#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200156.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_2200156
loop_
_publ_author_name
'Holband, Jolanta'
'Jurkin, Magdalena'
'Wójcik, Grażyna'
'Holband, Tomasz'
_publ_section_title
;
 2-(5-Chloropyridin-2-yl)-2,3-dihydro-1H-isoindole-1,3-dione
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o250
_journal_page_last               o251
_journal_paper_doi               10.1107/S1600536801003026
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C13 H7 Cl N2 O2'
_chemical_formula_moiety         'C13 H7 Cl N2 O2'
_chemical_formula_sum            'C13 H7 Cl N2 O2'
_chemical_formula_weight         258.66
_chemical_name_systematic
;
1-(5-chloropyridin-2-yl)-isoindole-1,3-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                100.58(3)
_cell_angle_beta                 98.38(3)
_cell_angle_gamma                107.98(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4940(10)
_cell_length_b                   7.974(2)
_cell_length_c                   10.303(2)
_cell_measurement_reflns_used    1144
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.51
_cell_measurement_theta_min      3.39
_cell_volume                     562.0(2)
_computing_cell_refinement       'Kuma KM4CCD Software'
_computing_data_collection       'Kuma KM4CCD Software (Kuma, 1999)'
_computing_data_reduction        'Kuma KM4CCD Software'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full .945
_diffrn_measured_fraction_theta_max .945
_diffrn_measurement_device_type  'Kuma Diffraction KM4CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .016
_diffrn_reflns_av_sigmaI/netI    .0140
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3767
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         4.37
_exptl_absorpt_coefficient_mu    .333
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      1.530
_exptl_crystal_density_method    flotation
_exptl_crystal_description       Prism
_exptl_crystal_F_000             264
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .38
_exptl_crystal_size_min          .15
_refine_diff_density_max         .241
_refine_diff_density_min         -.274
_refine_ls_extinction_coef       .104(13)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          .0414
_refine_ls_R_factor_gt           .0403
_refine_ls_shift/su_max          .035
_refine_ls_shift/su_mean         .008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0757P)²+0.1249P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1195
_reflns_number_gt                2244
_reflns_number_total             2342
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv6002.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.1249P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.1249P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        562.00(19)
_cod_database_code               2200156
_cod_database_fobs_code          2200156
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 .23507(6) .24785(6) .22275(4) .05818(19) Uani d . 1 . . Cl
O1 .26258(19) .43129(15) -.36847(11) .0515(3) Uani d . 1 . . O
O2 .26209(16) .93644(14) -.07226(10) .0456(3) Uani d . 1 . . O
N1 .12583(17) .39366(16) -.11877(12) .0392(3) Uani d . 1 . . N
N2 .24959(17) .65566(15) -.19346(12) .0367(3) Uani d . 1 . . N
C1 .25432(18) .83670(17) -.17756(14) .0350(3) Uani d . 1 . . C
C2 .24789(18) .87237(18) -.31399(13) .0350(3) Uani d . 1 . . C
C3 .2422(2) 1.02542(19) -.35652(15) .0413(3) Uani d . 1 . . C
H3 .2423 1.1280 -.2965 .050 Uiso calc R 1 . . H
C4 .2362(2) 1.0200(2) -.49305(16) .0479(4) Uani d . 1 . . C
H4 .2338 1.1214 -.5247 .058 Uiso calc R 1 . . H
C5 .2338(3) .8662(2) -.58266(16) .0515(4) Uani d . 1 . . C
H5 .2296 .8661 -.6733 .062 Uiso calc R 1 . . H
C6 .2377(3) .7120(2) -.53904(16) .0475(4) Uani d . 1 . . C
H6 .2348 .6081 -.5990 .057 Uiso calc R 1 . . H
C7 .2459(2) .71894(18) -.40381(14) .0376(3) Uani d . 1 . . C
C8 .2518(2) .57856(18) -.32855(14) .0375(3) Uani d . 1 . . C
C9 .24798(19) .56417(17) -.08728(14) .0339(3) Uani d . 1 . . C
C10 .36886(19) .65214(18) .03827(14) .0372(3) Uani d . 1 . . C
H10 .4504 .7721 .0555 .045 Uiso calc R 1 . . H
C11 .3641(2) .5556(2) .13710(14) .0393(3) Uani d . 1 . . C
H11 .4417 .6094 .2232 .047 Uiso calc R 1 . . H
C12 .2412(2) .37717(19) .10472(14) .0376(3) Uani d . 1 . . C
C13 .1248(2) .30049(19) -.02311(15) .0404(3) Uani d . 1 . . C
H13 .0431 .1802 -.0433 .048 Uiso calc R 1 . . H
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'
Cl Cl .1484 .1585 '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_publ_flag
C9 N1 C13 117.28(12) yes
C1 N2 C8 111.11(11) ?
C1 N2 C9 124.44(11) ?
C8 N2 C9 124.44(11) ?
O2 C1 N2 125.01(13) yes
O2 C1 C2 129.18(12) ?
N2 C1 C2 105.81(11) yes
C3 C2 C7 121.33(13) ?
C3 C2 C1 129.94(13) ?
C7 C2 C1 108.73(12) ?
C2 C3 C4 117.28(14) ?
C2 C3 H3 121.4 ?
C4 C3 H3 121.4 ?
C5 C4 C3 121.25(14) ?
C5 C4 H4 119.4 ?
C3 C4 H4 119.4 ?
C4 C5 C6 121.03(15) ?
C4 C5 H5 119.5 ?
C6 C5 H5 119.5 ?
C7 C6 C5 117.45(15) ?
C7 C6 H6 121.3 ?
C5 C6 H6 121.3 ?
C6 C7 C2 121.66(14) ?
C6 C7 C8 129.77(13) ?
C2 C7 C8 108.57(12) ?
O1 C8 N2 125.38(13) yes
O1 C8 C7 128.92(13) ?
N2 C8 C7 105.66(11) yes
N1 C9 C10 124.46(13) ?
N1 C9 N2 115.39(12) yes
C10 C9 N2 120.16(12) yes
C11 C10 C9 117.76(12) ?
C11 C10 H10 121.1 ?
C9 C10 H10 121.1 ?
C12 C11 C10 118.34(13) ?
C12 C11 H11 120.8 ?
C10 C11 H11 120.8 ?
C11 C12 C13 120.00(13) yes
C11 C12 Cl1 120.29(12) ?
C13 C12 Cl1 119.70(11) ?
N1 C13 C12 122.14(13) ?
N1 C13 H13 118.9 ?
C12 C13 H13 118.9 ?
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
Cl1 C12 . 1.7297(15) yes
O1 C8 . 1.2023(17) yes
O2 C1 . 1.2038(17) yes
N1 C9 . 1.3323(19) yes
N1 C13 . 1.3382(18) yes
N2 C1 . 1.4113(16) yes
N2 C8 . 1.4192(18) yes
N2 C9 . 1.4215(17) yes
C1 C2 . 1.4814(19) ?
C2 C3 . 1.3807(19) ?
C2 C7 . 1.3865(19) ?
C3 C4 . 1.393(2) ?
C3 H3 . .9300 ?
C4 C5 . 1.386(2) ?
C4 H4 . .9300 ?
C5 C6 . 1.392(2) ?
C5 H5 . .9300 ?
C6 C7 . 1.376(2) ?
C6 H6 . .9300 ?
C7 C8 . 1.4817(19) ?
C9 C10 . 1.385(2) yes
C10 C11 . 1.383(2) yes
C10 H10 . .9300 ?
C11 C12 . 1.383(2) yes
C11 H11 . .9300 ?
C12 C13 . 1.382(2) yes
C13 H13 . .9300 ?
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
_geom_torsion_publ_flag
C8 N2 C1 O2 -176.61(13) ?
C9 N2 C1 O2 1.8(2) yes
C8 N2 C1 C2 3.37(14) ?
C9 N2 C1 C2 -178.19(11) ?
O2 C1 C2 C3 -2.6(2) ?
N2 C1 C2 C3 177.42(14) ?
O2 C1 C2 C7 178.10(14) ?
N2 C1 C2 C7 -1.88(14) ?
C7 C2 C3 C4 -.6(2) ?
C1 C2 C3 C4 -179.81(13) ?
C2 C3 C4 C5 .7(2) ?
C3 C4 C5 C6 -.1(3) ?
C4 C5 C6 C7 -.7(3) ?
C5 C6 C7 C2 .8(2) ?
C5 C6 C7 C8 -179.93(15) ?
C3 C2 C7 C6 -.2(2) ?
C1 C2 C7 C6 179.17(13) ?
C3 C2 C7 C8 -179.59(12) ?
C1 C2 C7 C8 -.22(15) ?
C1 N2 C8 O1 174.39(14) ?
C9 N2 C8 O1 -4.0(2) ?
C1 N2 C8 C7 -3.50(15) ?
C9 N2 C8 C7 178.06(11) ?
C6 C7 C8 O1 5.1(3) ?
C2 C7 C8 O1 -175.56(15) ?
C6 C7 C8 N2 -177.11(15) ?
C2 C7 C8 N2 2.22(15) ?
C13 N1 C9 C10 -2.0(2) ?
C13 N1 C9 N2 177.65(11) ?
C1 N2 C9 N1 136.68(14) yes
C8 N2 C9 N1 -45.09(18) yes
C1 N2 C9 C10 -43.67(18) ?
C8 N2 C9 C10 134.57(14) ?
N1 C9 C10 C11 .9(2) ?
N2 C9 C10 C11 -178.75(11) ?
C9 C10 C11 C12 .7(2) ?
C10 C11 C12 C13 -1.0(2) ?
C10 C11 C12 Cl1 177.92(10) ?
C9 N1 C13 C12 1.6(2) ?
C11 C12 C13 N1 -.1(2) ?
Cl1 C12 C13 N1 -179.07(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 482628
