#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226610.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_2226610
loop_
_publ_author_name
'Fu, Xian-Shu'
'Yu, Xiao-Ping'
'Wang, Wei-Min'
'Lin, Fang'
_publ_section_title
;
 N-(3,4-Difluorophenyl)phthalimide
;
_journal_coeditor_code           NG2786
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1809
_journal_paper_doi               10.1107/S1600536810024189
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H7 F2 N O2'
_chemical_formula_moiety         'C14 H7 F2 N O2'
_chemical_formula_sum            'C14 H7 F2 N O2'
_chemical_formula_weight         259.21
_chemical_name_systematic
;
N-(3,4-Difluorophenyl)phthalimide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.101(3)
_cell_length_b                   5.8093(12)
_cell_length_c                   24.866(5)
_cell_measurement_reflns_used    5269
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.863
_cell_measurement_theta_min      1.638
_cell_volume                     2181.4(8)
_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  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14468
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.06
_refine_ls_extinction_coef       0.046(4)
_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   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0399
_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)+(0.0736P)²+0.7186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                1780
_reflns_number_total             1920
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2786.cif
_cod_data_source_block           I
_cod_database_code               2226610
_cod_database_fobs_code          2226610
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.18581(6) 0.83152(17) 0.21976(4) 0.0398(3) Uani d . 1 . .
F F2 0.12250(7) 0.45784(18) 0.17125(4) 0.0409(3) Uani d . 1 . .
O O1 0.04193(7) 0.85824(18) 0.40561(4) 0.0289(3) Uani d . 1 . .
O O2 0.19778(7) 0.17995(18) 0.40802(4) 0.0282(3) Uani d . 1 . .
N N1 0.11557(7) 0.5119(2) 0.39257(5) 0.0217(3) Uani d . 1 . .
C C1 0.08090(9) 0.6931(2) 0.42336(6) 0.0221(4) Uani d . 1 . .
C C2 0.10111(9) 0.6332(3) 0.48041(6) 0.0223(4) Uani d . 1 . .
C C3 0.08065(10) 0.7479(3) 0.52755(6) 0.0277(4) Uani d . 1 . .
H H3 0.0499 0.8905 0.5271 0.033 Uiso calc R 1 . .
C C4 0.10706(10) 0.6458(3) 0.57568(6) 0.0315(4) Uani d . 1 . .
H H4 0.0942 0.7206 0.6087 0.038 Uiso calc R 1 . .
C C5 0.15184(10) 0.4367(3) 0.57625(6) 0.0314(4) Uani d . 1 . .
H H5 0.1688 0.3708 0.6097 0.038 Uiso calc R 1 . .
C C6 0.17221(10) 0.3224(3) 0.52856(6) 0.0276(4) Uani d . 1 . .
H H6 0.2028 0.1794 0.5287 0.033 Uiso calc R 1 . .
C C7 0.14620(9) 0.4251(3) 0.48107(6) 0.0225(4) Uani d . 1 . .
C C8 0.15903(9) 0.3464(2) 0.42484(6) 0.0218(4) Uani d . 1 . .
C C9 0.11494(9) 0.5016(3) 0.33528(6) 0.0232(4) Uani d . 1 . .
C C10 0.15100(9) 0.6824(3) 0.30585(6) 0.0251(4) Uani d . 1 . .
H H10 0.1744 0.8147 0.3232 0.030 Uiso calc R 1 . .
C C11 0.15153(9) 0.6626(3) 0.25060(6) 0.0276(4) Uani d . 1 . .
C C12 0.11839(10) 0.4696(3) 0.22544(6) 0.0284(4) Uani d . 1 . .
C C13 0.08237(10) 0.2919(3) 0.25441(6) 0.0297(4) Uani d . 1 . .
H H13 0.0591 0.1601 0.2367 0.036 Uiso calc R 1 . .
C C14 0.08046(9) 0.3082(3) 0.31032(6) 0.0262(4) Uani d . 1 . .
H H14 0.0557 0.1874 0.3312 0.031 Uiso calc R 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'
F F 0.0171 0.0103 '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
C1 N1 C8 . . 111.94(12) ?
C1 N1 C9 . . 125.04(12) ?
C8 N1 C9 . . 122.80(12) ?
O1 C1 N1 . . 125.29(13) ?
O1 C1 C2 . . 129.18(13) ?
N1 C1 C2 . . 105.51(12) ?
C3 C2 C7 . . 121.30(14) ?
C3 C2 C1 . . 130.35(14) ?
C7 C2 C1 . . 108.34(12) ?
C2 C3 C4 . . 117.29(15) ?
C2 C3 H3 . . 121.4 ?
C4 C3 H3 . . 121.4 ?
C5 C4 C3 . . 121.32(14) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 121.00(15) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C7 C6 C5 . . 117.33(15) ?
C7 C6 H6 . . 121.3 ?
C5 C6 H6 . . 121.3 ?
C6 C7 C2 . . 121.76(14) ?
C6 C7 C8 . . 129.48(14) ?
C2 C7 C8 . . 108.76(12) ?
O2 C8 N1 . . 125.03(13) ?
O2 C8 C7 . . 129.63(13) ?
N1 C8 C7 . . 105.34(12) ?
C14 C9 C10 . . 121.58(15) ?
C14 C9 N1 . . 118.96(14) ?
C10 C9 N1 . . 119.44(13) ?
C11 C10 C9 . . 117.63(14) ?
C11 C10 H10 . . 121.2 ?
C9 C10 H10 . . 121.2 ?
F1 C11 C10 . . 120.55(14) ?
F1 C11 C12 . . 118.25(14) ?
C10 C11 C12 . . 121.19(14) ?
F2 C12 C13 . . 120.28(14) ?
F2 C12 C11 . . 118.50(14) ?
C13 C12 C11 . . 121.21(14) ?
C12 C13 C14 . . 118.75(14) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C9 C14 C13 . . 119.63(14) ?
C9 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
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 C11 . 1.3486(18) ?
F2 C12 . 1.3507(17) ?
O1 C1 . 1.2088(17) ?
O2 C8 . 1.2051(18) ?
N1 C1 . 1.4032(18) ?
N1 C8 . 1.4139(18) ?
N1 C9 . 1.4257(19) ?
C1 C2 . 1.4923(19) ?
C2 C3 . 1.383(2) ?
C2 C7 . 1.388(2) ?
C3 C4 . 1.394(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.390(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.394(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.380(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.484(2) ?
C9 C14 . 1.385(2) ?
C9 C10 . 1.391(2) ?
C10 C11 . 1.379(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.378(2) ?
C12 C13 . 1.371(2) ?
C13 C14 . 1.394(2) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
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
C4 H4 F2 7_576 0.95 2.47 3.317(2) 149 yes
C5 H5 F2 7_566 0.95 2.54 3.321(2) 139 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 . . . . 178.83(13) ?
C9 N1 C1 O1 . . . . 4.1(2) ?
C8 N1 C1 C2 . . . . -2.26(14) ?
C9 N1 C1 C2 . . . . -177.01(12) ?
O1 C1 C2 C3 . . . . 0.4(3) ?
N1 C1 C2 C3 . . . . -178.49(14) ?
O1 C1 C2 C7 . . . . 179.19(14) ?
N1 C1 C2 C7 . . . . 0.34(15) ?
C7 C2 C3 C4 . . . . -0.1(2) ?
C1 C2 C3 C4 . . . . 178.61(14) ?
C2 C3 C4 C5 . . . . -0.2(2) ?
C3 C4 C5 C6 . . . . 0.3(2) ?
C4 C5 C6 C7 . . . . 0.0(2) ?
C5 C6 C7 C2 . . . . -0.4(2) ?
C5 C6 C7 C8 . . . . 179.47(14) ?
C3 C2 C7 C6 . . . . 0.4(2) ?
C1 C2 C7 C6 . . . . -178.56(13) ?
C3 C2 C7 C8 . . . . -179.47(13) ?
C1 C2 C7 C8 . . . . 1.58(16) ?
C1 N1 C8 O2 . . . . -176.48(13) ?
C9 N1 C8 O2 . . . . -1.6(2) ?
C1 N1 C8 C7 . . . . 3.18(14) ?
C9 N1 C8 C7 . . . . 178.07(12) ?
C6 C7 C8 O2 . . . . -3.1(3) ?
C2 C7 C8 O2 . . . . 176.76(14) ?
C6 C7 C8 N1 . . . . 177.27(14) ?
C2 C7 C8 N1 . . . . -2.88(15) ?
C1 N1 C9 C14 . . . . -127.38(15) ?
C8 N1 C9 C14 . . . . 58.42(17) ?
C1 N1 C9 C10 . . . . 54.38(18) ?
C8 N1 C9 C10 . . . . -119.82(15) ?
C14 C9 C10 C11 . . . . -0.1(2) ?
N1 C9 C10 C11 . . . . 178.06(12) ?
C9 C10 C11 F1 . . . . -179.79(12) ?
C9 C10 C11 C12 . . . . -0.7(2) ?
F1 C11 C12 F2 . . . . 0.6(2) ?
C10 C11 C12 F2 . . . . -178.55(13) ?
F1 C11 C12 C13 . . . . -179.79(13) ?
C10 C11 C12 C13 . . . . 1.1(2) ?
F2 C12 C13 C14 . . . . 179.01(13) ?
C11 C12 C13 C14 . . . . -0.6(2) ?
C10 C9 C14 C13 . . . . 0.6(2) ?
N1 C9 C14 C13 . . . . -177.63(12) ?
C12 C13 C14 C9 . . . . -0.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745390
2 PubChem 91011723
