#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:35:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/19/2021934.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_2021934
loop_
_publ_author_name
'Tan, Xue-Jie'
'Liu, Shuai'
'Hei, Xiao-Ming'
'Yang, Feng-Cun'
'He, Peng-Bing'
'Guo, Feng'
'Xing, Dian-Xiang'
_publ_section_title
;
 Structural and theoretical study of four novel norcantharidine
 derivatives: two new cases of conditional isomorphism
;
_journal_coeditor_code           YO3069
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              75
_journal_page_last               86
_journal_paper_doi               10.1107/S2053229619016164
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C14 H10 N2 O5'
_chemical_formula_moiety         'C14 H10 N2 O5'
_chemical_formula_sum            'C14 H10 N2 O5'
_chemical_formula_weight         286.24
_chemical_name_systematic
(3aR,4S,7R,7aS)-2-(4-Nitrophenyl)-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 100.105(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.285(3)
_cell_length_b                   18.418(9)
_cell_length_c                   6.699(3)
_cell_measurement_reflns_used    380
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.45
_cell_volume                     642.0(6)
_computing_cell_refinement
;
SMART (Bruker, 2000)
;
_computing_data_collection
;
SMART (Bruker, 2000)
;
_computing_data_reduction
;
SAINT (Bruker, 2000)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2000), PLATON (Spek, 2009), WinGX2014
(Farrugia, 2012),
DIAMOND (Brandenburg & Putz, 1999) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.13
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.212
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2000)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.358
_refine_ls_abs_structure_details
;
Flack x determined using 381 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0666
_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)+(0.1020P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                1541
_reflns_number_total             2191
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yo3069sup1.cif
_cod_data_source_block           DNCA-NA
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2021934
_cod_database_fobs_code          2021934
_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.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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_occupancy
C C1 0.3179(11) 0.3910(3) 0.0715(10) 0.0508(14) Uani d 1
C C2 0.5903(10) 0.4140(3) 0.0360(8) 0.0409(12) Uani d 1
C C3 0.5217(9) 0.4617(3) -0.1547(7) 0.0408(11) Uani d 1
C C4 0.2286(10) 0.4538(3) -0.2019(8) 0.0479(12) Uani d 1
C C5 0.1666(11) 0.3760(3) -0.2614(10) 0.0643(17) Uani d 1
H H5 0.102698 0.358733 -0.390942 0.08(2) Uiso calc 1
C C6 0.2202(11) 0.3377(3) -0.0959(9) 0.0568(16) Uani d 1
H H6 0.202080 0.287734 -0.083342 0.059(17) Uiso calc 1
C C7 0.7219(9) 0.4641(3) 0.1978(8) 0.0467(12) Uani d 1
C C8 0.6040(9) 0.5366(3) -0.0860(7) 0.0416(11) Uani d 1
C C9 0.8574(9) 0.5930(3) 0.2274(7) 0.0422(12) Uani d 1
C C10 0.7976(11) 0.6095(3) 0.4159(8) 0.0517(14) Uani d 1
C C11 0.9424(13) 0.6614(3) 0.5333(10) 0.0584(16) Uani d 1
C C12 1.1333(12) 0.6955(3) 0.4603(10) 0.0571(15) Uani d 1
C C13 1.1917(12) 0.6809(3) 0.2715(11) 0.0584(15) Uani d 1
C C14 1.0504(11) 0.6282(3) 0.1545(9) 0.0514(13) Uani d 1
N N1 0.7245(8) 0.5338(2) 0.1175(6) 0.0412(9) Uani d 1
N N2 1.2952(15) 0.7485(3) 0.5922(13) 0.087(2) Uani d 1
O O1 0.1724(7) 0.4551(2) 0.0023(6) 0.0528(10) Uani d 1
O O2 0.8097(9) 0.4487(3) 0.3704(6) 0.0730(14) Uani d 1
O O3 0.5735(9) 0.5923(2) -0.1820(5) 0.0628(11) Uani d 1
O O4 1.2474(15) 0.7575(3) 0.7650(11) 0.119(3) Uani d 1
O O5 1.4660(14) 0.7777(4) 0.5304(12) 0.120(2) Uani d 1
H H1 0.292(11) 0.382(3) 0.208(10) 0.053(16) Uiso d 1
H H2 0.684(10) 0.374(3) 0.030(8) 0.043(15) Uiso d 1
H H3 0.600(9) 0.450(3) -0.266(7) 0.027(10) Uiso d 1
H H4 0.149(10) 0.496(3) -0.284(7) 0.039(13) Uiso d 1
H H10 0.663(12) 0.585(4) 0.462(9) 0.055(16) Uiso d 1
H H11 0.886(12) 0.670(3) 0.644(10) 0.054(17) Uiso d 1
H H13 1.323(13) 0.701(4) 0.226(9) 0.061(18) Uiso d 1
H H14 1.108(12) 0.620(3) 0.029(9) 0.057(17) Uiso d 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
O1 C1 C6 101.6(4)
O1 C1 C2 100.6(4)
C6 C1 C2 105.5(5)
O1 C1 H1 107(4)
C6 C1 H1 120(3)
C2 C1 H1 119(3)
C7 C2 C3 105.1(4)
C7 C2 C1 112.4(5)
C3 C2 C1 101.1(4)
C7 C2 H2 110(3)
C3 C2 H2 119(3)
C1 C2 H2 109(3)
C8 C3 C4 112.4(4)
C8 C3 C2 104.9(4)
C4 C3 C2 101.5(4)
C8 C3 H3 108(3)
C4 C3 H3 113(3)
C2 C3 H3 117(3)
O1 C4 C5 101.2(5)
O1 C4 C3 99.8(4)
C5 C4 C3 108.0(5)
O1 C4 H4 112(3)
C5 C4 H4 123(3)
C3 C4 H4 111(3)
C6 C5 C4 106.6(5)
C6 C5 H5 126.7
C4 C5 H5 126.7
C5 C6 C1 105.9(5)
C5 C6 H6 127.0
C1 C6 H6 127.0
O2 C7 N1 124.1(5)
O2 C7 C2 127.1(5)
N1 C7 C2 108.8(4)
O3 C8 N1 123.1(5)
O3 C8 C3 128.0(4)
N1 C8 C3 108.9(4)
C14 C9 C10 121.6(5)
C14 C9 N1 120.5(5)
C10 C9 N1 117.8(5)
C11 C10 C9 118.5(6)
C11 C10 H10 121(4)
C9 C10 H10 120(4)
C12 C11 C10 119.4(6)
C12 C11 H11 128(4)
C10 C11 H11 112(4)
C11 C12 C13 122.8(6)
C11 C12 N2 118.7(6)
C13 C12 N2 118.4(7)
C12 C13 C14 118.2(6)
C12 C13 H13 123(4)
C14 C13 H13 118(4)
C9 C14 C13 119.5(6)
C9 C14 H14 127(4)
C13 C14 H14 113(4)
C7 N1 C8 112.1(4)
C7 N1 C9 122.8(4)
C8 N1 C9 124.8(4)
O5 N2 O4 123.9(7)
O5 N2 C12 119.0(8)
O4 N2 C12 117.0(8)
C1 O1 C4 96.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.441(7)
C1 C6 1.512(8)
C1 C2 1.558(8)
C1 H1 0.96(6)
C2 C7 1.499(7)
C2 C3 1.540(7)
C2 H2 0.89(6)
C3 C8 1.495(8)
C3 C4 1.532(7)
C3 H3 0.94(5)
C4 O1 1.450(7)
C4 C5 1.508(9)
C4 H4 1.00(5)
C5 C6 1.303(9)
C5 H5 0.9300
C6 H6 0.9300
C7 O2 1.202(6)
C7 N1 1.393(7)
C8 O3 1.205(6)
C8 N1 1.401(6)
C9 C14 1.369(8)
C9 C10 1.388(7)
C9 N1 1.430(6)
C10 C11 1.380(9)
C10 H10 0.94(7)
C11 C12 1.351(10)
C11 H11 0.86(7)
C12 C13 1.380(9)
C12 N2 1.484(8)
C13 C14 1.381(9)
C13 H13 0.89(7)
C14 H14 0.95(6)
N2 O5 1.186(9)
N2 O4 1.238(10)
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
C2 H2 O4 2_746 0.89(6) 2.55(6) 3.228(8) 134(4)
C10 H10 O3 1_556 0.94(7) 2.51(6) 3.143(8) 124(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11219886
