#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/47/2204795.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_2204795
loop_
_publ_author_name
'Liu, Xin-Gang'
'Feng, Ya-Qing'
'Wu, Peng'
'Chen, Xue'
'Li, Fei'
_publ_section_title
;
 4-(1,3-Dioxoisoindolin-2-yl)benzaldehyde
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2293
_journal_page_last               o2294
_journal_paper_doi               10.1107/S1600536804028272
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H9 N O3'
_chemical_formula_moiety         'C15 H9 N O3'
_chemical_formula_sum            'C15 H9 N O3'
_chemical_formula_weight         251.23
_chemical_melting_point          .2E-198
_chemical_name_systematic
;
4-(1,3-dioxoisoindolin-2-yl)benzaldehyde
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.646(3)
_cell_length_b                   11.070(4)
_cell_length_c                   13.815(4)
_cell_measurement_reflns_used    1004
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.13
_cell_measurement_theta_min      2.36
_cell_volume                     1169.3(7)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6256
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1227
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0446P)²+0.1003P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                947
_reflns_number_total             1227
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6020.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     'p 2c -2n'
_cod_database_code               2204795
_cod_database_fobs_code          2204795
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
O1 0.1196(3) 1.06929(19) 0.26993(16) 0.0580(6) Uani d . 1 O
O2 0.3641(3) 0.69214(19) 0.27035(16) 0.0571(6) Uani d . 1 O
N1 0.2437(3) 0.8811(2) 0.29607(17) 0.0383(6) Uani d . 1 N
C1 0.1770(4) 0.9753(3) 0.2392(2) 0.0409(7) Uani d . 1 C
C2 0.1926(4) 0.9325(3) 0.1376(2) 0.0397(7) Uani d . 1 C
C3 0.1478(4) 0.9891(3) 0.0519(3) 0.0495(8) Uani d . 1 C
H3 0.0946 1.0646 0.0516 0.059 Uiso calc R 1 H
C4 0.1856(4) 0.9286(4) -0.0339(2) 0.0566(10) Uani d . 1 C
H4 0.1584 0.9647 -0.0928 0.068 Uiso calc R 1 H
C5 0.2622(5) 0.8166(4) -0.0331(2) 0.0569(9) Uani d . 1 C
H5 0.2855 0.7778 -0.0914 0.068 Uiso calc R 1 H
C6 0.3059(4) 0.7599(3) 0.0538(3) 0.0498(7) Uani d . 1 C
H6 0.3582 0.6840 0.0547 0.060 Uiso calc R 1 H
C7 0.2685(3) 0.8202(3) 0.1378(2) 0.0376(7) Uani d . 1 C
C8 0.3002(4) 0.7840(3) 0.2400(2) 0.0391(7) Uani d . 1 C
C9 0.2575(4) 0.8826(3) 0.3991(2) 0.0360(7) Uani d . 1 C
C10 0.1847(4) 0.7895(3) 0.4527(2) 0.0438(8) Uani d . 1 C
H10 0.1232 0.7277 0.4224 0.053 Uiso calc R 1 H
C11 0.2052(4) 0.7904(3) 0.5522(2) 0.0471(7) Uani d . 1 C
H11 0.1560 0.7288 0.5890 0.056 Uiso calc R 1 H
C12 0.2976(4) 0.8812(3) 0.5975(2) 0.0426(8) Uani d . 1 C
C13 0.3681(4) 0.9737(3) 0.5428(2) 0.0472(8) Uani d . 1 C
H13 0.4290 1.0358 0.5732 0.057 Uiso calc R 1 H
C14 0.3487(4) 0.9746(3) 0.4437(2) 0.0447(8) Uani d . 1 C
H14 0.3967 1.0368 0.4071 0.054 Uiso calc R 1 H
C15 0.3234(5) 0.8756(4) 0.7035(3) 0.0663(11) Uani d . 1 C
H15 0.2602 0.8184 0.7382 0.080 Uiso calc R 1 H
O3 0.4206(4) 0.9404(3) 0.74705(19) 0.1001(11) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C8 N1 C1 112.1(2)
C8 N1 C9 122.7(3)
C1 N1 C9 125.2(3)
O1 C1 N1 125.3(3)
O1 C1 C2 129.5(3)
N1 C1 C2 105.2(2)
C7 C2 C3 121.2(3)
C7 C2 C1 108.7(3)
C3 C2 C1 130.1(3)
C2 C3 C4 117.4(3)
C2 C3 H3 121.3
C4 C3 H3 121.3
C5 C4 C3 121.1(3)
C5 C4 H4 119.4
C3 C4 H4 119.4
C4 C5 C6 121.0(3)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C5 117.4(3)
C7 C6 H6 121.3
C5 C6 H6 121.3
C6 C7 C2 121.9(3)
C6 C7 C8 129.7(3)
C2 C7 C8 108.4(3)
O2 C8 N1 125.7(3)
O2 C8 C7 128.7(3)
N1 C8 C7 105.6(2)
C14 C9 C10 120.9(3)
C14 C9 N1 119.4(3)
C10 C9 N1 119.6(3)
C11 C10 C9 118.7(3)
C11 C10 H10 120.6
C9 C10 H10 120.6
C12 C11 C10 120.9(3)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 119.5(3)
C11 C12 C15 119.1(3)
C13 C12 C15 121.4(3)
C14 C13 C12 120.4(3)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C9 119.5(3)
C13 C14 H14 120.2
C9 C14 H14 120.2
O3 C15 C12 123.8(4)
O3 C15 H15 118.1
C12 C15 H15 118.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.206(3)
O2 C8 1.203(3)
N1 C8 1.394(4)
N1 C1 1.401(4)
N1 C9 1.428(3)
C1 C2 1.487(5)
C2 C7 1.372(4)
C2 C3 1.382(5)
C3 C4 1.392(5)
C3 H3 0.9300
C4 C5 1.371(5)
C4 H4 0.9300
C5 C6 1.396(5)
C5 H5 0.9300
C6 C7 1.369(4)
C6 H6 0.9300
C7 C8 1.487(4)
C9 C14 1.379(4)
C9 C10 1.385(4)
C10 C11 1.383(4)
C10 H10 0.9300
C11 C12 1.379(4)
C11 H11 0.9300
C12 C13 1.381(4)
C12 C15 1.479(4)
C13 C14 1.378(5)
C13 H13 0.9300
C14 H14 0.9300
C15 O3 1.195(4)
C15 H15 0.9300
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
C8 N1 C1 O1 179.9(3)
C9 N1 C1 O1 -1.4(5)
C8 N1 C1 C2 0.3(3)
C9 N1 C1 C2 179.0(2)
O1 C1 C2 C7 179.1(3)
N1 C1 C2 C7 -1.3(3)
O1 C1 C2 C3 0.9(5)
N1 C1 C2 C3 -179.6(3)
C7 C2 C3 C4 -1.1(4)
C1 C2 C3 C4 176.9(3)
C2 C3 C4 C5 0.8(5)
C3 C4 C5 C6 -0.4(5)
C4 C5 C6 C7 0.2(5)
C5 C6 C7 C2 -0.5(4)
C5 C6 C7 C8 -179.5(3)
C3 C2 C7 C6 1.0(4)
C1 C2 C7 C6 -177.4(3)
C3 C2 C7 C8 -179.8(3)
C1 C2 C7 C8 1.8(3)
C1 N1 C8 O2 179.3(3)
C9 N1 C8 O2 0.6(5)
C1 N1 C8 C7 0.7(3)
C9 N1 C8 C7 -178.0(2)
C6 C7 C8 O2 -1.0(5)
C2 C7 C8 O2 179.9(3)
C6 C7 C8 N1 177.6(3)
C2 C7 C8 N1 -1.5(3)
C8 N1 C9 C14 122.7(3)
C1 N1 C9 C14 -55.9(4)
C8 N1 C9 C10 -55.0(4)
C1 N1 C9 C10 126.4(3)
C14 C9 C10 C11 -0.1(4)
N1 C9 C10 C11 177.6(3)
C9 C10 C11 C12 -0.6(5)
C10 C11 C12 C13 1.1(5)
C10 C11 C12 C15 -177.2(3)
C11 C12 C13 C14 -1.0(5)
C15 C12 C13 C14 177.3(3)
C12 C13 C14 C9 0.3(5)
C10 C9 C14 C13 0.2(5)
N1 C9 C14 C13 -177.5(3)
C11 C12 C15 O3 169.4(4)
C13 C12 C15 O3 -8.9(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11464425
2 PubChem 12672729
