#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221713.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_2221713
loop_
_publ_author_name
'Gao, Lei'
'Guo, Li-hua'
'Liu, Rui'
'Que, Dan-hua'
'Ma, Hong-fei'
_publ_section_title
;
 1-(4-Benzyloxy-5-methoxy-2-nitrophenyl)ethanone
;
_journal_coeditor_code           HK2654
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1005
_journal_paper_doi               10.1107/S1600536809011532
_journal_volume                  65
_journal_year                    2009
_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_name_systematic
;
1-(4-Benzyloxy-5-methoxy-2-nitrophenyl)ethanone
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.390(3)
_cell_length_b                   10.465(2)
_cell_length_c                   20.768(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      0.990
_cell_measurement_theta_min      0.988
_cell_volume                     2910.1(10)
_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  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2634
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0708
_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)+(0.118P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.2225
_reflns_number_gt                1446
_reflns_number_total             2634
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2654.cif
_cod_data_source_block           I
_cod_database_code               2221713
_cod_database_fobs_code          2221713
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
N N 0.4084(2) 0.3120(3) 0.33235(15) 0.0456(8) Uani d . 1 . .
O O1 0.07225(17) 0.1644(3) 0.38239(11) 0.0460(7) Uani d . 1 . .
O O2 0.13768(18) 0.0124(3) 0.46870(13) 0.0538(8) Uani d . 1 . .
O O3 0.5275(2) 0.0290(3) 0.42219(18) 0.0748(10) Uani d . 1 . .
O O4 0.4987(2) 0.2830(3) 0.33126(15) 0.0684(10) Uani d . 1 . .
O O5 0.3740(2) 0.4020(3) 0.30338(14) 0.0633(9) Uani d . 1 . .
C C1 -0.1972(3) 0.0558(5) 0.2841(2) 0.0683(13) Uani d . 1 . .
H H1A -0.2128 -0.0196 0.2626 0.082 Uiso calc R 1 . .
C C2 -0.2731(4) 0.1305(6) 0.3092(3) 0.0793(16) Uani d . 1 . .
H H2A -0.3394 0.1054 0.3051 0.095 Uiso calc R 1 . .
C C3 -0.2488(3) 0.2420(5) 0.3400(3) 0.0682(13) Uani d . 1 . .
H H3A -0.2994 0.2942 0.3558 0.082 Uiso calc R 1 . .
C C4 -0.1506(3) 0.2778(4) 0.3478(2) 0.0546(11) Uani d . 1 . .
H H4A -0.1357 0.3519 0.3706 0.065 Uiso calc R 1 . .
C C5 -0.0736(3) 0.2049(4) 0.32217(18) 0.0461(10) Uani d . 1 . .
C C6 -0.0996(3) 0.0917(4) 0.2906(2) 0.0592(12) Uani d . 1 . .
H H6A -0.0495 0.0399 0.2737 0.071 Uiso calc R 1 . .
C C7 0.0318(3) 0.2420(4) 0.3310(2) 0.0510(10) Uani d . 1 . .
H H7A 0.0690 0.2277 0.2915 0.061 Uiso calc R 1 . .
H H7B 0.0364 0.3318 0.3420 0.061 Uiso calc R 1 . .
C C8 0.1732(3) 0.1672(3) 0.39057(17) 0.0380(9) Uani d . 1 . .
C C9 0.2392(3) 0.2446(4) 0.35806(18) 0.0428(9) Uani d . 1 . .
H H9A 0.2159 0.3038 0.3282 0.051 Uiso calc R 1 . .
C C10 0.3402(2) 0.2336(4) 0.37010(17) 0.0409(9) Uani d . 1 . .
C C11 0.3807(3) 0.1481(4) 0.41517(18) 0.0430(9) Uani d . 1 . .
C C12 0.3098(3) 0.0707(4) 0.44838(19) 0.0478(10) Uani d . 1 . .
H H12A 0.3323 0.0118 0.4786 0.057 Uiso calc R 1 . .
C C13 0.2105(3) 0.0807(4) 0.43705(18) 0.0422(9) Uani d . 1 . .
C C14 0.1676(3) -0.0629(5) 0.5236(2) 0.0661(13) Uani d . 1 . .
H H14A 0.1103 -0.1054 0.5413 0.099 Uiso calc R 1 . .
H H14B 0.1964 -0.0080 0.5557 0.099 Uiso calc R 1 . .
H H14C 0.2160 -0.1253 0.5104 0.099 Uiso calc R 1 . .
C C15 0.4875(3) 0.1311(4) 0.43162(19) 0.0478(10) Uani d . 1 . .
C C16 0.5384(3) 0.2346(5) 0.4663(2) 0.0652(13) Uani d . 1 . .
H H16A 0.6068 0.2115 0.4735 0.098 Uiso calc R 1 . .
H H16B 0.5059 0.2486 0.5069 0.098 Uiso calc R 1 . .
H H16C 0.5356 0.3115 0.4411 0.098 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 0.0016 '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
O5 N O4 . . 123.3(3) ?
O5 N C10 . . 117.9(3) ?
O4 N C10 . . 118.7(3) ?
C8 O1 C7 . . 116.8(3) ?
C13 O2 C14 . . 117.7(3) ?
C6 C1 C2 . . 120.6(5) ?
C6 C1 H1A . . 119.7 ?
C2 C1 H1A . . 119.7 ?
C3 C2 C1 . . 118.9(4) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C2 C3 C4 . . 120.9(5) ?
C2 C3 H3A . . 119.5 ?
C4 C3 H3A . . 119.5 ?
C3 C4 C5 . . 120.9(4) ?
C3 C4 H4A . . 119.5 ?
C5 C4 H4A . . 119.5 ?
C4 C5 C6 . . 117.4(4) ?
C4 C5 C7 . . 121.2(4) ?
C6 C5 C7 . . 121.3(4) ?
C1 C6 C5 . . 121.1(4) ?
C1 C6 H6A . . 119.4 ?
C5 C6 H6A . . 119.4 ?
O1 C7 C5 . . 107.6(3) ?
O1 C7 H7A . . 110.2 ?
C5 C7 H7A . . 110.2 ?
O1 C7 H7B . . 110.2 ?
C5 C7 H7B . . 110.2 ?
H7A C7 H7B . . 108.5 ?
O1 C8 C9 . . 126.0(3) ?
O1 C8 C13 . . 115.0(3) ?
C9 C8 C13 . . 119.0(3) ?
C8 C9 C10 . . 119.4(3) ?
C8 C9 H9A . . 120.3 ?
C10 C9 H9A . . 120.3 ?
C9 C10 C11 . . 123.5(3) ?
C9 C10 N . . 118.0(3) ?
C11 C10 N . . 118.4(3) ?
C10 C11 C12 . . 115.3(3) ?
C10 C11 C15 . . 127.1(3) ?
C12 C11 C15 . . 117.6(3) ?
C13 C12 C11 . . 121.7(4) ?
C13 C12 H12A . . 119.1 ?
C11 C12 H12A . . 119.1 ?
C12 C13 O2 . . 124.9(4) ?
C12 C13 C8 . . 121.0(3) ?
O2 C13 C8 . . 114.1(3) ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O3 C15 C16 . . 121.6(4) ?
O3 C15 C11 . . 119.7(4) ?
C16 C15 C11 . . 118.2(4) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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
N O5 . 1.209(4) ?
N O4 . 1.247(4) ?
N C10 . 1.456(5) ?
O1 C8 . 1.363(4) ?
O1 C7 . 1.446(4) ?
O2 C13 . 1.376(4) ?
O2 C14 . 1.443(5) ?
O3 C15 . 1.212(5) ?
C1 C6 . 1.367(5) ?
C1 C2 . 1.384(7) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.370(7) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.377(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.389(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.398(6) ?
C5 C7 . 1.475(5) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.376(5) ?
C8 C13 . 1.414(5) ?
C9 C10 . 1.380(5) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.404(5) ?
C11 C12 . 1.426(5) ?
C11 C15 . 1.480(5) ?
C12 C13 . 1.355(5) ?
C12 H12A . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C16 . 1.468(6) ?
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
C4 H4A O3 8_665 0.93 2.58 3.466(5) 158 yes
C16 H16C O4 . 0.96 2.35 2.899(5) 115 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_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 C3 . . . . 0.8(8) ?
C1 C2 C3 C4 . . . . -2.0(8) ?
C2 C3 C4 C5 . . . . 2.9(7) ?
C3 C4 C5 C6 . . . . -2.5(6) ?
C3 C4 C5 C7 . . . . -179.4(4) ?
C2 C1 C6 C5 . . . . -0.5(7) ?
C4 C5 C6 C1 . . . . 1.3(6) ?
C7 C5 C6 C1 . . . . 178.1(4) ?
C8 O1 C7 C5 . . . . 168.6(3) ?
C4 C5 C7 O1 . . . . 100.4(4) ?
C6 C5 C7 O1 . . . . -76.4(5) ?
C7 O1 C8 C9 . . . . 5.7(5) ?
C7 O1 C8 C13 . . . . -174.0(3) ?
O1 C8 C9 C10 . . . . -177.9(3) ?
C13 C8 C9 C10 . . . . 1.9(5) ?
C8 C9 C10 C11 . . . . -1.1(6) ?
C8 C9 C10 N . . . . 176.7(3) ?
O5 N C10 C9 . . . . 16.4(5) ?
O4 N C10 C9 . . . . -163.3(3) ?
O5 N C10 C11 . . . . -165.6(3) ?
O4 N C10 C11 . . . . 14.6(5) ?
C9 C10 C11 C12 . . . . 0.4(5) ?
N C10 C11 C12 . . . . -177.4(3) ?
C9 C10 C11 C15 . . . . -179.2(4) ?
N C10 C11 C15 . . . . 3.0(6) ?
C10 C11 C12 C13 . . . . -0.4(6) ?
C15 C11 C12 C13 . . . . 179.2(4) ?
C11 C12 C13 O2 . . . . -177.7(3) ?
C11 C12 C13 C8 . . . . 1.3(6) ?
C14 O2 C13 C12 . . . . 8.6(6) ?
C14 O2 C13 C8 . . . . -170.5(4) ?
O1 C8 C13 C12 . . . . 177.8(4) ?
C9 C8 C13 C12 . . . . -2.0(6) ?
O1 C8 C13 O2 . . . . -3.1(5) ?
C9 C8 C13 O2 . . . . 177.1(3) ?
C10 C11 C15 O3 . . . . -118.1(5) ?
C12 C11 C15 O3 . . . . 62.3(5) ?
C10 C11 C15 C16 . . . . 69.2(5) ?
C12 C11 C15 C16 . . . . -110.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742068
