#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/73/2217350.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_2217350
loop_
_publ_author_name
'Zhou Jiang'
'Jun-Dong Wang'
'Nai-Sheng Chen'
'Jin-Ling Huang'
_publ_section_title
;
 2-Benzylisoindoline-1,3-dione: a monoclinic polymorph
;
_journal_coeditor_code           TK2231
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o324
_journal_page_last               o324
_journal_paper_doi               10.1107/S1600536807065336
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H11 N1 O2'
_chemical_formula_moiety         'C15 H11 N1 O2'
_chemical_formula_sum            'C15 H11 N O2'
_chemical_formula_weight         237.25
_chemical_name_common
;
N-benzylphthalimide
;
_chemical_name_systematic
;
2-Benzylisoindoline-1,3-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 98.851(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8324(6)
_cell_length_b                   5.3656(4)
_cell_length_c                   25.1926(18)
_cell_measurement_reflns_used    3962
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.2
_cell_volume                     1179.69(15)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2006)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2006)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2006)'
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.057
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            3668
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.04
_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    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.19
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.26
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.26
_refine_ls_R_factor_all          0.140
_refine_ls_R_factor_gt           0.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0216P)²+2.0256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.171
_refine_ls_wR_factor_ref         0.192
_reflns_number_gt                1439
_reflns_number_total             2083
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2231.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C15 H11 N1 O2'
_cod_database_code               2217350
_cod_database_fobs_code          2217350
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, 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_occupancy
O O2 0.5810(4) 0.7318(7) 0.08609(13) 0.0656(10) Uani d 1
N N1 0.7327(4) 1.0824(8) 0.09212(14) 0.0520(11) Uani d 1
O O1 0.8908(4) 1.4018(7) 0.07261(13) 0.0679(11) Uani d 1
H H1 0.579(6) 0.595(10) -0.030(2) 0.081 Uiso d 1
H H5 0.631(6) 1.076(10) 0.1573(18) 0.070(15) Uiso d 1
H H10 1.040(6) 1.130(11) 0.309(2) 0.085 Uiso d 1
H H4 0.895(6) 1.300(11) -0.042(2) 0.085 Uiso d 1
H H6 0.717(7) 1.326(13) 0.149(2) 0.11(2) Uiso d 1
H H11 0.834(6) 1.292(12) 0.244(2) 0.10(2) Uiso d 1
H H9 1.167(6) 0.743(11) 0.291(2) 0.090(18) Uiso d 1
H H2 0.666(6) 0.677(11) -0.112(2) 0.082(17) Uiso d 1
H H3 0.815(6) 1.037(10) -0.120(2) 0.081(16) Uiso d 1
H H8 1.099(7) 0.588(12) 0.204(2) 0.10(2) Uiso d 1
H H7 0.905(7) 0.729(12) 0.140(2) 0.115 Uiso d 1
C C1 0.7860(5) 1.0946(9) 0.00582(17) 0.0476(12) Uani d 1
C C2 0.6932(5) 0.8927(9) 0.00966(17) 0.0483(12) Uani d 1
C C3 0.6470(6) 0.7357(11) -0.0330(2) 0.0599(14) Uani d 1
C C4 0.6984(7) 0.7930(12) -0.0809(2) 0.0670(15) Uani d 1
C C5 0.7910(6) 0.9958(12) -0.0849(2) 0.0676(16) Uani d 1
C C6 0.8377(6) 1.1518(11) -0.0419(2) 0.0600(14) Uani d 1
C C7 0.8157(5) 1.2218(9) 0.05865(18) 0.0495(12) Uani d 1
C C8 0.6581(5) 0.8804(10) 0.06590(18) 0.0509(12) Uani d 1
C C9 0.7296(7) 1.1484(13) 0.1487(2) 0.0620(14) Uani d 1
C C10 0.8568(5) 1.0365(9) 0.18740(17) 0.0495(12) Uani d 1
C C11 0.8977(7) 1.1438(12) 0.2375(2) 0.0652(15) Uani d 1
C C12 1.0108(8) 1.0414(13) 0.2747(2) 0.0787(19) Uani d 1
C C13 1.0886(7) 0.8336(13) 0.2625(2) 0.0744(17) Uani d 1
C C14 1.0491(7) 0.7241(13) 0.2137(2) 0.0711(16) Uani d 1
C C15 0.9351(6) 0.8245(10) 0.1757(2) 0.0581(13) Uani d 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 C7 112.5(4)
C8 N1 C9 124.9(4)
C7 N1 C9 122.6(4)
C2 C1 C6 121.1(4)
C2 C1 C7 109.0(4)
C6 C1 C7 129.8(5)
C1 C2 C3 122.5(4)
C1 C2 C8 108.3(4)
C3 C2 C8 129.2(5)
C2 C3 C4 116.5(5)
C2 C3 H1 122(3)
C4 C3 H1 122(3)
C5 C4 C3 121.1(5)
C5 C4 H2 123(3)
C3 C4 H2 116(3)
C4 C5 C6 122.1(5)
C4 C5 H3 117(3)
C6 C5 H3 120(3)
C5 C6 C1 116.7(5)
C5 C6 H4 127(3)
C1 C6 H4 116(3)
O1 C7 N1 124.6(4)
O1 C7 C1 130.6(5)
N1 C7 C1 104.8(4)
O2 C8 N1 125.0(4)
O2 C8 C2 129.7(5)
N1 C8 C2 105.3(4)
N1 C9 C10 114.2(4)
N1 C9 H5 105(3)
C10 C9 H5 107(3)
N1 C9 H6 105(4)
C10 C9 H6 118(4)
H5 C9 H6 106(5)
C11 C10 C15 117.8(5)
C11 C10 C9 119.5(5)
C15 C10 C9 122.7(4)
C12 C11 C10 121.1(6)
C12 C11 H11 124(3)
C10 C11 H11 114(3)
C13 C12 C11 120.5(6)
C13 C12 H10 121(3)
C11 C12 H10 118(3)
C14 C13 C12 119.2(6)
C14 C13 H9 118(3)
C12 C13 H9 122(3)
C13 C14 C15 121.0(6)
C13 C14 H8 122(4)
C15 C14 H8 117(4)
C14 C15 C10 120.4(5)
C14 C15 H7 118(3)
C10 C15 H7 122(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C8 1.210(5)
N1 C8 1.383(6)
N1 C7 1.413(6)
N1 C9 1.473(6)
O1 C7 1.193(5)
C1 C2 1.371(6)
C1 C6 1.384(6)
C1 C7 1.483(6)
C2 C3 1.377(7)
C2 C8 1.498(6)
C3 C4 1.388(7)
C3 H1 0.98(5)
C4 C5 1.374(8)
C4 H2 1.00(5)
C5 C6 1.382(7)
C5 H3 0.97(5)
C6 H4 0.94(6)
C9 C10 1.496(7)
C9 H5 1.01(5)
C9 H6 0.96(7)
C10 C11 1.383(6)
C10 C15 1.386(7)
C11 C12 1.376(8)
C11 H11 1.00(6)
C12 C13 1.370(8)
C12 H10 0.99(5)
C13 C14 1.359(8)
C13 H9 1.04(6)
C14 C15 1.385(7)
C14 H8 0.91(6)
C15 H7 1.03(6)
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
C15 H7 O1 1_545 1.03(6) 2.43(6) 3.425(6) 161(5)
C3 H1 O2 3_665 0.98(5) 2.54(5) 3.363(7) 142(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 67611
