#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/19/8101975.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8101975
loop_
_publ_author_name
'Yu, W.'
'Zhang, T.-L.'
'Yang, L.'
'Zhang, J.-G.'
'Wu, R.-F.'
'Ren, F.-J.'
'Guo, J.-Y.'
'Liu, L.-H.'
_publ_section_title
;
Crystal structure of 2-nitrobenzene-1,4-dioxyacetic acid dihydrate, 
C₆H₃(NO₂)(OCH₂COOH)₂ · 2H₂O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              229
_journal_page_last               230
_journal_volume                  221
_journal_year                    2006
_chemical_formula_structural     'C10H9NO8 &#x00B7; 2H2O'
_chemical_formula_sum            'C10 H13 N O10'
_chemical_formula_weight         307.21
_chemical_name_systematic
; 
 2-nitro-benzene-1,4-dioxyacetic acid dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.907(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3506(16)
_cell_length_b                   22.077(5)
_cell_length_c                   8.1290(17)
_cell_measurement_reflns_used    1490
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.06
_cell_measurement_theta_min      2.96
_cell_volume                     1299.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       phi/omega
_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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6526
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.789326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0013(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0406
_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)+(0.0480P)²+0.0970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1392
_reflns_number_total             2290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1783.cff
_cod_data_source_block           60106b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P12(1)/n1
_cod_database_code               8101975
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1746(2) 0.16643(8) 1.12736(19) 0.0451(5) Uani 1 4 e d . . .
O2 O 0.2534(2) 0.22072(8) 1.4175(2) 0.0451(5) Uani 1 4 e d . . .
O3 O -0.0444(2) 0.23203(7) 1.4342(2) 0.0460(5) Uani 1 4 e d . . .
H3 H -0.0026 0.2502 1.5205 0.055 Uiso 1 4 e calc R . .
O4 O -0.3250(3) 0.15782(10) 0.6239(2) 0.0671(6) Uani 1 4 e d . . .
O5 O -0.2429(3) 0.08465(10) 0.4790(3) 0.0691(7) Uani 1 4 e d . . .
O6 O 0.1125(2) 0.08123(7) 0.48022(19) 0.0411(5) Uani 1 4 e d . . .
O7 O 0.0723(3) 0.02433(9) 0.1879(2) 0.0569(6) Uani 1 4 e d . . .
O8 O 0.3731(2) 0.00902(9) 0.2103(2) 0.0582(6) Uani 1 4 e d . . .
H8 H 0.3416 -0.0095 0.1226 0.070 Uiso 1 4 e calc R . .
N1 N -0.2098(3) 0.12074(10) 0.5937(3) 0.0426(6) Uani 1 4 e d . . .
C1 C 0.1460(3) 0.14563(11) 0.9652(3) 0.0356(6) Uani 1 4 e d . . .
C2 C -0.0204(3) 0.14364(10) 0.8607(3) 0.0344(6) Uani 1 4 e d . . .
H2 H -0.1270 0.1570 0.8966 0.041 Uiso 1 4 e calc R . .
C3 C -0.0284(3) 0.12124(10) 0.6993(3) 0.0316(6) Uani 1 4 e d . . .
C4 C 0.1291(3) 0.10115(10) 0.6412(3) 0.0315(6) Uani 1 4 e d . . .
C5 C 0.2949(3) 0.10526(11) 0.7499(3) 0.0389(6) Uani 1 4 e d . . .
H5 H 0.4028 0.0933 0.7140 0.047 Uiso 1 4 e calc R . .
C6 C 0.3047(3) 0.12658(11) 0.9095(3) 0.0387(6) Uani 1 4 e d . . .
H6 H 0.4181 0.1283 0.9807 0.046 Uiso 1 4 e calc R . .
C7 C 0.0202(3) 0.18954(11) 1.1899(3) 0.0380(6) Uani 1 4 e d . . .
H7A H -0.0678 0.1575 1.1986 0.046 Uiso 1 4 e calc R . .
H7B H -0.0409 0.2207 1.1163 0.046 Uiso 1 4 e calc R . .
C8 C 0.0927(3) 0.21532(10) 1.3581(3) 0.0331(6) Uani 1 4 e d . . .
C9 C 0.2776(3) 0.06012(11) 0.4292(3) 0.0402(6) Uani 1 4 e d . . .
H9A H 0.3405 0.0315 0.5102 0.048 Uiso 1 4 e calc R . .
H9B H 0.3601 0.0938 0.4205 0.048 Uiso 1 4 e calc R . .
C10 C 0.2241(4) 0.03017(11) 0.2635(3) 0.0394(6) Uani 1 4 e d . . .
O9 O 0.0575(4) 0.28528(10) 0.7246(3) 0.0516(6) Uani 1 4 e d . . .
H9A H -0.034(5) 0.2880(14) 0.776(4) 0.082(12) Uiso 1 4 e d . . .
H9B H 0.145(5) 0.2748(14) 0.790(4) 0.075(13) Uiso 1 4 e d . . .
O10 O 0.2912(3) 0.95107(10) 0.9264(3) 0.0596(6) Uani 1 4 e d . . .
H10A H 0.161(5) 0.9603(12) 0.872(4) 0.076(10) Uiso 1 4 e d . . .
H10B H 0.357(6) 0.9501(16) 0.857(5) 0.107(16) Uiso 1 4 e d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 117.63(18) . . ?
C8 O3 H3 109.5 . . ?
C4 O6 C9 116.31(18) . . ?
C10 O8 H8 109.5 . . ?
O5 N1 O4 122.2(2) . . ?
O5 N1 C3 119.9(2) . . ?
O4 N1 C3 117.9(2) . . ?
C2 C1 O1 125.4(2) . . ?
C2 C1 C6 120.1(2) . . ?
O1 C1 C6 114.5(2) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 N1 121.8(2) . . ?
C2 C3 N1 116.3(2) . . ?
O6 C4 C5 124.0(2) . . ?
O6 C4 C3 118.9(2) . . ?
C5 C4 C3 117.0(2) . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 C8 106.5(2) . . ?
O1 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
O1 C7 H7B 110.4 . . ?
C8 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
O2 C8 O3 124.0(2) . . ?
O2 C8 C7 125.2(2) . . ?
O3 C8 C7 110.7(2) . . ?
O6 C9 C10 107.6(2) . . ?
O6 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O6 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
O7 C10 O8 123.2(2) . . ?
O7 C10 C9 126.5(2) . . ?
O8 C10 C9 110.2(2) . . ?
H9A O9 H9B 108(3) . . ?
H10A O10 H10B 110(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.378(3) . ?
O1 C7 1.416(3) . ?
O2 C8 1.202(3) . ?
O3 C8 1.322(3) . ?
O3 H3 0.8200 . ?
O4 N1 1.232(3) . ?
O5 N1 1.218(3) . ?
O6 C4 1.366(3) . ?
O6 C9 1.426(3) . ?
O7 C10 1.184(3) . ?
O8 C10 1.329(3) . ?
O8 H8 0.8200 . ?
N1 C3 1.457(3) . ?
C1 C2 1.365(3) . ?
C1 C6 1.387(3) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.370(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.492(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.491(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O9 H9A 0.86(3) . ?
O9 H9B 0.79(3) . ?
O10 H10A 1.00(3) . ?
O10 H10B 0.80(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O9 0.82 1.82 2.628(3) 170.6 1_556
O8 H8 O10 0.82 1.80 2.617(3) 175.3 1_544
O9 H9A O2 0.86(3) 2.10(3) 2.946(3) 170(3) 4_565
O9 H9B O3 0.79(3) 2.39(4) 3.146(3) 161(3) 4_665
O10 H10A O7 1.00(3) 1.73(3) 2.728(3) 170(3) 3_566
O10 H10B O8 0.80(4) 2.33(4) 3.008(3) 143(4) 3_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28573416
2 PubChem 71445212
