#------------------------------------------------------------------------------
#$Date: 2022-02-09 11:59:13 +0200 (Wed, 09 Feb 2022) $
#$Revision: 272873 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/45/8104553.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_8104553
loop_
_publ_author_name
'Zhang, Wei'
'Zhang, Yu'
'Feng, Song-Hao'
'Wang, Jing-Jing'
_publ_section_title
;
 The crystal structure of 5-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione,
 C17H9ClN2O2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1155
_journal_page_last               1156
_journal_paper_doi               10.1515/ncrs-2021-0256
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C17 H9 Cl N2 O2'
_chemical_formula_sum            'C17 H9 Cl N2 O2'
_chemical_formula_weight         308.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                74.627(6)
_cell_angle_beta                 78.654(5)
_cell_angle_gamma                63.569(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8944(4)
_cell_length_b                   8.0678(5)
_cell_length_c                   12.6285(9)
_cell_measurement_reflns_used    2560
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2800
_cell_measurement_theta_min      6.2390
_cell_volume                     691.58(8)
_computing_cell_refinement
'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015) [1]'
_computing_data_collection
'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015) [1]'
_computing_data_reduction
'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015) [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [4]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -62.00  29.00   1.00    2.00    --  -40.30  57.00 -30.00   91
  2  ω     16.00  43.00   1.00    2.00    --   40.30 -99.00  90.00   27
  3  ω     51.00  77.00   1.00    2.00    --   40.30 -99.00  90.00   26
  4  ω     59.00  86.00   1.00    2.00    --   40.30-125.00   0.00   27
  5  ω     31.00  60.00   1.00    8.00    --  107.14 -95.00 -60.00   29
  6  ω     75.00 103.00   1.00    8.00    --  107.14 -95.00 -60.00   28
  7  ω     58.00  85.00   1.00    8.00    --  107.14 -61.00  30.00   27
  8  ω     46.00 133.00   1.00    8.00    --  107.14 -30.00 -60.00   87
  9  ω    103.00 173.00   1.00    8.00    --  107.14  45.00 -30.00   70
 10  ω    125.00 172.00   1.00    8.00    --  107.14 125.00 -60.00   47
 11  ω    134.00 178.00   1.00    8.00    --  107.14 125.00-180.00   44
 12  ω    107.00 149.00   1.00    8.00    --  107.14 125.00 -90.00   42
 13  ω     28.00 152.00   1.00    8.00    --  107.14 -15.00 150.00  124
 14  ω     34.00 121.00   1.00    8.00    --  107.14-125.00 150.00   87
 15  ω     50.00 123.00   1.00    8.00    --  107.14 -61.00 -90.00   73
 16  ω     37.00  95.00   1.00    8.00    --  107.14 -95.00-120.00   58
 17  ω   -103.00 -12.00   1.00    2.00    --  -40.30 -57.00  60.00   91
 18  ω   -109.00 -17.00   1.00    2.00    --  -40.30 -57.00-180.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0241956000
_diffrn_orient_matrix_UB_12      0.0447850000
_diffrn_orient_matrix_UB_13      -0.1239448000
_diffrn_orient_matrix_UB_21      -0.0479854000
_diffrn_orient_matrix_UB_22      -0.1711258000
_diffrn_orient_matrix_UB_23      0.0167874000
_diffrn_orient_matrix_UB_31      -0.2121372000
_diffrn_orient_matrix_UB_32      0.1269680000
_diffrn_orient_matrix_UB_33      0.0222896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4378
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.600
_diffrn_reflns_theta_min         3.645
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0431
_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)+(0.0778P)²+0.1512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2519
_reflns_number_total             2684
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0256_suppl.cif
_cod_data_source_block           1
_cod_database_code               8104553
_chemical_oxdiff_formula         'C H O N'
_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_max   0.769
_shelx_estimated_absorpt_t_min   0.619
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.715
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.09394(8) 0.82222(8) 0.74406(4) 0.0689(2) Uani 1 1 d . . . . .
O1 O 0.09789(19) 0.6497(2) 0.21944(12) 0.0584(4) Uani 1 1 d . . . . .
O2 O 0.51686(19) 0.6988(2) 0.39965(13) 0.0654(4) Uani 1 1 d . . . . .
N1 N 0.34452(19) 0.6585(2) 0.28782(12) 0.0443(3) Uani 1 1 d . . . . .
N2 N 0.5263(2) 0.2934(2) 0.24958(13) 0.0492(4) Uani 1 1 d . . . . .
C1 C 0.0678(2) 0.7107(2) 0.40240(14) 0.0413(3) Uani 1 1 d . . . . .
C2 C 0.1957(2) 0.7235(2) 0.45732(14) 0.0415(4) Uani 1 1 d . . . . .
C3 C 0.5698(2) 0.4297(2) 0.17598(14) 0.0417(4) Uani 1 1 d . . . . .
C4 C 0.1609(2) 0.6690(2) 0.29257(14) 0.0433(4) Uani 1 1 d . . . . .
C5 C 0.3747(2) 0.6934(2) 0.38365(15) 0.0448(4) Uani 1 1 d . . . . .
C6 C 0.4822(2) 0.6172(2) 0.19531(14) 0.0439(4) Uani 1 1 d . . . . .
C7 C 0.7000(2) 0.3942(3) 0.08110(15) 0.0468(4) Uani 1 1 d . . . . .
C8 C 0.1516(2) 0.7578(3) 0.56276(15) 0.0478(4) Uani 1 1 d . . . . .
H8 H 0.237623 0.766199 0.599639 0.057 Uiso 1 1 calc R . . . .
C9 C -0.0294(3) 0.7790(2) 0.61070(15) 0.0483(4) Uani 1 1 d . . . . .
C10 C -0.1596(3) 0.7666(3) 0.55747(16) 0.0510(4) Uani 1 1 d . . . . .
H10 H -0.278957 0.781186 0.592914 0.061 Uiso 1 1 calc R . . . .
C11 C -0.1116(2) 0.7324(3) 0.45076(16) 0.0489(4) Uani 1 1 d . . . . .
H11 H -0.197367 0.724525 0.413400 0.059 Uiso 1 1 calc R . . . .
C12 C 0.5290(3) 0.7556(3) 0.12776(17) 0.0556(4) Uani 1 1 d . . . . .
H12 H 0.473255 0.876498 0.142816 0.067 Uiso 1 1 calc R . . . .
C13 C 0.7431(3) 0.5407(3) 0.01106(16) 0.0557(5) Uani 1 1 d . . . . .
H13 H 0.827275 0.517372 -0.051652 0.067 Uiso 1 1 calc R . . . .
C14 C 0.7854(3) 0.2064(3) 0.06340(18) 0.0581(5) Uani 1 1 d . . . . .
H14 H 0.869949 0.176299 0.001588 0.070 Uiso 1 1 calc R . . . .
C15 C 0.6128(3) 0.1211(3) 0.22912(19) 0.0581(5) Uani 1 1 d . . . . .
H15 H 0.585777 0.026217 0.278956 0.070 Uiso 1 1 calc R . . . .
C16 C 0.6618(3) 0.7165(3) 0.03485(18) 0.0619(5) Uani 1 1 d . . . . .
H16 H 0.694102 0.811649 -0.010451 0.074 Uiso 1 1 calc R . . . .
C17 C 0.7428(3) 0.0711(3) 0.1373(2) 0.0630(5) Uani 1 1 d . . . . .
H17 H 0.798944 -0.053042 0.127378 0.076 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C4 N1 C6 123.38(14) . .
C5 N1 C4 111.90(14) . .
C5 N1 C6 124.71(14) . .
C15 N2 C3 116.65(17) . .
C2 C1 C4 108.37(14) . .
C11 C1 C2 121.46(16) . .
C11 C1 C4 130.16(15) . .
C1 C2 C5 108.37(14) . .
C8 C2 C1 122.10(15) . .
C8 C2 C5 129.53(15) . .
N2 C3 C6 118.76(15) . .
N2 C3 C7 123.38(16) . .
C7 C3 C6 117.86(16) . .
O1 C4 N1 124.94(16) . .
O1 C4 C1 129.34(16) . .
N1 C4 C1 105.71(14) . .
O2 C5 N1 125.54(17) . .
O2 C5 C2 128.83(17) . .
N1 C5 C2 105.62(14) . .
C3 C6 N1 118.97(15) . .
C12 C6 N1 120.11(16) . .
C12 C6 C3 120.92(16) . .
C3 C7 C14 116.90(17) . .
C13 C7 C3 120.13(16) . .
C13 C7 C14 122.95(17) . .
C2 C8 C9 115.91(16) . .
C8 C9 Cl1 118.20(14) . .
C10 C9 Cl1 118.75(14) . .
C10 C9 C8 123.05(17) . .
C9 C10 C11 119.87(16) . .
C1 C11 C10 117.62(16) . .
C6 C12 C16 120.32(18) . .
C16 C13 C7 120.18(17) . .
C17 C14 C7 119.46(19) . .
N2 C15 C17 124.55(19) . .
C13 C16 C12 120.51(18) . .
C14 C17 C15 119.04(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C9 1.7417(18) .
O1 C4 1.204(2) .
O2 C5 1.200(2) .
N1 C4 1.404(2) .
N1 C5 1.398(2) .
N1 C6 1.429(2) .
N2 C3 1.364(2) .
N2 C15 1.319(3) .
C1 C2 1.384(2) .
C1 C4 1.484(2) .
C1 C11 1.380(2) .
C2 C5 1.490(2) .
C2 C8 1.378(2) .
C3 C6 1.423(2) .
C3 C7 1.417(2) .
C6 C12 1.359(3) .
C7 C13 1.407(3) .
C7 C14 1.418(3) .
C8 C9 1.391(3) .
C9 C10 1.385(3) .
C10 C11 1.392(3) .
C12 C16 1.412(3) .
C13 C16 1.362(3) .
C14 C17 1.356(3) .
C15 C17 1.404(3) .
