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#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520427.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_1520427
loop_
_publ_author_name
'Holliman, Peter J.'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C12H8N2O4
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              650
_journal_year                    2009
_chemical_formula_sum            'C12 H8 N2 O4'
_chemical_formula_weight         244.20
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                108.0280(10)
_cell_angle_beta                 96.346(2)
_cell_angle_gamma                107.648(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7644(2)
_cell_length_b                   8.7396(3)
_cell_length_c                   9.6184(3)
_cell_measurement_reflns_used    7330
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     576.19(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14073
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0439
_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)+(0.0594P)²+0.2416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                2173
_reflns_number_total             2622
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-650.cif
_cod_data_source_block           2009src0189
_cod_depositor_comments
;
Citation :
Holliman, Peter J. and Callear, Samantha K. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/650)

More at:
http://ecrystals.chem.soton.ac.uk/650/
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1520427
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1191(2) -0.33899(19) -0.49227(17) 0.0279(3) Uani 1 1 d . . .
H1A H -0.2405 -0.3298 -0.5170 0.042 Uiso 1 1 calc R . .
H1B H -0.1268 -0.4135 -0.4334 0.042 Uiso 1 1 calc R . .
H1C H -0.0819 -0.3884 -0.5850 0.042 Uiso 1 1 calc R . .
C2 C 0.02044(19) -0.16481(18) -0.40326(15) 0.0205(3) Uani 1 1 d . . .
C4 C 0.10772(19) 0.05260(17) -0.16034(15) 0.0186(3) Uani 1 1 d . . .
C5 C 0.08269(19) 0.19507(18) -0.18193(16) 0.0208(3) Uani 1 1 d . . .
H5 H -0.0010 0.1806 -0.2689 0.025 Uiso 1 1 calc R . .
C6 C 0.18013(19) 0.35848(18) -0.07625(16) 0.0208(3) Uani 1 1 d . . .
H6 H 0.1653 0.4566 -0.0912 0.025 Uiso 1 1 calc R . .
C7 C 0.29967(18) 0.37775(17) 0.05177(15) 0.0183(3) Uani 1 1 d . . .
C8 C 0.32527(18) 0.23652(18) 0.07538(15) 0.0186(3) Uani 1 1 d . . .
C9 C 0.22914(18) 0.07065(17) -0.03398(15) 0.0183(3) Uani 1 1 d . . .
C10 C 0.2554(2) -0.07770(18) -0.01356(16) 0.0216(3) Uani 1 1 d . . .
C12 C 0.4443(2) 0.25919(19) 0.21141(17) 0.0238(3) Uani 1 1 d . . .
C15 C 0.30751(19) 0.62712(17) 0.24287(15) 0.0187(3) Uani 1 1 d . . .
C16 C 0.4329(2) 0.80338(19) 0.34257(16) 0.0246(3) Uani 1 1 d . . .
H16A H 0.3644 0.8824 0.3548 0.037 Uiso 1 1 calc R . .
H16B H 0.5375 0.8422 0.2978 0.037 Uiso 1 1 calc R . .
H16C H 0.4796 0.8017 0.4408 0.037 Uiso 1 1 calc R . .
N11 N 0.27841(19) -0.19418(17) 0.00492(16) 0.0295(3) Uani 1 1 d . . .
N13 N 0.5361(2) 0.2757(2) 0.32100(16) 0.0371(4) Uani 1 1 d . . .
O2 O 0.13563(15) -0.07479(14) -0.44476(12) 0.0275(3) Uani 1 1 d . . .
O3 O -0.00044(14) -0.11374(13) -0.25656(11) 0.0225(2) Uani 1 1 d . . .
O14 O 0.40399(13) 0.54028(12) 0.15707(11) 0.0211(2) Uani 1 1 d . . .
O15 O 0.14545(14) 0.56060(13) 0.23457(12) 0.0247(3) Uani 1 1 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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O2 C2 O3 121.91(13) . .
O2 C2 C1 128.14(13) . .
O3 C2 C1 109.95(12) . .
C9 C4 C5 121.10(13) . .
C9 C4 O3 117.43(12) . .
C5 C4 O3 121.19(12) . .
C6 C5 C4 119.84(13) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C5 C6 C7 119.54(13) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
C8 C7 O14 117.83(12) . .
C8 C7 C6 121.29(13) . .
O14 C7 C6 120.82(12) . .
C7 C8 C9 119.08(12) . .
C7 C8 C12 120.21(13) . .
C9 C8 C12 120.69(12) . .
C4 C9 C8 119.13(12) . .
C4 C9 C10 120.62(12) . .
C8 C9 C10 120.25(12) . .
N11 C10 C9 178.87(16) . .
N13 C12 C8 178.53(16) . .
O15 C15 O14 121.64(12) . .
O15 C15 C16 127.58(13) . .
O14 C15 C16 110.76(11) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C2 O3 C4 117.84(10) . .
C15 O14 C7 116.35(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.487(2) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 O2 1.1937(18) .
C2 O3 1.3861(17) .
C4 C9 1.3888(19) .
C4 C5 1.389(2) .
C4 O3 1.3894(16) .
C5 C6 1.386(2) .
C5 H5 0.9500 .
C6 C7 1.389(2) .
C6 H6 0.9500 .
C7 C8 1.388(2) .
C7 O14 1.3893(16) .
C8 C9 1.4112(19) .
C8 C12 1.438(2) .
C9 C10 1.439(2) .
C10 N11 1.147(2) .
C12 N13 1.148(2) .
C15 O15 1.1972(17) .
C15 O14 1.3827(17) .
C15 C16 1.4868(19) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 134319
