#------------------------------------------------------------------------------
#$Date: 2022-03-10 10:33:12 +0200 (Thu, 10 Mar 2022) $
#$Revision: 273589 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104712.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_8104712
loop_
_publ_author_name
'Hao, Chen-Hong'
'Meng, Jiao'
'Tian, Jing'
'Luo, Xiao-Fang'
'Wang, Zong-Cheng'
_publ_section_title
;
 Synthesis and crystal structure of 4-(2,4-dinitrophenoxy)benzaldehyde,
 C13H8N2O6
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              789
_journal_page_last               790
_journal_paper_doi               10.1515/ncrs-2021-0099
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C13 H8 N2 O6'
_chemical_formula_sum            'C13 H8 N2 O6'
_chemical_formula_weight         288.21
_chemical_name_systematic        ;4-(2,4-dinitrophenoxy)benzaldehyde;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                100.988(3)
_cell_angle_beta                 95.557(3)
_cell_angle_gamma                107.424(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9561(5)
_cell_length_b                   7.3040(5)
_cell_length_c                   13.2883(8)
_cell_measurement_reflns_used    2809
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      3.00
_cell_volume                     623.76(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_min         3.004
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0640 before and 0.0582 after correction.
The Ratio of minimum to maximum transmission is 0.3986.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0438P)²+0.0861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1876
_reflns_number_total             2562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0099_suppl.cif
_cod_data_source_block           mo_1214_2_0m
_cod_database_code               8104712
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_exptl_absorpt_special_details   block
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2467(2) 1.08268(19) -0.11791(11) 0.0519(3) Uani 1 1 d . . . . .
O2 O 0.84046(19) 1.02839(17) 0.59963(10) 0.0469(3) Uani 1 1 d . . . . .
O3 O 0.6287(2) 0.81285(18) 0.66314(10) 0.0479(3) Uani 1 1 d . . . . .
O4 O 0.02244(19) 0.32438(17) 0.42557(11) 0.0481(3) Uani 1 1 d . . . A 2
O5 O 0.22268(19) 0.51835(17) 0.19702(9) 0.0452(3) Uani 1 1 d . . . . .
O6 O -0.0833(2) 0.4776(2) 0.31894(11) 0.0549(4) Uani 1 1 d . . . . .
N1 N 0.0516(2) 0.4485(2) 0.37286(12) 0.0421(4) Uani 1 1 d . . . . .
N2 N 0.6880(2) 0.8835(2) 0.59039(12) 0.0407(3) Uani 1 1 d . . . B 1
C1 C 0.5691(3) 0.7892(2) 0.48646(13) 0.0371(4) Uani 1 1 d . . . . .
C2 C 0.3766(3) 0.6564(2) 0.47831(13) 0.0371(4) Uani 1 1 d . . . . .
H2 H 0.324662 0.621622 0.538031 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2521(2) 0.8163(2) -0.04020(13) 0.0395(4) Uani 1 1 d . . . . .
C4 C 0.2627(2) 0.5762(2) 0.38073(14) 0.0374(4) Uani 1 1 d . . . . .
C5 C 0.2698(3) 0.5324(2) 0.02341(14) 0.0408(4) Uani 1 1 d . . . . .
H5 H 0.287257 0.406349 0.012922 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3398(3) 0.6182(2) 0.29140(13) 0.0398(4) Uani 1 1 d . . . . .
C7 C 0.2349(3) 0.6219(2) 0.11781(13) 0.0393(4) Uani 1 1 d . . . . .
C8 C 0.2109(3) 0.8994(2) 0.05570(14) 0.0410(4) Uani 1 1 d . . . . .
H8 H 0.189513 1.023713 0.066190 0.049 Uiso 1 1 calc R U . . .
C9 C 0.6511(3) 0.8368(2) 0.40003(14) 0.0409(4) Uani 1 1 d . . . . .
H9 H 0.784099 0.929183 0.407888 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2012(3) 0.8019(2) 0.13489(14) 0.0420(4) Uani 1 1 d . . . . .
H10 H 0.172044 0.856929 0.200038 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2787(3) 0.6324(3) -0.05553(14) 0.0418(4) Uani 1 1 d . . . . .
H11 H 0.303436 0.574478 -0.121222 0.050 Uiso 1 1 calc R U . . .
C12 C 0.5370(3) 0.7480(2) 0.30267(14) 0.0426(4) Uani 1 1 d . . . . .
H12 H 0.593546 0.775753 0.242817 0.051 Uiso 1 1 calc R U . . .
C13 C 0.2704(3) 0.9237(3) -0.12384(14) 0.0446(4) Uani 1 1 d . . . . .
H13 H 0.303247 0.863968 -0.186923 0.054 Uiso 1 1 calc R U . . .
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
C6 O5 C7 116.79(13) . .
O4 N1 C4 117.00(15) . .
O6 N1 O4 124.45(15) . .
O6 N1 C4 118.47(15) . .
O2 N2 C1 118.12(14) . .
O3 N2 O2 124.10(15) . .
O3 N2 C1 117.78(14) . .
C2 C1 N2 118.15(15) . .
C2 C1 C9 122.21(16) . .
C9 C1 N2 119.64(15) . .
C1 C2 H2 121.2 . .
C4 C2 C1 117.58(16) . .
C4 C2 H2 121.2 . .
C8 C3 C13 120.42(16) . .
C11 C3 C8 119.44(17) . .
C11 C3 C13 120.13(16) . .
C2 C4 N1 117.58(15) . .
C2 C4 C6 122.12(16) . .
C6 C4 N1 120.26(16) . .
C7 C5 H5 121.1 . .
C7 C5 C11 117.73(16) . .
C11 C5 H5 121.1 . .
O5 C6 C4 118.11(15) . .
O5 C6 C12 123.23(16) . .
C12 C6 C4 118.48(16) . .
C5 C7 O5 117.48(15) . .
C5 C7 C10 122.80(17) . .
C10 C7 O5 119.63(15) . .
C3 C8 H8 119.9 . .
C10 C8 C3 120.24(16) . .
C10 C8 H8 119.9 . .
C1 C9 H9 120.5 . .
C12 C9 C1 119.05(16) . .
C12 C9 H9 120.5 . .
C7 C10 H10 120.7 . .
C8 C10 C7 118.67(16) . .
C8 C10 H10 120.7 . .
C3 C11 H11 119.5 . .
C5 C11 C3 121.05(16) . .
C5 C11 H11 119.5 . .
C6 C12 H12 119.8 . .
C9 C12 C6 120.45(17) . .
C9 C12 H12 119.8 . .
O1 C13 C3 124.62(17) . .
O1 C13 H13 117.7 . .
C3 C13 H13 117.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.210(2) .
O2 N2 1.2299(18) .
O3 N2 1.2292(19) .
O4 N1 1.2304(19) .
O5 C6 1.366(2) .
O5 C7 1.403(2) .
O6 N1 1.219(2) .
N1 C4 1.466(2) .
N2 C1 1.463(2) .
C1 C2 1.378(2) .
C1 C9 1.388(2) .
C2 H2 0.9500 .
C2 C4 1.373(2) .
C3 C8 1.398(2) .
C3 C11 1.390(2) .
C3 C13 1.472(2) .
C4 C6 1.398(2) .
C5 H5 0.9500 .
C5 C7 1.379(2) .
C5 C11 1.384(3) .
C6 C12 1.389(2) .
C7 C10 1.384(2) .
C8 H8 0.9500 .
C8 C10 1.375(2) .
C9 H9 0.9500 .
C9 C12 1.377(2) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 H13 0.9500 .
