#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/66/2216635.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_2216635
loop_
_publ_author_name
'Maliha, Bushra'
'Hussain, Ishtiaq'
'Siddiqui, Hamid Latif'
'Tariq, Muhammad Ilyas'
'Parvez, Masood'
_publ_section_title
;
 1-Oxo-N-phenylisoindoline-2-carboxamide
;
_journal_coeditor_code           LH2558
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4728
_journal_page_last               o4728
_journal_paper_doi               10.1107/S1600536807056929
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H12 N2 O2'
_chemical_formula_moiety         'C15 H12 N2 O2'
_chemical_formula_sum            'C15 H12 N2 O2'
_chemical_formula_weight         252.27
_chemical_name_common
;
?
;
_chemical_name_systematic
;
1-Oxo-N-phenylisoindoline-2-carboxamide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.228(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.905(4)
_cell_length_b                   5.6190(10)
_cell_length_c                   17.161(6)
_cell_measurement_reflns_used    5034
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.62
_cell_volume                     1216.2(6)
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' ω and φ '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5034
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0384
_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)+(0.038P)²+0.39P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                2119
_reflns_number_total             2768
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2558.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216635
_cod_database_fobs_code          2216635
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
O O1 0.92562(7) -0.27832(16) 0.39885(5) 0.0328(2) Uani d . 1
O O2 0.89390(8) 0.31349(17) 0.24855(6) 0.0406(3) Uani d . 1
N N1 0.97796(8) 0.07840(18) 0.34984(6) 0.0263(2) Uani d . 1
N N2 0.80821(8) -0.01677(19) 0.28210(6) 0.0297(3) Uani d . 1
H H2N 0.8169 -0.1366 0.3159 0.036 Uiso calc R 1
C C1 1.09874(10) -0.1015(2) 0.44905(7) 0.0268(3) Uani d . 1
C C2 1.14801(11) -0.2514(2) 0.51004(8) 0.0315(3) Uani d . 1
H H2 1.1139 -0.3908 0.5234 0.038 Uiso calc R 1
C C3 1.24880(11) -0.1894(3) 0.55062(8) 0.0356(3) Uani d . 1
H H3 1.2846 -0.2866 0.5932 0.043 Uiso calc R 1
C C4 1.29830(11) 0.0143(3) 0.52972(8) 0.0380(3) Uani d . 1
H H4 1.3676 0.0532 0.5584 0.046 Uiso calc R 1
C C5 1.24877(11) 0.1619(2) 0.46793(8) 0.0346(3) Uani d . 1
H H5 1.2834 0.2991 0.4535 0.041 Uiso calc R 1
C C6 1.14717(10) 0.1021(2) 0.42818(7) 0.0281(3) Uani d . 1
C C7 1.07353(10) 0.2269(2) 0.36116(8) 0.0296(3) Uani d . 1
H H7A 1.0587 0.3916 0.3761 0.036 Uiso calc R 1
H H7B 1.1030 0.2308 0.3124 0.036 Uiso calc R 1
C C8 0.99162(10) -0.1207(2) 0.39860(7) 0.0263(3) Uani d . 1
C C9 0.89044(10) 0.1374(2) 0.28902(7) 0.0284(3) Uani d . 1
C C10 0.71058(10) -0.0067(2) 0.22699(8) 0.0301(3) Uani d . 1
C C11 0.68394(11) 0.1681(3) 0.16870(8) 0.0360(3) Uani d . 1
H H11 0.7324 0.2927 0.1648 0.043 Uiso calc R 1
C C12 0.58577(11) 0.1588(3) 0.11620(9) 0.0419(4) Uani d . 1
H H12 0.5675 0.2784 0.0765 0.050 Uiso calc R 1
C C13 0.51455(12) -0.0206(3) 0.12064(9) 0.0452(4) Uani d . 1
H H13 0.4481 -0.0259 0.0840 0.054 Uiso calc R 1
C C14 0.54067(12) -0.1927(3) 0.17890(10) 0.0480(4) Uani d . 1
H H14 0.4916 -0.3158 0.1828 0.058 Uiso calc R 1
C C15 0.63785(11) -0.1869(3) 0.23162(9) 0.0401(3) Uani d . 1
H H15 0.6552 -0.3067 0.2713 0.048 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C9 128.19(10)
C8 N1 C7 112.54(10)
C9 N1 C7 118.99(10)
C9 N2 C10 127.29(11)
C9 N2 H2N 116.4
C10 N2 H2N 116.4
C6 C1 C2 122.40(12)
C6 C1 C8 109.11(11)
C2 C1 C8 128.47(12)
C3 C2 C1 117.27(12)
C3 C2 H2 121.4
C1 C2 H2 121.4
C2 C3 C4 120.69(13)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 121.61(13)
C5 C4 H4 119.2
C3 C4 H4 119.2
C6 C5 C4 117.71(13)
C6 C5 H5 121.1
C4 C5 H5 121.1
C5 C6 C1 120.30(12)
C5 C6 C7 130.05(12)
C1 C6 C7 109.66(11)
N1 C7 C6 102.34(10)
N1 C7 H7A 111.3
C6 C7 H7A 111.3
N1 C7 H7B 111.3
C6 C7 H7B 111.3
H7A C7 H7B 109.2
O1 C8 N1 125.74(12)
O1 C8 C1 128.03(11)
N1 C8 C1 106.22(10)
O2 C9 N2 126.40(12)
O2 C9 N1 119.71(12)
N2 C9 N1 113.89(11)
C11 C10 C15 119.12(13)
C11 C10 N2 124.12(12)
C15 C10 N2 116.75(12)
C12 C11 C10 119.41(13)
C12 C11 H11 120.3
C10 C11 H11 120.3
C13 C12 C11 121.24(14)
C13 C12 H12 119.4
C11 C12 H12 119.4
C12 C13 C14 119.29(14)
C12 C13 H13 120.4
C14 C13 H13 120.4
C13 C14 C15 120.41(14)
C13 C14 H14 119.8
C15 C14 H14 119.8
C14 C15 C10 120.52(14)
C14 C15 H15 119.7
C10 C15 H15 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.2293(15)
O2 C9 1.2148(16)
N1 C8 1.3859(15)
N1 C9 1.4057(17)
N1 C7 1.4676(16)
N2 C9 1.3556(16)
N2 C10 1.4073(17)
N2 H2N 0.8800
C1 C6 1.3865(17)
C1 C2 1.3883(18)
C1 C8 1.4715(18)
C2 C3 1.384(2)
C2 H2 0.9500
C3 C4 1.394(2)
C3 H3 0.9500
C4 C5 1.391(2)
C4 H4 0.9500
C5 C6 1.3851(19)
C5 H5 0.9500
C6 C7 1.5016(18)
C7 H7A 0.9900
C7 H7B 0.9900
C10 C11 1.3921(19)
C10 C15 1.3944(19)
C11 C12 1.391(2)
C11 H11 0.9500
C12 C13 1.377(2)
C12 H12 0.9500
C13 C14 1.380(2)
C13 H13 0.9500
C14 C15 1.383(2)
C14 H14 0.9500
C15 H15 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
C2 H2 O1 3_746 0.95 2.41 3.3105(17) 159.1
C7 H7B O2 2_745 0.99 2.57 3.0746(17) 111.5
C7 H7B N2 2_755 0.99 2.60 3.4695(18) 147.1
C11 H11 O2 . 0.95 2.27 2.8833(19) 121.5
N2 H2N O1 . 0.88 1.95 2.6803(15) 140.0
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
C6 C1 C2 C3 0.42(18)
C8 C1 C2 C3 -177.84(12)
C1 C2 C3 C4 -0.79(19)
C2 C3 C4 C5 0.1(2)
C3 C4 C5 C6 1.0(2)
C4 C5 C6 C1 -1.35(19)
C4 C5 C6 C7 178.64(13)
C2 C1 C6 C5 0.67(19)
C8 C1 C6 C5 179.23(11)
C2 C1 C6 C7 -179.32(11)
C8 C1 C6 C7 -0.76(13)
C8 N1 C7 C6 -3.79(13)
C9 N1 C7 C6 -178.24(10)
C5 C6 C7 N1 -177.34(13)
C1 C6 C7 N1 2.65(13)
C9 N1 C8 O1 -3.3(2)
C7 N1 C8 O1 -177.10(12)
C9 N1 C8 C1 177.28(11)
C7 N1 C8 C1 3.46(13)
C6 C1 C8 O1 178.97(12)
C2 C1 C8 O1 -2.6(2)
C6 C1 C8 N1 -1.61(13)
C2 C1 C8 N1 176.84(12)
C10 N2 C9 O2 0.3(2)
C10 N2 C9 N1 -179.59(11)
C8 N1 C9 O2 -175.71(12)
C7 N1 C9 O2 -2.24(17)
C8 N1 C9 N2 4.20(17)
C7 N1 C9 N2 177.67(10)
C9 N2 C10 C11 0.9(2)
C9 N2 C10 C15 -179.93(12)
C15 C10 C11 C12 -0.3(2)
N2 C10 C11 C12 178.82(13)
C10 C11 C12 C13 -0.2(2)
C11 C12 C13 C14 0.8(2)
C12 C13 C14 C15 -0.8(3)
C13 C14 C15 C10 0.3(2)
C11 C10 C15 C14 0.2(2)
N2 C10 C15 C14 -178.95(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21120311
