#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200045.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_2200045
loop_
_publ_author_name
'Lynch, Daniel E.'
'McClenaghan, Ian'
_publ_section_title
;
 N-(8-Quinolylamino)phthalimide
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o16
_journal_page_last               o17
_journal_paper_doi               10.1107/S1600536800018109
_journal_volume                  57
_journal_year                    2001
_chemical_formula_sum            'C17 H11 N3 O2'
_chemical_formula_weight         289.29
_chemical_name_systematic        8-(Isoindol-1,3-dione-2-yl)aminoquinoline
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.397(3)
_cell_length_b                   10.819(2)
_cell_length_c                   7.6737(15)
_cell_measurement_reflns_used    4257
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1361.3(4)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .070
_diffrn_reflns_av_sigmaI/netI    .0532
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8737
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .096
_exptl_absorpt_correction_T_max  .996
_exptl_absorpt_correction_T_min  .976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          .26
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .04
_refine_diff_density_max         .542
_refine_diff_density_min         -.442
_refine_ls_extinction_coef       .060(5)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         1676
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          .066
_refine_ls_R_factor_gt           .048
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0490P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .099
_reflns_number_gt                1350
_reflns_number_total             1676
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6002.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_cell_volume        1361.4(5)
_cod_database_code               2200045
_cod_database_fobs_code          2200045
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 -.09061(14) -.3749(2) .6464(3) .0275(5) Uani d . 1 . . N
C2 -.13724(18) -.4657(3) .7020(3) .0326(7) Uani d . 1 . . C
H2 -.1503 -.4681 .8226 .041 Uiso calc R 1 . . H
C3 -.16898(17) -.5594(2) .5953(4) .0343(7) Uani d . 1 . . C
H3 -.2015 -.6235 .6433 .043 Uiso calc R 1 . . H
C4 -.15233(18) -.5566(2) .4225(4) .0316(6) Uani d . 1 . . C
H4 -.1733 -.6191 .3480 .040 Uiso calc R 1 . . H
C5 -.08492(16) -.4502(2) .1746(3) .0306(7) Uani d . 1 . . C
H5 -.1041 -.5105 .0946 .038 Uiso calc R 1 . . H
C6 -.03895(17) -.3530(2) .1168(4) .0332(6) Uani d . 1 . . C
H6 -.0272 -.3456 -.0040 .041 Uiso calc R 1 . . H
C7 -.00890(16) -.2638(2) .2340(4) .0288(6) Uani d . 1 . . C
H7 .0232 -.1971 .1917 .036 Uiso calc R 1 . . H
C8 -.02552(16) -.2723(2) .4086(3) .0241(5) Uani d . 1 . . C
C9 -.07421(15) -.3708(2) .4719(3) .0230(6) Uani d . 1 . . C
C10 -.10386(17) -.4607(2) .3534(3) .0272(6) Uani d . 1 . . C
N81 -.00131(13) -.18119(19) .5284(3) .0263(5) Uani d . 1 . . N
H81 -.0055(16) -.208(3) .639(4) .031(8) Uiso d . 1 . . H
C11 .06871(16) .0046(2) .4219(3) .0258(6) Uani d . 1 . . C
O11 .00804(11) .06545(16) .3949(3) .0319(5) Uani d . 1 . . O
N12 .06876(12) -.11626(19) .4897(3) .0255(5) Uani d . 1 . . N
C13 .14796(17) -.1653(2) .5015(3) .0286(6) Uani d . 1 . . C
O13 .16305(12) -.26878(16) .5528(3) .0393(5) Uani d . 1 . . O
C14 .28647(16) -.0627(3) .4280(4) .0305(6) Uani d . 1 . . C
H14 .3189 -.1315 .4616 .038 Uiso calc R 1 . . H
C15 .32202(18) .0448(3) .3651(4) .0342(7) Uani d . 1 . . C
H15 .3797 .0498 .3554 .043 Uiso calc R 1 . . H
C16 .27438(17) .1451(3) .3162(4) .0334(7) Uani d . 1 . . C
H16 .3001 .2176 .2730 .042 Uiso calc R 1 . . H
C17 .19009(17) .1416(3) .3292(3) .0288(6) Uani d . 1 . . C
H17 .1576 .2104 .2961 .036 Uiso calc R 1 . . H
C18 .15523(16) .0348(2) .3918(3) .0255(6) Uani d . 1 . . C
C19 .20287(16) -.0664(2) .4402(3) .0256(6) Uani d . 1 . . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C2 N1 C9 117.1(2)
N1 C2 C3 124.5(3)
N1 C2 H2 117.8
C3 C2 H2 117.8
C4 C3 C2 118.7(3)
C4 C3 H3 120.6
C2 C3 H3 120.6
C3 C4 C10 119.9(3)
C3 C4 H4 120.0
C10 C4 H4 120.0
C6 C5 C10 119.9(3)
C6 C5 H5 120.0
C10 C5 H5 120.0
C5 C6 C7 120.8(3)
C5 C6 H6 119.6
C7 C6 H6 119.6
C8 C7 C6 120.6(2)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 N81 122.4(2)
C7 C8 C9 119.8(2)
N81 C8 C9 117.5(2)
N1 C9 C10 122.6(2)
N1 C9 C8 118.1(2)
C10 C9 C8 119.3(2)
C5 C10 C4 123.3(3)
C5 C10 C9 119.5(2)
C4 C10 C9 117.2(2)
N12 N81 C8 116.8(2)
N12 N81 H81 115.7(18)
C8 N81 H81 111.5(19)
O11 C11 N12 124.7(2)
O11 C11 C18 130.1(2)
N12 C11 C18 105.3(2)
N81 N12 C13 124.3(2)
N81 N12 C11 123.5(2)
C13 N12 C11 112.0(2)
O13 C13 N12 123.9(3)
O13 C13 C19 130.4(3)
N12 C13 C19 105.6(2)
C19 C14 C15 117.9(3)
C19 C14 H14 121.1
C15 C14 H14 121.1
C14 C15 C16 120.8(3)
C14 C15 H15 119.6
C16 C15 H15 119.6
C15 C16 C17 121.3(3)
C15 C16 H16 119.3
C17 C16 H16 119.3
C18 C17 C16 117.5(3)
C18 C17 H17 121.2
C16 C17 H17 121.2
C17 C18 C19 121.3(3)
C17 C18 C11 129.8(2)
C19 C18 C11 108.9(2)
C14 C19 C18 121.2(3)
C14 C19 C13 130.7(3)
C18 C19 C13 108.2(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
N1 C2 . 1.317(3) ?
N1 C9 . 1.367(3) ?
C2 C3 . 1.403(4) ?
C2 H2 . .9500 ?
C3 C4 . 1.354(4) ?
C3 H3 . .9500 ?
C4 C10 . 1.411(4) ?
C4 H4 . .9500 ?
C5 C6 . 1.368(4) ?
C5 C10 . 1.411(4) ?
C5 H5 . .9500 ?
C6 C7 . 1.408(4) ?
C6 H6 . .9500 ?
C7 C8 . 1.370(4) ?
C7 H7 . .9500 ?
C8 N81 . 1.405(3) ?
C8 C9 . 1.417(4) ?
C9 C10 . 1.417(3) ?
N81 N12 . 1.379(3) ?
N81 H81 . .90(3) ?
C11 O11 . 1.211(3) ?
C11 N12 . 1.407(3) ?
C11 C18 . 1.474(4) ?
N12 C13 . 1.406(3) ?
C13 O13 . 1.213(3) ?
C13 C19 . 1.475(4) ?
C14 C19 . 1.375(4) ?
C14 C15 . 1.387(4) ?
C14 H14 . .9500 ?
C15 C16 . 1.389(4) ?
C15 H15 . .9500 ?
C16 C17 . 1.386(4) ?
C16 H16 . .9500 ?
C17 C18 . 1.376(4) ?
C17 H17 . .9500 ?
C18 C19 . 1.395(4) ?
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
N81 H81 O11 2 .90(3) 2.50(3) 3.081(3) 123(2) yes
N81 H81 N1 1.555 .90(3) 2.28(3) 2.712(3) 109(2) yes
C17 H17 N1 2_554 .95 2.39 3.316(4) 166.2 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
C9 N1 C2 C3 1.8(4)
N1 C2 C3 C4 -1.2(5)
C2 C3 C4 C10 .0(4)
C10 C5 C6 C7 1.1(4)
C5 C6 C7 C8 -.3(4)
C6 C7 C8 N81 -175.8(2)
C6 C7 C8 C9 -.8(4)
C2 N1 C9 C10 -1.3(4)
C2 N1 C9 C8 178.7(2)
C7 C8 C9 N1 -178.9(2)
N81 C8 C9 N1 -3.7(4)
C7 C8 C9 C10 1.2(4)
N81 C8 C9 C10 176.4(2)
C6 C5 C10 C4 178.6(2)
C6 C5 C10 C9 -.7(4)
C3 C4 C10 C5 -178.9(3)
C3 C4 C10 C9 .3(4)
N1 C9 C10 C5 179.6(3)
C8 C9 C10 C5 -.4(4)
N1 C9 C10 C4 .3(4)
C8 C9 C10 C4 -179.7(2)
C7 C8 N81 N12 -29.9(4)
C9 C8 N81 N12 155.1(2)
C8 N81 N12 C13 -73.0(3)
C8 N81 N12 C11 102.4(3)
O11 C11 N12 N81 2.1(4)
C18 C11 N12 N81 -177.1(2)
O11 C11 N12 C13 178.1(3)
C18 C11 N12 C13 -1.1(3)
N81 N12 C13 O13 -2.5(4)
C11 N12 C13 O13 -178.4(2)
N81 N12 C13 C19 177.3(2)
C11 N12 C13 C19 1.4(3)
C19 C14 C15 C16 .0(4)
C14 C15 C16 C17 .3(4)
C15 C16 C17 C18 -.2(4)
C16 C17 C18 C19 -.1(4)
C16 C17 C18 C11 179.2(3)
O11 C11 C18 C17 1.9(5)
N12 C11 C18 C17 -179.0(3)
O11 C11 C18 C19 -178.7(3)
N12 C11 C18 C19 .4(3)
C15 C14 C19 C18 -.4(4)
C15 C14 C19 C13 -179.7(3)
C17 C18 C19 C14 .4(4)
C11 C18 C19 C14 -179.0(2)
C17 C18 C19 C13 179.9(2)
C11 C18 C19 C13 .5(3)
O13 C13 C19 C14 -1.9(5)
N12 C13 C19 C14 178.3(3)
O13 C13 C19 C18 178.7(3)
N12 C13 C19 C18 -1.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1223138
2 PubChem 1481940
