#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/66/2226667.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_2226667
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Khan, Salman A.'
'Tan, Kong Wai'
'Ng, Seik Weng'
_publ_section_title
;
 4-Nitroaniline--2,4,6-trimethoxybenzaldehyde (1/1)
;
_journal_coeditor_code           SI2271
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1765
_journal_paper_doi               10.1107/S1600536810023664
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H6 N2 O2, C10 H12 O4'
_chemical_formula_moiety         'C6 H6 N2 O2, C10 H12 O4'
_chemical_formula_sum            'C16 H18 N2 O6'
_chemical_formula_weight         334.32
_chemical_name_systematic
;
4-Nitroaniline--2,4,6-trimethoxybenzaldehyde (1/1)
;
_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                90.00
_cell_angle_beta                 93.237(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4409(11)
_cell_length_b                   30.022(5)
_cell_length_c                   6.9400(11)
_cell_measurement_reflns_used    1019
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      2.7
_cell_volume                     1547.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8127
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.411
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0537P)²+0.1410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                1834
_reflns_number_total             2722
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2271.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226667
_cod_database_fobs_code          2226667
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.7019(2) 0.57392(6) 0.7861(3) 0.0238(5) Uani d . 1 . .
O O2 0.7670(2) 0.61120(6) 0.4418(2) 0.0182(4) Uani d . 1 . .
O O3 1.3371(2) 0.57367(6) 0.1850(2) 0.0203(4) Uani d . 1 . .
O O4 1.1646(2) 0.51253(6) 0.7725(2) 0.0176(4) Uani d . 1 . .
O O5 0.0363(2) 0.80574(6) 0.5273(3) 0.0266(5) Uani d . 1 . .
O O6 -0.0908(2) 0.74324(7) 0.4450(3) 0.0291(5) Uani d . 1 . .
N N1 0.6593(3) 0.67379(7) 0.7727(3) 0.0233(5) Uani d . 1 . .
H H11 0.7505 0.6884 0.8209 0.028 Uiso calc R 1 . .
H H12 0.6631 0.6452 0.7670 0.028 Uiso calc R 1 . .
N N2 0.0398(3) 0.76456(7) 0.5159(3) 0.0193(5) Uani d . 1 . .
C C1 0.8433(3) 0.55435(8) 0.7589(4) 0.0177(6) Uani d . 1 . .
H H1 0.8764 0.5314 0.8482 0.021 Uiso calc R 1 . .
C C2 0.9658(3) 0.56212(8) 0.6066(3) 0.0152(6) Uani d . 1 . .
C C3 0.9285(3) 0.59010(8) 0.4462(4) 0.0154(6) Uani d . 1 . .
C C4 1.0482(3) 0.59515(8) 0.3011(4) 0.0155(6) Uani d . 1 . .
H H4 1.0203 0.6140 0.1936 0.019 Uiso calc R 1 . .
C C5 1.2098(3) 0.57189(8) 0.3175(4) 0.0157(6) Uani d . 1 . .
C C6 1.2542(3) 0.54410(8) 0.4744(4) 0.0170(6) Uani d . 1 . .
H H6 1.3662 0.5289 0.4834 0.020 Uiso calc R 1 . .
C C7 1.1335(3) 0.53914(8) 0.6155(3) 0.0144(6) Uani d . 1 . .
C C8 0.7184(3) 0.63908(9) 0.2781(4) 0.0216(6) Uani d . 1 . .
H H8A 0.5983 0.6516 0.2923 0.032 Uiso calc R 1 . .
H H8B 0.7179 0.6213 0.1597 0.032 Uiso calc R 1 . .
H H8C 0.8061 0.6633 0.2709 0.032 Uiso calc R 1 . .
C C9 1.3034(3) 0.60080(8) 0.0177(4) 0.0198(6) Uani d . 1 . .
H H9A 1.4039 0.5980 -0.0669 0.030 Uiso calc R 1 . .
H H9B 1.2913 0.6320 0.0570 0.030 Uiso calc R 1 . .
H H9C 1.1920 0.5910 -0.0516 0.030 Uiso calc R 1 . .
C C10 1.3340(3) 0.48903(9) 0.7879(4) 0.0193(6) Uani d . 1 . .
H H10A 1.3403 0.4709 0.9054 0.029 Uiso calc R 1 . .
H H10B 1.4332 0.5106 0.7934 0.029 Uiso calc R 1 . .
H H10C 1.3436 0.4697 0.6751 0.029 Uiso calc R 1 . .
C C11 0.5099(3) 0.69579(9) 0.7057(3) 0.0168(6) Uani d . 1 . .
C C12 0.3577(3) 0.67245(9) 0.6292(4) 0.0189(6) Uani d . 1 . .
H H12A 0.3622 0.6409 0.6183 0.023 Uiso calc R 1 . .
C C13 0.2034(3) 0.69466(9) 0.5705(4) 0.0186(6) Uani d . 1 . .
H H13 0.1006 0.6786 0.5216 0.022 Uiso calc R 1 . .
C C14 0.1986(3) 0.74094(8) 0.5832(4) 0.0165(6) Uani d . 1 . .
C C15 0.3483(3) 0.76498(8) 0.6542(3) 0.0162(6) Uani d . 1 . .
H H15 0.3440 0.7966 0.6610 0.019 Uiso calc R 1 . .
C C16 0.5015(3) 0.74254(9) 0.7139(4) 0.0176(6) Uani d . 1 . .
H H16 0.6040 0.7588 0.7617 0.021 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O2 C8 . . 118.10(19) ?
C5 O3 C9 . . 118.39(19) ?
C7 O4 C10 . . 117.03(19) ?
C11 N1 H11 . . 120.0 ?
C11 N1 H12 . . 120.0 ?
H11 N1 H12 . . 120.0 ?
O5 N2 O6 . . 121.4(2) ?
O5 N2 C14 . . 119.5(2) ?
O6 N2 C14 . . 119.1(2) ?
O1 C1 C2 . . 127.8(2) ?
O1 C1 H1 . . 116.1 ?
C2 C1 H1 . . 116.1 ?
C3 C2 C7 . . 117.2(2) ?
C3 C2 C1 . . 124.5(2) ?
C7 C2 C1 . . 118.3(2) ?
O2 C3 C4 . . 122.4(2) ?
O2 C3 C2 . . 115.5(2) ?
C4 C3 C2 . . 122.1(2) ?
C3 C4 C5 . . 118.2(2) ?
C3 C4 H4 . . 120.9 ?
C5 C4 H4 . . 120.9 ?
O3 C5 C4 . . 123.9(2) ?
O3 C5 C6 . . 114.1(2) ?
C4 C5 C6 . . 122.0(2) ?
C7 C6 C5 . . 119.0(2) ?
C7 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
O4 C7 C6 . . 123.1(2) ?
O4 C7 C2 . . 115.4(2) ?
C6 C7 C2 . . 121.5(2) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O3 C9 H9A . . 109.5 ?
O3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O4 C10 H10A . . 109.5 ?
O4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N1 C11 C16 . . 120.7(2) ?
N1 C11 C12 . . 120.9(2) ?
C16 C11 C12 . . 118.3(2) ?
C13 C12 C11 . . 120.8(2) ?
C13 C12 H12A . . 119.6 ?
C11 C12 H12A . . 119.6 ?
C12 C13 C14 . . 119.4(2) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C15 C14 C13 . . 121.1(2) ?
C15 C14 N2 . . 119.1(2) ?
C13 C14 N2 . . 119.7(2) ?
C16 C15 C14 . . 119.2(2) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C11 . . 121.2(2) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.229(3) ?
O2 C3 . 1.357(3) ?
O2 C8 . 1.441(3) ?
O3 C5 . 1.358(3) ?
O3 C9 . 1.428(3) ?
O4 C7 . 1.360(3) ?
O4 C10 . 1.444(3) ?
O5 N2 . 1.239(3) ?
O6 N2 . 1.242(3) ?
N1 C11 . 1.352(3) ?
N1 H11 . 0.8600 ?
N1 H12 . 0.8600 ?
N2 C14 . 1.434(3) ?
C1 C2 . 1.454(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.409(3) ?
C2 C7 . 1.424(3) ?
C3 C4 . 1.390(3) ?
C4 C5 . 1.389(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.397(3) ?
C6 C7 . 1.374(3) ?
C6 H6 . 0.9500 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C16 . 1.406(4) ?
C11 C12 . 1.410(3) ?
C12 C13 . 1.370(3) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.393(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.394(3) ?
C15 C16 . 1.368(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
N1 H12 O1 . 0.86 2.16 3.016(3) 172 yes
N1 H11 O5 4_676 0.86 2.50 3.288(3) 152 yes
N1 H11 O6 4_676 0.86 2.50 3.293(3) 154 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -9.3(4) ?
O1 C1 C2 C7 . . . . 172.5(2) ?
C8 O2 C3 C4 . . . . 1.2(3) ?
C8 O2 C3 C2 . . . . -177.9(2) ?
C7 C2 C3 O2 . . . . 179.5(2) ?
C1 C2 C3 O2 . . . . 1.3(4) ?
C7 C2 C3 C4 . . . . 0.5(3) ?
C1 C2 C3 C4 . . . . -177.7(2) ?
O2 C3 C4 C5 . . . . -179.5(2) ?
C2 C3 C4 C5 . . . . -0.5(4) ?
C9 O3 C5 C4 . . . . -0.4(3) ?
C9 O3 C5 C6 . . . . 179.3(2) ?
C3 C4 C5 O3 . . . . 179.4(2) ?
C3 C4 C5 C6 . . . . -0.2(4) ?
O3 C5 C6 C7 . . . . -178.8(2) ?
C4 C5 C6 C7 . . . . 0.9(4) ?
C10 O4 C7 C6 . . . . 0.3(3) ?
C10 O4 C7 C2 . . . . -179.4(2) ?
C5 C6 C7 O4 . . . . 179.5(2) ?
C5 C6 C7 C2 . . . . -0.9(4) ?
C3 C2 C7 O4 . . . . 179.9(2) ?
C1 C2 C7 O4 . . . . -1.8(3) ?
C3 C2 C7 C6 . . . . 0.2(3) ?
C1 C2 C7 C6 . . . . 178.6(2) ?
N1 C11 C12 C13 . . . . 176.7(2) ?
C16 C11 C12 C13 . . . . -2.2(4) ?
C11 C12 C13 C14 . . . . 1.3(4) ?
C12 C13 C14 C15 . . . . 0.2(4) ?
C12 C13 C14 N2 . . . . 177.8(2) ?
O5 N2 C14 C15 . . . . -2.2(3) ?
O6 N2 C14 C15 . . . . 176.9(2) ?
O5 N2 C14 C13 . . . . -179.9(2) ?
O6 N2 C14 C13 . . . . -0.8(3) ?
C13 C14 C15 C16 . . . . -0.6(4) ?
N2 C14 C15 C16 . . . . -178.3(2) ?
C14 C15 C16 C11 . . . . -0.3(4) ?
N1 C11 C16 C15 . . . . -177.2(2) ?
C12 C11 C16 C15 . . . . 1.7(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079189
