#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/94/2209420.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_2209420
loop_
_publ_author_name
'Behrman, David M.'
'Behrman, E. J.'
'Parkin, Sean'
_publ_section_title
;
 2-Methoxy-3-nitrophenol
;
_journal_coeditor_code           BT2114
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3119
_journal_page_last               o3121
_journal_paper_doi               10.1107/S1600536806023713
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H7 N O4'
_chemical_formula_moiety         'C7 H7 N O4'
_chemical_formula_sum            'C7 H7 N O4'
_chemical_formula_weight         169.14
_chemical_melting_point          342
_chemical_name_common            6-nitroguaiacol
_chemical_name_systematic        2-methoxy-3-nitrophenol
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   13.9581(2)
_cell_length_b                   13.1337(6)
_cell_length_c                   4.0110(7)
_cell_measurement_reflns_used    1032
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     735.30(13)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELXL97 and local procedures'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            1613
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         .243
_refine_diff_density_min         -.261
_refine_ls_extinction_coef       0.017(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         958
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0636P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                751
_reflns_number_total             958
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2114.cif
_cod_data_source_block           I
_cod_database_code               2209420
_cod_database_fobs_code          2209420
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, 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
O O2 0.12248(12) 0.35260(12) 0.7043(5) 0.0201(5) Uani d . 1
O O1 -0.03621(12) 0.44005(11) 0.4343(6) 0.0222(5) Uani d . 1
H H1 -0.0030 0.4596 0.5969 0.033 Uiso calc R 1
O O3 0.15196(13) 0.04575(13) 0.6390(6) 0.0315(6) Uani d . 1
O O4 0.23431(12) 0.18489(14) 0.6469(7) 0.0338(6) Uani d . 1
N N1 0.16092(15) 0.13741(16) 0.5860(7) 0.0221(6) Uani d . 1
C C2 0.06553(16) 0.29504(18) 0.5018(7) 0.0166(6) Uani d . 1
C C4 0.01458(18) 0.13440(17) 0.2551(8) 0.0202(7) Uani d . 1
H H4 0.0247 0.0636 0.2217 0.024 Uiso calc R 1
C C6 -0.08061(16) 0.28544(19) 0.1778(7) 0.0197(6) Uani d . 1
H H6 -0.1354 0.3179 0.0858 0.024 Uiso calc R 1
C C3 0.07886(17) 0.19133(17) 0.4409(8) 0.0178(6) Uani d . 1
C C1 -0.01693(16) 0.33979(17) 0.3694(7) 0.0172(6) Uani d . 1
C C5 -0.06418(17) 0.1821(2) 0.1195(8) 0.0222(7) Uani d . 1
H H5 -0.1076 0.1444 -0.0147 0.027 Uiso calc R 1
C C7 0.19481(17) 0.4112(2) 0.5294(8) 0.0249(7) Uani d . 1
H H7A 0.2417 0.3648 0.4293 0.037 Uiso calc R 1
H H7B 0.2273 0.4566 0.6868 0.037 Uiso calc R 1
H H7C 0.1643 0.4517 0.3538 0.037 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0213(9) 0.0204(9) 0.0186(12) -0.0042(7) 0.0012(9) 0.0012(9)
O1 0.0256(9) 0.0168(8) 0.0242(12) 0.0034(7) -0.0040(9) 0.0001(9)
O3 0.0360(10) 0.0155(9) 0.0431(15) 0.0048(8) -0.0026(12) 0.0057(10)
O4 0.0211(9) 0.0286(10) 0.0517(17) 0.0010(8) -0.0073(12) 0.0061(12)
N1 0.0229(11) 0.0217(12) 0.0218(14) 0.0025(9) 0.0014(11) -0.0002(11)
C2 0.0182(12) 0.0157(12) 0.0159(16) -0.0026(9) 0.0017(11) -0.0014(12)
C4 0.0243(13) 0.0154(12) 0.0208(18) -0.0022(10) 0.0072(13) 0.0012(12)
C6 0.0185(11) 0.0220(12) 0.0188(17) 0.0012(10) 0.0014(13) 0.0055(13)
C3 0.0185(12) 0.0165(12) 0.0184(15) 0.0036(10) 0.0018(12) 0.0007(13)
C1 0.0211(12) 0.0134(11) 0.0170(17) -0.0016(10) 0.0048(13) 0.0013(12)
C5 0.0239(13) 0.0251(13) 0.0175(16) -0.0066(10) 0.0019(13) -0.0035(13)
C7 0.0225(13) 0.0215(14) 0.0306(19) -0.0050(11) -0.0001(14) 0.0008(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 '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
C2 O2 C7 114.3(2)
C1 O1 H1 109.5
O4 N1 O3 123.4(2)
O4 N1 C3 119.1(2)
O3 N1 C3 117.5(2)
O2 C2 C3 124.5(2)
O2 C2 C1 118.2(2)
C3 C2 C1 117.0(2)
C5 C4 C3 118.9(2)
C5 C4 H4 120.5
C3 C4 H4 120.5
C1 C6 C5 119.5(2)
C1 C6 H6 120.3
C5 C6 H6 120.3
C4 C3 C2 122.3(2)
C4 C3 N1 117.3(2)
C2 C3 N1 120.4(2)
O1 C1 C6 118.6(2)
O1 C1 C2 119.6(2)
C6 C1 C2 121.8(2)
C4 C5 C6 120.5(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C2 1.365(3)
O2 C7 1.450(3)
O1 C1 1.369(3)
O1 H1 0.8400
O3 N1 1.229(3)
O4 N1 1.224(3)
N1 C3 1.467(3)
C2 C3 1.396(3)
C2 C1 1.397(3)
C4 C5 1.377(4)
C4 C3 1.385(4)
C4 H4 0.9500
C6 C1 1.375(4)
C6 C5 1.396(4)
C6 H6 0.9500
C5 H5 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 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 H1 O1 2_565 0.84 1.97 2.743(2) 153.2
O1 H1 O2 . 0.84 2.29 2.720(2) 112.4
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
C7 O2 C2 C3 98.2(3)
C7 O2 C2 C1 -88.0(3)
C5 C4 C3 C2 1.4(4)
C5 C4 C3 N1 179.0(3)
O2 C2 C3 C4 174.6(3)
C1 C2 C3 C4 0.7(4)
O2 C2 C3 N1 -2.9(4)
C1 C2 C3 N1 -176.7(2)
O4 N1 C3 C4 154.6(3)
O3 N1 C3 C4 -25.2(4)
O4 N1 C3 C2 -27.8(4)
O3 N1 C3 C2 152.4(3)
C5 C6 C1 O1 -177.5(3)
C5 C6 C1 C2 1.6(4)
O2 C2 C1 O1 2.6(4)
C3 C2 C1 O1 176.9(3)
O2 C2 C1 C6 -176.5(2)
C3 C2 C1 C6 -2.2(4)
C3 C4 C5 C6 -2.1(4)
C1 C6 C5 C4 0.6(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10640685
