#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/37/2203712.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_2203712
loop_
_publ_author_name
'Vande Velde, Christophe M. L.'
'Geise, Herman J.'
'Blockhuys, Frank'
_publ_section_title
;
 2,4,5-Trimethoxy-1-nitrobenzene: a structure in the rare space group
 P4₂
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1031
_journal_page_last               o1033
_journal_paper_doi               10.1107/S1600536804011651
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C9 H11 N O5'
_chemical_formula_moiety         'C9 H11 N O5'
_chemical_formula_sum            'C9 H11 N O5'
_chemical_formula_weight         213.19
_chemical_name_common            tmeonitb
_chemical_name_systematic
;
2,4,5-trimethoxy-1-nitrobenzene
;
_space_group_IT_number           77
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4c'
_symmetry_space_group_name_H-M   'P 42'
_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                   15.749(9)
_cell_length_b                   15.749(7)
_cell_length_c                   3.900(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.52
_cell_measurement_theta_min      5.78
_cell_volume                     967.3(9)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius MACH3'
_diffrn_measurement_method       ω/2θ
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5058
_diffrn_reflns_theta_full        31.98
_diffrn_reflns_theta_max         31.98
_diffrn_reflns_theta_min         1.29
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow-green
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1895
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0635P)²+0.0428P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                1070
_reflns_number_total             1895
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6459.cif
_cod_data_source_block           I
_cod_database_code               2203712
_cod_database_fobs_code          2203712
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, 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_occupancy
_atom_site_type_symbol
O4 0.37385(9) 0.36342(9) 0.0676(6) 0.0536(5) Uani d 1 O
O3 0.40971(9) 0.20815(9) 0.2237(7) 0.0526(5) Uani d 1 O
O1 0.11847(10) 0.15313(9) 0.5403(6) 0.0567(6) Uani d 1 O
C1 0.16345(12) 0.28879(12) 0.3483(6) 0.0393(5) Uani d 1 C
N1 0.07951(11) 0.32485(12) 0.3891(8) 0.0520(6) Uani d 1 N
C2 0.18201(12) 0.20482(13) 0.4324(7) 0.0418(5) Uani d 1 C
C5 0.30810(12) 0.31550(12) 0.1837(7) 0.0399(5) Uani d 1 C
C7 0.13922(18) 0.06909(15) 0.6428(10) 0.0557(7) Uani d 1 C
H7A 0.169(2) 0.0376(19) 0.456(13) 0.084 Uiso d 1 H
H7B 0.0879(19) 0.0444(19) 0.713(13) 0.084 Uiso d 1 H
H7C 0.177(2) 0.069(2) 0.838(12) 0.084 Uiso d 1 H
C3 0.26559(13) 0.17736(13) 0.3936(8) 0.0430(6) Uani d 1 C
H3 0.2795(14) 0.1212(14) 0.452(9) 0.052 Uiso d 1 H
C4 0.32791(12) 0.23069(13) 0.2712(7) 0.0413(6) Uani d 1 C
O5 0.02629(12) 0.28761(11) 0.5549(10) 0.0944(10) Uani d 1 O
O6 0.06519(11) 0.39379(13) 0.2601(10) 0.0896(10) Uani d 1 O
C9 0.35461(16) 0.44731(14) -0.0422(9) 0.0523(7) Uani d 1 C
H9A 0.3096(18) 0.4498(19) -0.229(12) 0.078 Uiso d 1 H
H9B 0.4082(18) 0.4686(18) -0.119(11) 0.078 Uiso d 1 H
H9C 0.3319(19) 0.482(2) 0.151(11) 0.078 Uiso d 1 H
C8 0.43519(17) 0.12489(17) 0.3327(11) 0.0587(8) Uani d 1 C
H8A 0.423(2) 0.117(2) 0.582(12) 0.088 Uiso d 1 H
H8B 0.4971(19) 0.1227(19) 0.268(11) 0.088 Uiso d 1 H
H8C 0.403(2) 0.080(2) 0.186(12) 0.088 Uiso d 1 H
C6 0.22654(13) 0.34291(13) 0.2232(8) 0.0413(5) Uani d 1 C
H6 0.2113(14) 0.3998(14) 0.165(9) 0.050 Uiso d 1 H
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
C5 O4 C9 117.01(16)
C4 O3 C8 117.81(19)
C2 O1 C7 118.46(18)
C2 C1 C6 120.80(18)
C2 C1 N1 122.55(18)
C6 C1 N1 116.64(18)
O5 N1 O6 121.6(2)
O5 N1 C1 120.1(2)
O6 N1 C1 118.3(2)
O1 C2 C3 122.96(19)
O1 C2 C1 119.18(17)
C3 C2 C1 117.85(18)
O4 C5 C6 125.41(18)
O4 C5 C4 115.92(17)
C6 C5 C4 118.67(19)
O1 C7 H7A 111(2)
O1 C7 H7B 105.7(19)
H7A C7 H7B 114(3)
O1 C7 H7C 111.7(19)
H7A C7 H7C 107(3)
H7B C7 H7C 107(4)
C4 C3 C2 121.4(2)
C4 C3 H3 119.5(14)
C2 C3 H3 119.1(14)
O3 C4 C3 124.58(19)
O3 C4 C5 115.24(18)
C3 C4 C5 120.18(18)
O4 C9 H9A 113.6(17)
O4 C9 H9B 103.5(18)
H9A C9 H9B 112(3)
O4 C9 H9C 111(2)
H9A C9 H9C 106(2)
H9B C9 H9C 111(3)
O3 C8 H8A 110(2)
O3 C8 H8B 103.1(18)
H8A C8 H8B 116(3)
O3 C8 H8C 108.6(19)
H8A C8 H8C 111(3)
H8B C8 H8C 108(3)
C5 C6 C1 121.07(19)
C5 C6 H6 120.4(14)
C1 C6 H6 118.5(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C5 1.359(3)
O4 C9 1.421(3)
O3 C4 1.349(2)
O3 C8 1.436(3)
O1 C2 1.357(3)
O1 C7 1.421(3)
C1 C2 1.393(3)
C1 C6 1.397(3)
C1 N1 1.447(3)
N1 O5 1.210(3)
N1 O6 1.218(3)
C2 C3 1.394(3)
C5 C6 1.364(3)
C5 C4 1.413(3)
C7 H7A 1.00(4)
C7 H7B 0.94(3)
C7 H7C 0.96(4)
C3 C4 1.377(3)
C3 H3 0.94(2)
C9 H9A 1.02(4)
C9 H9B 0.96(3)
C9 H9C 1.00(4)
C8 H8A 1.00(5)
C8 H8B 1.01(3)
C8 H8C 1.05(4)
C6 H6 0.95(2)
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
C2 C1 N1 O5 13.3(4) ?
C6 C1 N1 O5 -165.9(3) ?
C2 C1 N1 O6 -168.5(3) ?
C6 C1 N1 O6 12.4(4) ?
C7 O1 C2 C3 4.9(5) ?
C7 O1 C2 C1 -176.6(3) y
C6 C1 C2 O1 -177.4(3) ?
N1 C1 C2 O1 3.5(4) ?
C6 C1 C2 C3 1.2(4) ?
N1 C1 C2 C3 -177.9(3) ?
C9 O4 C5 C6 -4.3(4) ?
C9 O4 C5 C4 176.2(3) y
O1 C2 C3 C4 177.5(3) ?
C1 C2 C3 C4 -1.0(4) ?
C8 O3 C4 C3 -5.0(4) ?
C8 O3 C4 C5 175.3(3) y
C2 C3 C4 O3 -179.3(3) ?
C2 C3 C4 C5 0.5(4) ?
O4 C5 C4 O3 -0.7(4) ?
C6 C5 C4 O3 179.7(3) ?
O4 C5 C4 C3 179.5(3) ?
C6 C5 C4 C3 0.0(4) ?
O4 C5 C6 C1 -179.3(3) ?
C4 C5 C6 C1 0.2(4) ?
C2 C1 C6 C5 -0.8(4) ?
N1 C1 C6 C5 178.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 718425
2 PubChem 822415
