_number_total             3398
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6590.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2208673
_cod_database_fobs_code          2208673
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
Cl Cl1 0.72198(6) 0.66363(6) 0.97648(4) 0.0967(3) Uani d . 1
O O5 0.41489(11) 0.18920(16) 0.39209(9) 0.0727(4) Uani d . 1
O O3 0.53429(12) 0.54450(13) 0.80786(8) 0.0732(4) Uani d . 1
O O4 0.25972(11) 0.32380(17) 0.35358(10) 0.0813(4) Uani d . 1
O O2 0.63498(12) 0.04814(16) 1.14720(10) 0.0795(4) Uani d . 1
O O1 0.74092(12) 0.22583(18) 1.23393(9) 0.0846(4) Uani d . 1
C C10 0.40244(12) 0.35672(17) 0.51675(11) 0.0480(4) Uani d . 1
N N1 0.67267(13) 0.17610(18) 1.15490(10) 0.0611(4) Uani d . 1
C C1 0.63443(13) 0.27425(18) 1.06446(11) 0.0514(4) Uani d . 1
C C2 0.54635(14) 0.22717(19) 0.97931(12) 0.0569(4) Uani d . 1
H H2 0.5107 0.1361 0.9801 0.068 Uiso calc R 1
C C13 0.35030(13) 0.29030(19) 0.41274(12) 0.0526(4) Uani d . 1
C C11 0.34665(13) 0.46917(17) 0.54669(12) 0.0542(4) Uani d . 1
H H11 0.2788 0.5039 0.5007 0.065 Uiso calc R 1
C C9 0.50434(13) 0.3070(2) 0.58487(12) 0.0583(4) Uani d . 1
H H9 0.5433 0.2326 0.5649 0.070 Uiso calc R 1
C C5 0.65416(14) 0.49633(19) 0.97837(12) 0.0569(4) Uani d . 1
C C4 0.56627(14) 0.45067(17) 0.89119(11) 0.0545(4) Uani d . 1
C C12 0.38990(14) 0.53095(18) 0.64376(12) 0.0589(4) Uani d . 1
H H12 0.3520 0.6069 0.6636 0.071 Uiso calc R 1
C C7 0.49012(14) 0.47804(18) 0.71052(11) 0.0563(4) Uani d . 1
C C6 0.68845(14) 0.40878(19) 1.06586(12) 0.0578(4) Uani d . 1
H H6 0.7467 0.4399 1.1245 0.069 Uiso calc R 1
C C8 0.54819(15) 0.3677(2) 0.68232(13) 0.0644(5) Uani d . 1
H H8 0.6164 0.3341 0.7284 0.077 Uiso calc R 1
C C3 0.51213(14) 0.31683(18) 0.89322(13) 0.0594(4) Uani d . 1
H H3 0.4519 0.2871 0.8358 0.071 Uiso calc R 1
C C14 0.37253(19) 0.1138(3) 0.29342(15) 0.0841(6) Uani d . 1
H H14A 0.3291 0.1840 0.2408 0.101 Uiso calc R 1
H H14B 0.3248 0.0303 0.2959 0.101 Uiso calc R 1
C C15 0.4673(2) 0.0580(3) 0.2695(2) 0.0959(7) Uani d . 1
H H15A 0.5112 0.1419 0.2626 0.144 Uiso calc R 1
H H15B 0.4406 0.0021 0.2063 0.144 Uiso calc R 1
H H15C 0.5121 -0.0067 0.3239 0.144 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.0000 '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
C13 O5 C14 117.94(14) y
C4 O3 C7 117.63(12) y
C11 C10 C9 119.32(15) ?
C11 C10 C13 118.82(13) ?
C9 C10 C13 121.85(15) ?
O1 N1 O2 123.27(16) y
O1 N1 C1 118.36(16) ?
O2 N1 C1 118.37(14) ?
C6 C1 C2 121.90(15) ?
C6 C1 N1 119.38(13) ?
C2 C1 N1 118.71(15) ?
C3 C2 C1 118.96(15) ?
C3 C2 H2 120.5 ?
C1 C2 H2 120.5 ?
O4 C13 O5 123.36(16) y
O4 C13 C10 124.08(16) ?
O5 C13 C10 112.56(13) ?
C10 C11 C12 121.00(14) ?
C10 C11 H11 119.5 ?
C12 C11 H11 119.5 ?
C8 C9 C10 120.15(17) ?
C8 C9 H9 119.9 ?
C10 C9 H9 119.9 ?
C6 C5 C4 120.79(15) ?
C6 C5 Cl1 119.65(12) ?
C4 C5 Cl1 119.56(13) ?
O3 C4 C3 122.69(13) ?
O3 C4 C5 117.95(14) ?
C3 C4 C5 119.30(15) ?
C7 C12 C11 118.61(16) ?
C7 C12 H12 120.7 ?
C11 C12 H12 120.7 ?
C8 C7 C12 121.64(15) ?
C8 C7 O3 120.37(15) ?
C12 C7 O3 117.93(16) ?
C1 C6 C5 118.41(14) ?
C1 C6 H6 120.8 ?
C5 C6 H6 120.8 ?
C7 C8 C9 119.27(15) ?
C7 C8 H8 120.4 ?
C9 C8 H8 120.4 ?
C2 C3 C4 120.61(14) ?
C2 C3 H3 119.7 ?
C4 C3 H3 119.7 ?
O5 C14 C15 108.32(18) ?
O5 C14 H14A 110.0 ?
C15 C14 H14A 110.0 ?
O5 C14 H14B 110.0 ?
C15 C14 H14B 110.0 ?
H14A C14 H14B 108.4 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.7239(18)
O5 C13 1.323(2)
O5 C14 1.448(2)
O3 C4 1.3661(19)
O3 C7 1.3991(18)
O4 C13 1.1980(19)
O2 N1 1.221(2)
O1 N1 1.2176(18)
C10 C11 1.378(2)
C10 C9 1.385(2)
C10 C13 1.483(2)
N1 C1 1.463(2)
C1 C6 1.375(2)
C1 C2 1.378(2)
C2 C3 1.373(2)
C2 H2 0.9300
C11 C12 1.378(2)
C11 H11 0.9300
C9 C8 1.379(2)
C9 H9 0.9300
C5 C6 1.377(2)
C5 C4 1.389(2)
C4 C3 1.380(2)
C12 C7 1.373(2)
C12 H12 0.9300
C7 C8 1.372(3)
C6 H6 0.9300
C8 H8 0.9300
C3 H3 0.9300
C14 C15 1.464(3)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
_geom_hbond_publ_flag
C3 H3 O1 4_454 0.93 2.58 3.418(3) 151 y
C8 H8 O4 4_555 0.93 2.47 3.362(3) 162 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7401899
