#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226670.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_2226670
loop_
_publ_author_name
'Fu, Xian-Shu'
'Yu, Xiao-Ping'
'Wang, Wei-Min'
'Lin, Fang'
_publ_section_title
;
 2-(2,2,2-Trifluoroethyl)isoindoline-1,3-dione
;
_journal_coeditor_code           SJ5001
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1745
_journal_paper_doi               10.1107/S1600536810020222
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H6 F3 N O2'
_chemical_formula_moiety         'C10 H6 F3 N O2'
_chemical_formula_sum            'C10 H6 F3 N O2'
_chemical_formula_weight         229.16
_chemical_melting_point          400
_chemical_name_systematic
;
2-(2,2,2-Trifluoroethyl)isoindoline-1,3-dione
;
_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                 95.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0470(10)
_cell_length_b                   9.5370(19)
_cell_length_c                   19.051(4)
_cell_measurement_reflns_used    2545
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.1
_cell_volume                     913.2(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure (Rigaku, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_sigmaI/netI    0.0842
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7732
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.498
_refine_ls_extinction_coef       0.301(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                1009
_reflns_number_total             1608
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226670
_cod_database_fobs_code          2226670
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
F F1 0.3850(3) 0.94405(16) 0.09725(9) 0.0441(5) Uani d . 1 . .
F F2 0.7282(3) 1.04965(15) 0.06326(9) 0.0434(6) Uani d . 1 . .
F F3 0.7509(3) 0.94503(15) 0.16352(8) 0.0424(5) Uani d . 1 . .
O O1 1.0018(3) 0.65493(18) 0.17852(9) 0.0311(5) Uani d . 1 . .
O O2 0.2715(3) 0.63673(19) 0.01945(9) 0.0327(6) Uani d . 1 . .
N N1 0.6488(4) 0.6796(2) 0.09384(11) 0.0258(6) Uani d . 1 . .
C C1 0.7960(5) 0.6112(3) 0.14966(14) 0.0259(7) Uani d . 1 . .
C C2 0.6475(5) 0.4813(3) 0.16200(13) 0.0249(7) Uani d . 1 . .
C C3 0.7001(5) 0.3752(3) 0.21083(14) 0.0288(7) Uani d . 1 . .
H H3 0.8508 0.3792 0.2445 0.035 Uiso calc R 1 . .
C C4 0.5253(5) 0.2632(3) 0.20895(14) 0.0306(7) Uani d . 1 . .
H H4 0.5581 0.1884 0.2416 0.037 Uiso calc R 1 . .
C C5 0.3044(5) 0.2576(3) 0.16073(15) 0.0316(7) Uani d . 1 . .
H H5 0.1870 0.1798 0.1611 0.038 Uiso calc R 1 . .
C C6 0.2508(5) 0.3642(3) 0.11158(14) 0.0289(7) Uani d . 1 . .
H H6 0.0992 0.3609 0.0782 0.035 Uiso calc R 1 . .
C C7 0.4270(5) 0.4746(3) 0.11336(13) 0.0258(7) Uani d . 1 . .
C C8 0.4261(5) 0.6019(3) 0.06811(14) 0.0264(7) Uani d . 1 . .
C C9 0.7342(5) 0.8059(3) 0.06062(14) 0.0296(7) Uani d . 1 . .
H H9A 0.6593 0.8074 0.0108 0.036 Uiso calc R 1 . .
H H9B 0.9306 0.8055 0.0613 0.036 Uiso calc R 1 . .
C C10 0.6488(6) 0.9351(3) 0.09660(15) 0.0326(7) Uani 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'
F F 0.0171 0.0103 '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
C8 N1 C1 . . 111.9(2) ?
C8 N1 C9 . . 123.4(2) ?
C1 N1 C9 . . 124.2(2) ?
O1 C1 N1 . . 124.1(2) ?
O1 C1 C2 . . 130.3(2) ?
N1 C1 C2 . . 105.6(2) ?
C3 C2 C7 . . 120.7(2) ?
C3 C2 C1 . . 130.6(2) ?
C7 C2 C1 . . 108.7(2) ?
C2 C3 C4 . . 117.7(2) ?
C2 C3 H3 . . 121.2 ?
C4 C3 H3 . . 121.2 ?
C5 C4 C3 . . 121.4(2) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 121.1(2) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C7 C6 C5 . . 117.1(2) ?
C7 C6 H6 . . 121.4 ?
C5 C6 H6 . . 121.4 ?
C6 C7 C2 . . 122.0(2) ?
C6 C7 C8 . . 129.9(2) ?
C2 C7 C8 . . 108.1(2) ?
O2 C8 N1 . . 124.6(2) ?
O2 C8 C7 . . 129.7(2) ?
N1 C8 C7 . . 105.6(2) ?
N1 C9 C10 . . 112.2(2) ?
N1 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
N1 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
F3 C10 F1 . . 106.6(2) ?
F3 C10 F2 . . 106.8(2) ?
F1 C10 F2 . . 107.0(2) ?
F3 C10 C9 . . 113.3(2) ?
F1 C10 C9 . . 112.8(2) ?
F2 C10 C9 . . 110.1(2) ?
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
F1 C10 . 1.335(3) ?
F2 C10 . 1.343(3) ?
F3 C10 . 1.334(3) ?
O1 C1 . 1.205(3) ?
O2 C8 . 1.203(3) ?
N1 C8 . 1.398(3) ?
N1 C1 . 1.402(3) ?
N1 C9 . 1.445(3) ?
C1 C2 . 1.478(4) ?
C2 C3 . 1.384(3) ?
C2 C7 . 1.383(3) ?
C3 C4 . 1.384(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.392(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.376(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.489(4) ?
C9 C10 . 1.492(4) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
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
C6 H6 O2 3_565 0.95 2.52 3.462(3) 174 yes
C4 H4 O1 2_745 0.95 2.60 3.229(3) 124 yes
C9 H9B O2 1_655 0.99 2.54 3.311(3) 135 yes
C3 H3 F3 2_745 0.95 2.62 3.556(3) 168 yes
C3 H3 O1 2_745 0.95 2.66 3.247(3) 120 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
C8 N1 C1 O1 . . . . 176.9(2) ?
C9 N1 C1 O1 . . . . 4.5(4) ?
C8 N1 C1 C2 . . . . -2.3(3) ?
C9 N1 C1 C2 . . . . -174.7(2) ?
O1 C1 C2 C3 . . . . 1.4(5) ?
N1 C1 C2 C3 . . . . -179.5(3) ?
O1 C1 C2 C7 . . . . -177.6(3) ?
N1 C1 C2 C7 . . . . 1.6(3) ?
C7 C2 C3 C4 . . . . 0.1(4) ?
C1 C2 C3 C4 . . . . -178.7(3) ?
C2 C3 C4 C5 . . . . -0.7(4) ?
C3 C4 C5 C6 . . . . 0.7(4) ?
C4 C5 C6 C7 . . . . -0.1(4) ?
C5 C6 C7 C2 . . . . -0.5(4) ?
C5 C6 C7 C8 . . . . 179.4(3) ?
C3 C2 C7 C6 . . . . 0.5(4) ?
C1 C2 C7 C6 . . . . 179.5(2) ?
C3 C2 C7 C8 . . . . -179.4(2) ?
C1 C2 C7 C8 . . . . -0.4(3) ?
C1 N1 C8 O2 . . . . -178.4(2) ?
C9 N1 C8 O2 . . . . -6.0(4) ?
C1 N1 C8 C7 . . . . 2.0(3) ?
C9 N1 C8 C7 . . . . 174.5(2) ?
C6 C7 C8 O2 . . . . -0.4(5) ?
C2 C7 C8 O2 . . . . 179.5(3) ?
C6 C7 C8 N1 . . . . 179.1(3) ?
C2 C7 C8 N1 . . . . -1.0(3) ?
C8 N1 C9 C10 . . . . 100.0(3) ?
C1 N1 C9 C10 . . . . -88.4(3) ?
N1 C9 C10 F3 . . . . 61.7(3) ?
N1 C9 C10 F1 . . . . -59.5(3) ?
N1 C9 C10 F2 . . . . -178.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 228748
2 PubChem 260614
