#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/30/2223087.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_2223087
loop_
_publ_author_name
'Babu, Sainath'
'Raghavamenon, Achuthan C.'
'Fronczek, Frank R.'
'Uppu, Rao M.'
_publ_section_title
;
 4-Hydroxy-3-methoxy-5-nitroacetophenone (5-nitroapocynin)
;
_journal_coeditor_code           HB5058
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2292
_journal_page_last               o2293
_journal_paper_doi               10.1107/S160053680903390X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H9 N O5'
_chemical_formula_moiety         'C9 H9 N O5'
_chemical_formula_sum            'C9 H9 N O5'
_chemical_formula_weight         211.17
_chemical_name_systematic
;
4-Hydroxy-3-methoxy-5-nitroacetophenone
;
_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
_cell_angle_beta                 96.485(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6598(10)
_cell_length_b                   16.815(2)
_cell_length_c                   8.0491(11)
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      36.3
_cell_measurement_theta_min      2.5
_cell_volume                     895.6(2)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device
'Nonius KappaCCD diffractometer with Oxford Cryostream'
_diffrn_measurement_method       'ω and φ'
_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  0.025
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22479
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         36.3
_diffrn_reflns_theta_min         2.8
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'golden yellow'
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.062
_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
'calc w=1/[σ²(Fo²)+(0.0585P)²+0.2019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.120
_reflns_number_gt                3226
_reflns_number_total             4255
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5058.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223087
_cod_database_fobs_code          2223087
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
O O1 0.70859(9) 0.17341(4) 0.57565(8) 0.01682(13) Uani d . 1 . .
H H1O 0.805(2) 0.1965(9) 0.5277(18) 0.025 Uiso d . 1 . .
O O2 0.40131(9) 0.12263(4) 0.70993(9) 0.01727(13) Uani d . 1 . .
O O3 0.03482(9) 0.36827(4) 0.88871(9) 0.01850(14) Uani d . 1 . .
O O4 0.90549(10) 0.29612(4) 0.48481(9) 0.02148(15) Uani d . 1 . .
O O5 0.81333(10) 0.41618(4) 0.53665(9) 0.02082(14) Uani d . 1 . .
N N1 0.79036(11) 0.34401(4) 0.54412(9) 0.01483(13) Uani d . 1 . .
C C1 0.32973(11) 0.33924(5) 0.76315(10) 0.01274(14) Uani d . 1 . .
C C2 0.29375(12) 0.25663(5) 0.77082(10) 0.01340(14) Uani d . 1 . .
H H2 0.1831(18) 0.2368(8) 0.8237(15) 0.016 Uiso d . 1 . .
C C3 0.42194(12) 0.20294(5) 0.70775(10) 0.01312(14) Uani d . 1 . .
C C4 0.59325(12) 0.22979(5) 0.63245(10) 0.01309(14) Uani d . 1 . .
C C5 0.62316(11) 0.31230(5) 0.62424(10) 0.01315(14) Uani d . 1 . .
C C6 0.49407(12) 0.36689(5) 0.68977(10) 0.01365(14) Uani d . 1 . .
H H6 0.5227(18) 0.4219(8) 0.6815(15) 0.016 Uiso d . 1 . .
C C7 0.22582(13) 0.09248(5) 0.77728(12) 0.01791(16) Uani d . 1 . .
H H7A 0.2325 0.1066 0.8959 0.027 Uiso calc R 1 . .
H H7B 0.2211 0.0345 0.7654 0.027 Uiso calc R 1 . .
H H7C 0.1041 0.1158 0.7165 0.027 Uiso calc R 1 . .
C C8 0.18762(12) 0.39440(5) 0.83692(10) 0.01404(14) Uani d . 1 . .
C C9 0.23465(14) 0.48181(5) 0.84358(12) 0.01944(17) Uani d . 1 . .
H H9A 0.2105 0.5043 0.7308 0.029 Uiso calc R 1 . .
H H9B 0.3766 0.4897 0.8876 0.029 Uiso calc R 1 . .
H H9C 0.1476 0.5084 0.9167 0.029 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
C4 O1 H1O . . 108.5(10) ?
C3 O2 C7 . . 116.37(7) ?
O5 N1 O4 . . 122.44(7) ?
O5 N1 C5 . . 119.50(7) ?
O4 N1 C5 . . 118.06(7) ?
C6 C1 C2 . . 119.75(7) ?
C6 C1 C8 . . 121.91(7) ?
C2 C1 C8 . . 118.34(7) ?
C3 C2 C1 . . 120.87(7) ?
C3 C2 H2 . . 118.5(8) ?
C1 C2 H2 . . 120.6(8) ?
O2 C3 C2 . . 125.38(7) ?
O2 C3 C4 . . 114.07(7) ?
C2 C3 C4 . . 120.55(7) ?
O1 C4 C5 . . 126.60(7) ?
O1 C4 C3 . . 116.15(7) ?
C5 C4 C3 . . 117.24(7) ?
C6 C5 C4 . . 122.23(7) ?
C6 C5 N1 . . 117.47(7) ?
C4 C5 N1 . . 120.29(7) ?
C1 C6 C5 . . 119.34(8) ?
C1 C6 H6 . . 122.2(7) ?
C5 C6 H6 . . 118.4(7) ?
O2 C7 H7A . . 109.5 ?
O2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O3 C8 C1 . . 120.03(8) ?
O3 C8 C9 . . 121.13(8) ?
C1 C8 C9 . . 118.83(7) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 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
O1 C4 . 1.3330(10) ?
O1 H1O . 0.878(14) ?
O2 C3 . 1.3576(10) ?
O2 C7 . 1.4352(11) ?
O3 C8 . 1.2240(10) ?
O4 N1 . 1.2438(10) ?
O5 N1 . 1.2255(10) ?
N1 C5 . 1.4499(10) ?
C1 C6 . 1.3817(11) ?
C1 C2 . 1.4120(12) ?
C1 C8 . 1.4952(11) ?
C2 C3 . 1.3783(11) ?
C2 H2 . 0.952(12) ?
C3 C4 . 1.4245(11) ?
C4 C5 . 1.4043(12) ?
C5 C6 . 1.4008(11) ?
C6 H6 . 0.948(13) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C9 . 1.5026(12) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
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
O1 H1O O4 . 0.878(14) 1.850(15) 2.5939(10) 141.3(13)
O1 H1O O3 4_665 0.878(14) 2.271(14) 2.8660(9) 124.9(12)
C2 H2 O4 4_466 0.952(12) 2.439(12) 3.3831(12) 171.4(11)
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 . . . . 0.78(12) ?
C8 C1 C2 C3 . . . . -178.74(7) ?
C7 O2 C3 C2 . . . . 2.89(12) ?
C7 O2 C3 C4 . . . . -177.15(7) ?
C1 C2 C3 O2 . . . . 179.60(8) ?
C1 C2 C3 C4 . . . . -0.36(12) ?
O2 C3 C4 O1 . . . . -0.18(10) ?
C2 C3 C4 O1 . . . . 179.78(7) ?
O2 C3 C4 C5 . . . . 179.38(7) ?
C2 C3 C4 C5 . . . . -0.66(12) ?
O1 C4 C5 C6 . . . . -179.19(8) ?
C3 C4 C5 C6 . . . . 1.31(12) ?
O1 C4 C5 N1 . . . . 1.65(13) ?
C3 C4 C5 N1 . . . . -177.86(7) ?
O5 N1 C5 C6 . . . . 0.14(12) ?
O4 N1 C5 C6 . . . . -179.69(7) ?
O5 N1 C5 C4 . . . . 179.34(8) ?
O4 N1 C5 C4 . . . . -0.48(12) ?
C2 C1 C6 C5 . . . . -0.15(12) ?
C8 C1 C6 C5 . . . . 179.35(7) ?
C4 C5 C6 C1 . . . . -0.92(12) ?
N1 C5 C6 C1 . . . . 178.27(7) ?
C6 C1 C8 O3 . . . . 174.11(8) ?
C2 C1 C8 O3 . . . . -6.38(12) ?
C6 C1 C8 C9 . . . . -5.00(12) ?
C2 C1 C8 C9 . . . . 174.51(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 260051
