#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/41/2204160.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_2204160
loop_
_publ_author_name
'Jin Long-Fei'
'Xiao Feng-Ping'
'Wang Cheng-Gang'
_publ_section_title
;
 Methyl 3,5-dinitrosalicylate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1593
_journal_page_last               o1594
_journal_paper_doi               10.1107/S1600536804020331
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C8 H6 N2 O7'
_chemical_formula_moiety         'C8 H6 N2 O7'
_chemical_formula_sum            'C8 H6 N2 O7'
_chemical_formula_weight         242.16
_chemical_name_systematic
;
Methyl 3,5-dinitrosalicylate
;
_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                 96.929(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.459(2)
_cell_length_b                   16.942(5)
_cell_length_c                   6.6832(18)
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.40
_cell_volume                     950.8(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4905
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0628P)²+0.421P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                1520
_reflns_number_total             1869
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6358.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204160
_cod_database_fobs_code          2204160
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
C1 0.6300(2) 0.56515(12) 0.2291(3) 0.0335(5) Uani d . 1 C
C2 0.4663(2) 0.57121(12) 0.2540(3) 0.0342(5) Uani d . 1 C
C3 0.4019(2) 0.64721(12) 0.2561(3) 0.0350(5) Uani d . 1 C
C4 0.4883(3) 0.71403(12) 0.2309(3) 0.0348(5) Uani d . 1 C
H4 0.4428 0.7639 0.2355 0.042 Uiso calc R 1 H
C5 0.6457(2) 0.70485(11) 0.1984(3) 0.0337(5) Uani d . 1 C
C6 0.7172(2) 0.63215(12) 0.1990(3) 0.0339(5) Uani d . 1 C
H6 0.8238 0.6280 0.1793 0.041 Uiso calc R 1 H
C7 0.7065(3) 0.48605(12) 0.2435(3) 0.0387(5) Uani d . 1 C
C8 0.9540(3) 0.41851(15) 0.2634(5) 0.0600(7) Uani d . 1 C
H8A 0.9533 0.3991 0.3982 0.090 Uiso calc R 1 H
H8B 1.0615 0.4292 0.2396 0.090 Uiso calc R 1 H
H8C 0.9086 0.3796 0.1691 0.090 Uiso calc R 1 H
N1 0.2350(2) 0.65921(12) 0.2927(3) 0.0441(5) Uani d . 1 N
N2 0.7398(2) 0.77534(10) 0.1682(3) 0.0386(5) Uani d . 1 N
O1 0.86066(18) 0.49074(9) 0.2382(3) 0.0523(5) Uani d . 1 O
O2 0.6342(2) 0.42520(9) 0.2604(3) 0.0532(5) Uani d . 1 O
O3 0.37768(18) 0.50811(9) 0.2800(3) 0.0486(5) Uani d . 1 O
H3 0.4314 0.4681 0.2735 0.073 Uiso calc R 1 H
O4 0.13718(19) 0.61036(11) 0.2276(3) 0.0669(6) Uani d . 1 O
O5 0.2055(2) 0.71811(11) 0.3858(3) 0.0620(5) Uani d . 1 O
O6 0.6845(2) 0.83945(9) 0.2036(3) 0.0556(5) Uani d . 1 O
O7 0.86876(19) 0.76610(10) 0.1071(3) 0.0522(5) 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 C1 C2 120.22(18) ?
C6 C1 C7 120.98(18) ?
C2 C1 C7 118.76(18) ?
O3 C2 C3 120.83(18) ?
O3 C2 C1 122.08(18) yes
C3 C2 C1 117.06(18) ?
C4 C3 C2 123.04(19) ?
C4 C3 N1 116.25(18) ?
C2 C3 N1 120.68(18) ?
C3 C4 C5 117.70(19) ?
C3 C4 H4 121.1 ?
C5 C4 H4 121.1 ?
C6 C5 C4 122.17(18) ?
C6 C5 N2 119.13(18) ?
C4 C5 N2 118.68(18) ?
C5 C6 C1 119.71(19) ?
C5 C6 H6 120.1 ?
C1 C6 H6 120.1 ?
O2 C7 O1 124.7(2) yes
O2 C7 C1 123.6(2) ?
O1 C7 C1 111.72(18) yes
O1 C8 H8A 109.5 ?
O1 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
O1 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
O4 N1 O5 124.68(19) ?
O4 N1 C3 118.13(19) ?
O5 N1 C3 117.20(18) ?
O6 N2 O7 124.03(18) ?
O6 N2 C5 118.27(18) ?
O7 N2 C5 117.70(17) ?
C7 O1 C8 118.25(18) yes
C2 O3 H3 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.381(3) ?
C1 C2 1.419(3) ?
C1 C7 1.486(3) yes
C2 O3 1.329(2) yes
C2 C3 1.399(3) ?
C3 C4 1.369(3) ?
C3 N1 1.475(3) ?
C4 C5 1.384(3) ?
C4 H4 0.9300 ?
C5 C6 1.372(3) ?
C5 N2 1.463(3) yes
C6 H6 0.9300 ?
C7 O2 1.211(3) yes
C7 O1 1.312(3) yes
C8 O1 1.455(3) yes
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
N1 O4 1.214(3) ?
N1 O5 1.218(2) ?
N2 O6 1.217(2) yes
N2 O7 1.220(2) yes
O3 H3 0.8200 ?
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
O3 H3 O6 2_645 0.82 2.40 2.910(2) 121 yes
O3 H3 O2 . 0.82 1.88 2.602(2) 147 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
C6 C1 C2 O3 178.9(2) ?
C7 C1 C2 O3 -3.4(3) ?
C6 C1 C2 C3 -2.9(3) ?
C7 C1 C2 C3 174.82(19) ?
O3 C2 C3 C4 179.7(2) ?
C1 C2 C3 C4 1.5(3) ?
O3 C2 C3 N1 1.6(3) ?
C1 C2 C3 N1 -176.57(18) ?
C2 C3 C4 C5 1.2(3) ?
N1 C3 C4 C5 179.35(18) ?
C3 C4 C5 C6 -2.6(3) ?
C3 C4 C5 N2 179.14(19) ?
C4 C5 C6 C1 1.3(3) ?
N2 C5 C6 C1 179.48(19) ?
C2 C1 C6 C5 1.6(3) ?
C7 C1 C6 C5 -176.1(2) ?
C6 C1 C7 O2 -176.5(2) ?
C2 C1 C7 O2 5.8(3) ?
C6 C1 C7 O1 4.3(3) ?
C2 C1 C7 O1 -173.42(19) ?
C4 C3 N1 O4 146.9(2) ?
C2 C3 N1 O4 -34.9(3) yes
C4 C3 N1 O5 -32.7(3) ?
C2 C3 N1 O5 145.5(2) yes
C6 C5 N2 O6 -167.0(2) yes
C4 C5 N2 O6 11.2(3) ?
C6 C5 N2 O7 13.6(3) yes
C4 C5 N2 O7 -168.1(2) ?
O2 C7 O1 C8 -3.0(4) yes
C1 C7 O1 C8 176.2(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 81036
