#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/46/2204688.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_2204688
loop_
_publ_author_name
'Vencato, Ivo'
'Ferri, Pedro H.'
'Santos, Suzana C.'
'Santos, Lourivaldo S.'
'Lariucci, Carlito'
'Napolitano, Hamilton B.'
_publ_section_title
;
 1-(4-Methoxyphenyl)-2-(2-nitrophenoxy)propan-1-one
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2498
_journal_page_last               o2500
_journal_paper_doi               10.1107/S1600536804030260
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H15 N O5'
_chemical_formula_moiety         'C16 H15 N O5'
_chemical_formula_sum            'C16 H15 N O5'
_chemical_formula_weight         301.29
_chemical_melting_point          .403E-305
_chemical_name_systematic
;
1-(4-Methoxyphenyl)-2-(2-nitrophenoxy)propan-1-one
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.99(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.851(2)
_cell_length_b                   9.858(2)
_cell_length_c                   17.255(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.61
_cell_measurement_theta_min      10.37
_cell_volume                     1499.8(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       κ-geometry
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled 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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2738
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.201
_refine_ls_extinction_coef       0.056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0651P)²+0.3965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.118
_refine_ls_wR_factor_ref         0.129
_reflns_number_gt                2080
_reflns_number_total             2643
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gh6006.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P  1 21/c 1'
_cod_database_code               2204688
_cod_database_fobs_code          2204688
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_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_type_symbol
O1 0.14241(14) 0.93771(13) 0.17171(7) 0.0576(4) Uani d . 1 O
O2 0.10978(15) 0.76576(13) 0.29073(8) 0.0607(4) Uani d . 1 O
O4 0.2464(2) 0.9577(2) 0.02752(10) 0.1005(6) Uani d . 1 O
O5 0.4702(2) 0.87703(19) 0.05173(11) 0.1018(6) Uani d . 1 O
N1 0.3620(2) 0.94670(19) 0.06865(11) 0.0674(5) Uani d . 1 N
C1 0.3798(2) 1.02035(18) 0.14230(10) 0.0514(5) Uani d . 1 C
C2 0.5114(2) 1.0928(2) 0.15909(13) 0.0660(6) Uani d . 1 C
H2 0.5854 1.0945 0.1240 0.079 Uiso calc R 1 H
C3 0.5330(2) 1.1630(3) 0.22829(14) 0.0720(6) Uani d . 1 C
H3 0.624(3) 1.212(2) 0.2395(14) 0.086 Uiso d . 1 H
C4 0.4232(2) 1.1562(2) 0.28001(13) 0.0661(6) Uani d . 1 C
H4 0.4377 1.2025 0.3270 0.079 Uiso calc R 1 H
C5 0.2924(2) 1.0823(2) 0.26354(11) 0.0552(5) Uani d . 1 C
H5 0.2207 1.0781 0.2998 0.066 Uiso calc R 1 H
C6 0.26663(19) 1.01402(17) 0.19345(10) 0.0463(4) Uani d . 1 C
C7 0.0126(2) 0.95223(19) 0.21514(10) 0.0491(4) Uani d . 1 C
H7 0.000(2) 1.045(2) 0.2281(12) 0.059 Uiso d . 1 H
C8 0.02786(18) 0.86543(17) 0.28873(10) 0.0455(4) Uani d . 1 C
C9 -0.06337(18) 0.89992(17) 0.35361(10) 0.0450(4) Uani d . 1 C
C10 -0.1288(2) 1.02644(18) 0.36237(11) 0.0532(5) Uani d . 1 C
H10 -0.1199 1.0924 0.3245 0.064 Uiso calc R 1 H
C11 -0.2069(2) 1.05634(19) 0.42622(11) 0.0564(5) Uani d . 1 C
H11 -0.2477 1.1424 0.4316 0.068 Uiso calc R 1 H
C12 -0.2245(2) 0.95849(19) 0.48197(10) 0.0520(5) Uani d . 1 C
C13 -0.1634(2) 0.8298(2) 0.47267(11) 0.0618(5) Uani d . 1 C
H13 -0.1773 0.7624 0.5091 0.074 Uiso calc R 1 H
C14 -0.0834(2) 0.80189(19) 0.41038(11) 0.0558(5) Uani d . 1 C
H14 -0.0414 0.7161 0.4056 0.067 Uiso calc R 1 H
C15 -0.3619(3) 1.1076(2) 0.55923(12) 0.0709(6) Uani d . 1 C
H15A -0.4106 1.1069 0.6068 0.106 Uiso calc R 1 H
H15B -0.4351 1.1291 0.5166 0.106 Uiso calc R 1 H
H15C -0.2828 1.1745 0.5625 0.106 Uiso calc R 1 H
C16 -0.1215(2) 0.9033(3) 0.16219(12) 0.0703(6) Uani d . 1 C
H16A -0.1314 0.9579 0.1160 0.105 Uiso calc R 1 H
H16B -0.2122 0.9107 0.1887 0.105 Uiso calc R 1 H
H16C -0.1061 0.8103 0.1484 0.105 Uiso calc R 1 H
O3 -0.29809(17) 0.97659(15) 0.54685(8) 0.0679(4) Uani d . 1 O
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
_geom_angle_publ_flag
C6 O1 C7 117.85(13) yes
O4 N1 O5 123.4(2) yes
O4 N1 C1 119.49(19) yes
O5 N1 C1 117.1(2) yes
C2 C1 C6 122.16(18) ?
C2 C1 N1 117.83(17) ?
C6 C1 N1 120.00(17) ?
C1 C2 C3 119.60(19) ?
C1 C2 H2 120.2 ?
C3 C2 H2 120.2 ?
C4 C3 C2 119.0(2) ?
C4 C3 H3 122.0(14) ?
C2 C3 H3 119.0(14) ?
C5 C4 C3 121.4(2) ?
C5 C4 H4 119.3 ?
C3 C4 H4 119.3 ?
C4 C5 C6 120.60(17) ?
C4 C5 H5 119.7 ?
C6 C5 H5 119.7 ?
O1 C6 C5 125.31(15) ?
O1 C6 C1 117.36(16) ?
C5 C6 C1 117.29(16) ?
O1 C7 C16 105.98(15) ?
O1 C7 C8 111.22(15) yes
C16 C7 C8 109.36(15) ?
O1 C7 H7 109.4(12) ?
C16 C7 H7 110.4(12) ?
C8 C7 H7 110.4(12) ?
O2 C8 C9 121.82(16) yes
O2 C8 C7 118.95(15) yes
C9 C8 C7 119.14(15) yes
C10 C9 C14 117.70(16) ?
C10 C9 C8 123.39(16) ?
C14 C9 C8 118.90(16) ?
C11 C10 C9 121.36(17) ?
C11 C10 H10 119.3 ?
C9 C10 H10 119.3 ?
C12 C11 C10 120.04(17) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
O3 C12 C11 125.09(17) ?
O3 C12 C13 115.72(16) ?
C11 C12 C13 119.18(17) ?
C14 C13 C12 120.44(18) ?
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
C13 C14 C9 121.22(17) ?
C13 C14 H14 119.4 ?
C9 C14 H14 119.4 ?
O3 C15 H15A 109.5 ?
O3 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O3 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C7 C16 H16A 109.5 ?
C7 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C7 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C12 O3 C15 117.77(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 1.358(2) yes
O1 C7 1.432(2) yes
O2 C8 1.220(2) yes
O4 N1 1.198(2) yes
O5 N1 1.234(2) yes
N1 C1 1.460(3) yes
C1 C2 1.376(3) ?
C1 C6 1.393(2) ?
C2 C3 1.379(3) ?
C2 H2 0.9300 ?
C3 C4 1.377(3) ?
C3 H3 0.95(2) ?
C4 C5 1.376(3) ?
C4 H4 0.9300 ?
C5 C6 1.386(3) ?
C5 H5 0.9300 ?
C7 C16 1.513(3) ?
C7 C8 1.527(3) yes
C7 H7 0.95(2) ?
C8 C9 1.476(2) yes
C9 C10 1.389(2) ?
C9 C14 1.398(3) ?
C10 C11 1.383(3) ?
C10 H10 0.9300 ?
C11 C12 1.381(3) ?
C11 H11 0.9300 ?
C12 O3 1.355(2) ?
C12 C13 1.394(3) ?
C13 C14 1.366(3) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 O3 1.433(3) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 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 O2 2_655 0.95(2) 2.51(2) 3.363(3) 149.6(19) yes
C7 H7 O2 2 0.95(2) 2.39(2) 3.274(2) 153.7(17) yes
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
_geom_torsion_publ_flag
O4 N1 C1 C2 -131.6(2) ?
O5 N1 C1 C2 47.3(3) ?
O4 N1 C1 C6 49.4(3) yes
O5 N1 C1 C6 -131.7(2) ?
C6 C1 C2 C3 -0.6(3) ?
N1 C1 C2 C3 -179.6(2) ?
C1 C2 C3 C4 1.5(3) ?
C2 C3 C4 C5 -0.7(3) ?
C3 C4 C5 C6 -1.0(3) ?
C7 O1 C6 C5 15.1(3) yes
C7 O1 C6 C1 -167.31(16) ?
C4 C5 C6 O1 179.50(18) ?
C4 C5 C6 C1 1.9(3) ?
C2 C1 C6 O1 -178.91(17) ?
N1 C1 C6 O1 0.0(3) ?
C2 C1 C6 C5 -1.1(3) ?
N1 C1 C6 C5 177.84(17) ?
C6 O1 C7 C16 158.16(16) ?
C6 O1 C7 C8 -83.09(19) ?
O1 C7 C8 O2 -24.4(2) ?
C16 C7 C8 O2 92.3(2) ?
O1 C7 C8 C9 159.03(14) ?
C16 C7 C8 C9 -84.3(2) ?
O2 C8 C9 C10 164.16(17) yes
C7 C8 C9 C10 -19.4(2) ?
O2 C8 C9 C14 -14.6(3) ?
C7 C8 C9 C14 161.91(16) ?
C14 C9 C10 C11 2.1(3) ?
C8 C9 C10 C11 -176.67(17) ?
C9 C10 C11 C12 -1.6(3) ?
C10 C11 C12 O3 179.72(18) ?
C10 C11 C12 C13 -0.4(3) ?
O3 C12 C13 C14 -178.18(18) ?
C11 C12 C13 C14 1.9(3) ?
C12 C13 C14 C9 -1.5(3) ?
C10 C9 C14 C13 -0.5(3) ?
C8 C9 C14 C13 178.28(17) ?
C11 C12 O3 C15 -0.6(3) yes
C13 C12 O3 C15 179.58(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17404038
