#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/43/2214310.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_2214310
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'M. Venkatraj'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
;
 Methyl 2,6-dihydroxy-3-nitrobenzoate
;
_journal_coeditor_code           LH2413
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3227
_journal_page_last               o3227
_journal_paper_doi               10.1107/S1600536807028589
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H7 N O6'
_chemical_formula_moiety         'C8 H7 N O6'
_chemical_formula_sum            'C8 H7 N O6'
_chemical_formula_weight         213.15
_chemical_name_systematic
;
Methyl 2,6-dihydroxy-3-nitrobenzoate
;
_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                 91.682(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8681(2)
_cell_length_b                   18.3596(5)
_cell_length_c                   12.0186(9)
_cell_measurement_reflns_used    3726
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     853.15(8)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1995)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 1997) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7208
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut wedge'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         .366
_refine_diff_density_min         -.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0907P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                1277
_reflns_number_total             1922
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2413.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214310
_cod_database_fobs_code          2214310
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
N N1 0.1783(4) 0.09134(8) 0.62514(12) 0.0410(4) Uani d . 1
O O1 0.2648(4) 0.02998(7) 0.59892(13) 0.0726(6) Uani d . 1
O O2 0.0072(4) 0.10261(7) 0.70927(11) 0.0494(4) Uani d . 1
O O3 0.0305(3) 0.24073(6) 0.67916(9) 0.0384(4) Uani d . 1
H H3 -0.0207 0.2028 0.7123 0.058 Uiso calc R 1
O O4 0.5981(3) 0.31416(7) 0.35145(9) 0.0424(4) Uani d . 1
H H4 0.5587 0.3551 0.3776 0.064 Uiso calc R 1
O O5 0.3713(3) 0.40744(7) 0.48250(11) 0.0480(4) Uani d . 1
O O6 0.1204(3) 0.37470(6) 0.63917(10) 0.0431(4) Uani d . 1
C C1 0.2763(4) 0.15166(9) 0.55705(14) 0.0330(4) Uani d . 1
C C2 0.2024(4) 0.22407(9) 0.58833(13) 0.0299(4) Uani d . 1
C C3 0.3148(4) 0.28084(9) 0.51908(13) 0.0296(4) Uani d . 1
C C4 0.4839(4) 0.26314(9) 0.42013(14) 0.0327(4) Uani d . 1
C C5 0.5425(4) 0.19083(10) 0.39009(13) 0.0381(5) Uani d . 1
H H5 0.6501 0.1800 0.3229 0.046 Uiso calc R 1
C C6 0.4435(5) 0.13631(10) 0.45810(15) 0.0381(5) Uani d . 1
H H6 0.4875 0.0877 0.4386 0.046 Uiso calc R 1
C C7 0.2707(4) 0.35928(9) 0.54468(14) 0.0331(4) Uani d . 1
C C8 0.0837(6) 0.45169(10) 0.66481(18) 0.0508(5) Uani d . 1
H H8A 0.3085 0.4750 0.6636 0.076 Uiso calc R 1
H H8B -0.0118 0.4571 0.7381 0.076 Uiso calc R 1
H H8C -0.0702 0.4743 0.6098 0.076 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
N1 0.0555(10) 0.0268(9) 0.0413(9) 0.0013(7) 0.0126(7) 0.0011(6)
O1 0.1201(14) 0.0253(8) 0.0751(11) 0.0110(8) 0.0504(10) 0.0036(7)
O2 0.0724(9) 0.0349(8) 0.0423(8) 0.0001(6) 0.0246(7) 0.0034(6)
O3 0.0526(8) 0.0294(7) 0.0341(7) 0.0010(6) 0.0166(6) 0.0004(5)
O4 0.0549(8) 0.0333(8) 0.0399(7) -0.0008(6) 0.0171(6) 0.0045(6)
O5 0.0657(9) 0.0287(7) 0.0506(8) -0.0012(6) 0.0175(7) 0.0038(6)
O6 0.0600(9) 0.0269(7) 0.0432(8) 0.0044(6) 0.0157(6) -0.0038(5)
C1 0.0398(10) 0.0260(9) 0.0334(9) 0.0016(7) 0.0074(7) 0.0015(7)
C2 0.0316(9) 0.0300(9) 0.0284(8) 0.0020(7) 0.0042(7) -0.0015(7)
C3 0.0319(9) 0.0260(9) 0.0311(8) 0.0013(7) 0.0033(7) -0.0006(7)
C4 0.0341(10) 0.0319(10) 0.0325(9) -0.0008(7) 0.0047(7) 0.0023(7)
C5 0.0441(10) 0.0376(11) 0.0331(9) 0.0050(8) 0.0102(7) -0.0027(8)
C6 0.0449(10) 0.0296(10) 0.0403(10) 0.0056(8) 0.0079(8) -0.0040(8)
C7 0.0360(9) 0.0287(10) 0.0348(9) 0.0002(7) 0.0053(7) 0.0003(7)
C8 0.0679(13) 0.0267(11) 0.0588(12) 0.0040(9) 0.0170(10) -0.0077(9)
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'
N N .0061 .0033 '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'
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
O1 N1 O2 121.40(15) ?
O1 N1 C1 119.13(15) ?
O2 N1 C1 119.47(14) ?
C2 O3 H3 109.5 ?
C4 O4 H4 109.5 ?
C7 O6 C8 116.01(14) ?
C6 C1 C2 121.19(15) ?
C6 C1 N1 117.76(15) n
C2 C1 N1 121.04(14) n
O3 C2 C3 118.97(14) n
O3 C2 C1 122.98(14) n
C3 C2 C1 118.04(14) ?
C2 C3 C4 119.04(15) ?
C2 C3 C7 123.75(14) n
C4 C3 C7 117.20(15) n
O4 C4 C5 116.69(14) n
O4 C4 C3 122.02(15) n
C5 C4 C3 121.29(15) ?
C6 C5 C4 119.73(15) ?
C6 C5 H5 120.1 ?
C4 C5 H5 120.1 ?
C5 C6 C1 120.65(16) ?
C5 C6 H6 119.7 ?
C1 C6 H6 119.7 ?
O5 C7 O6 121.58(16) ?
O5 C7 C3 122.15(15) ?
O6 C7 C3 116.27(14) ?
O6 C8 H8A 109.5 ?
O6 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
O6 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 O1 1.2192(19) ?
N1 O2 1.2420(17) ?
N1 C1 1.435(2) ?
O3 C2 1.3306(19) n
O3 H3 0.8300 ?
O4 C4 1.3323(19) ?
O4 H4 0.8300 ?
O5 C7 1.228(2) n
O6 C7 1.322(2) n
O6 C8 1.455(2) ?
C1 C6 1.399(2) ?
C1 C2 1.413(2) ?
C2 C3 1.410(2) ?
C3 C4 1.412(2) ?
C3 C7 1.483(2) n
C4 C5 1.396(2) ?
C5 C6 1.355(2) ?
C5 H5 0.9400 ?
C6 H6 0.9400 ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C8 H8C 0.9700 ?
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
O3 H3 O2 . 0.83 1.84 2.5636(16) 144.5
O3 H3 O4 4_466 0.83 2.28 2.8816(15) 129.4
O3 H3 N1 . 0.83 2.43 2.8797(19) 114.6
O4 H4 O5 . 0.83 1.76 2.5028(16) 148.3
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
O1 N1 C1 C6 5.2(3) ?
O2 N1 C1 C6 -174.73(15) n
O1 N1 C1 C2 -175.62(16) n
O2 N1 C1 C2 4.5(3) ?
C6 C1 C2 O3 176.93(16) ?
N1 C1 C2 O3 -2.3(3) ?
C6 C1 C2 C3 -2.6(3) ?
N1 C1 C2 C3 178.25(15) ?
O3 C2 C3 C4 -177.25(14) ?
C1 C2 C3 C4 2.3(2) ?
O3 C2 C3 C7 3.7(2) ?
C1 C2 C3 C7 -176.80(15) ?
C2 C3 C4 O4 -179.62(15) ?
C7 C3 C4 O4 -0.5(2) ?
C2 C3 C4 C5 -0.2(2) ?
C7 C3 C4 C5 178.90(15) ?
O4 C4 C5 C6 177.77(15) ?
C3 C4 C5 C6 -1.7(3) ?
C4 C5 C6 C1 1.4(3) ?
C2 C1 C6 C5 0.7(3) ?
N1 C1 C6 C5 179.95(16) ?
C8 O6 C7 O5 -0.3(3) ?
C8 O6 C7 C3 178.90(14) ?
C2 C3 C7 O5 -179.95(16) ?
C4 C3 C7 O5 1.0(3) ?
C2 C3 C7 O6 0.9(2) ?
C4 C3 C7 O6 -178.18(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124132
2 PubChem 69508249
