#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/24/8102410.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_8102410
loop_
_publ_author_name
'Su-Qing Wang'
'Fang-Fang Jian'
'Huan-Qiang Liu'
_publ_section_title
;
 Crystal structure of
 2-((1H-benzo[d]imidazol-1-yl)methyl)isoindoline-1,3-dione, C16H11N3O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              305
_journal_volume                  225
_journal_year                    2010
_chemical_formula_moiety         'C16 H11 N3 O2'
_chemical_formula_sum            'C16 H11 N3 O2'
_chemical_formula_weight         277.28
_chemical_name_systematic
; 
2-((1H-benzo[d]imidazol-1-yl)methyl)
isoindoline-1,3-dione
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                   10.5682(11)
_cell_length_b                   23.030(2)
_cell_length_c                   5.1985(5)
_cell_measurement_reflns_used    1464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      1.77
_cell_volume                     1265.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7857
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_coef       0.0143(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0304
_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)+(0.0342P)²+0.0809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                1464
_reflns_number_total             1698
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2512.cff
_cod_data_source_block           p-1
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               8102410
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.11431(13) 0.78082(6) 0.3782(3) 0.0571(4) Uani 1 1 d . . .
O2 O 0.78430(13) 0.81468(6) -0.1680(3) 0.0543(4) Uani 1 1 d . . .
N1 N 0.90235(14) 0.68437(6) 0.0170(3) 0.0400(3) Uani 1 1 d . . .
N2 N 0.74352(14) 0.61977(7) 0.0072(4) 0.0465(4) Uani 1 1 d . . .
N3 N 0.95735(14) 0.78566(6) 0.0693(3) 0.0438(4) Uani 1 1 d . . .
C1 C 1.02773(17) 0.80639(8) 0.2793(4) 0.0429(5) Uani 1 1 d . . .
C2 C 0.97062(16) 0.86333(7) 0.3453(4) 0.0409(4) Uani 1 1 d . . .
C3 C 1.00210(18) 0.90263(8) 0.5350(4) 0.0485(5) Uani 1 1 d . . .
H3A H 1.0690 0.8959 0.6474 0.058 Uiso 1 1 calc R . .
C4 C 0.92919(19) 0.95274(8) 0.5505(5) 0.0525(5) Uani 1 1 d . . .
H4A H 0.9473 0.9799 0.6775 0.063 Uiso 1 1 calc R . .
C5 C 0.83059(18) 0.96330(9) 0.3826(4) 0.0525(5) Uani 1 1 d . . .
H5A H 0.7845 0.9975 0.3970 0.063 Uiso 1 1 calc R . .
C6 C 0.79946(18) 0.92346(8) 0.1927(4) 0.0465(4) Uani 1 1 d . . .
H6A H 0.7331 0.9303 0.0792 0.056 Uiso 1 1 calc R . .
C7 C 0.87054(16) 0.87337(7) 0.1786(4) 0.0401(4) Uani 1 1 d . . .
C8 C 0.85972(16) 0.82347(8) 0.0019(4) 0.0413(4) Uani 1 1 d . . .
C9 C 0.98181(19) 0.73192(8) -0.0676(4) 0.0470(5) Uani 1 1 d . . .
H9A H 0.9682 0.7383 -0.2500 0.056 Uiso 1 1 calc R . .
H9B H 1.0698 0.7212 -0.0437 0.056 Uiso 1 1 calc R . .
C10 C 0.79242(18) 0.66649(8) -0.0952(4) 0.0450(4) Uani 1 1 d . . .
H10A H 0.7554 0.6859 -0.2328 0.054 Uiso 1 1 calc R . .
C11 C 0.92779(16) 0.64517(7) 0.2120(4) 0.0381(4) Uani 1 1 d . . .
C12 C 1.02613(17) 0.64043(8) 0.3855(4) 0.0450(5) Uani 1 1 d . . .
H12A H 1.0916 0.6674 0.3901 0.054 Uiso 1 1 calc R . .
C13 C 1.02253(19) 0.59376(9) 0.5515(5) 0.0512(5) Uani 1 1 d . . .
H13A H 1.0871 0.5891 0.6712 0.061 Uiso 1 1 calc R . .
C14 C 0.92396(19) 0.55333(8) 0.5439(4) 0.0520(5) Uani 1 1 d . . .
H14A H 0.9249 0.5221 0.6573 0.062 Uiso 1 1 calc R . .
C15 C 0.82588(19) 0.55872(8) 0.3727(4) 0.0484(5) Uani 1 1 d . . .
H15A H 0.7600 0.5320 0.3706 0.058 Uiso 1 1 calc R . .
C16 C 0.82758(16) 0.60515(7) 0.2027(4) 0.0399(4) Uani 1 1 d . . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
_geom_angle_publ_flag
C10 N1 C11 106.37(14) . . ?
C10 N1 C9 126.34(18) . . ?
C11 N1 C9 127.08(16) . . ?
C10 N2 C16 104.14(15) . . ?
C8 N3 C1 112.02(15) . . ?
C8 N3 C9 122.74(17) . . ?
C1 N3 C9 125.23(16) . . ?
O1 C1 N3 124.63(18) . . ?
O1 C1 C2 130.00(19) . . ?
N3 C1 C2 105.36(15) . . ?
C3 C2 C7 121.43(17) . . ?
C3 C2 C1 130.34(18) . . ?
C7 C2 C1 108.23(16) . . ?
C2 C3 C4 116.90(19) . . ?
C2 C3 H3A 121.5 . . ?
C4 C3 H3A 121.5 . . ?
C5 C4 C3 121.88(19) . . ?
C5 C4 H4A 119.1 . . ?
C3 C4 H4A 119.1 . . ?
C4 C5 C6 120.81(19) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 117.53(19) . . ?
C7 C6 H6A 121.2 . . ?
C5 C6 H6A 121.2 . . ?
C6 C7 C2 121.44(18) . . ?
C6 C7 C8 129.99(18) . . ?
C2 C7 C8 108.56(15) . . ?
O2 C8 N3 124.60(18) . . ?
O2 C8 C7 129.59(17) . . ?
N3 C8 C7 105.80(15) . . ?
N1 C9 N3 113.13(16) . . ?
N1 C9 H9A 109.0 . . ?
N3 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
N3 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 N1 114.30(17) . . ?
N2 C10 H10A 122.8 . . ?
N1 C10 H10A 122.8 . . ?
C12 C11 N1 132.58(16) . . ?
C12 C11 C16 122.56(17) . . ?
N1 C11 C16 104.85(16) . . ?
C13 C12 C11 116.73(18) . . ?
C13 C12 H12A 121.6 . . ?
C11 C12 H12A 121.6 . . ?
C12 C13 C14 121.5(2) . . ?
C12 C13 H13A 119.3 . . ?
C14 C13 H13A 119.3 . . ?
C15 C14 C13 121.41(19) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C14 C15 C16 118.25(18) . . ?
C14 C15 H15A 120.9 . . ?
C16 C15 H15A 120.9 . . ?
C15 C16 N2 130.07(17) . . ?
C15 C16 C11 119.58(17) . . ?
N2 C16 C11 110.34(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.204(2) . yes
O2 C8 1.207(2) . yes
N1 C10 1.363(2) . ?
N1 C11 1.384(2) . ?
N1 C9 1.448(2) . ?
N2 C10 1.307(2) . ?
N2 C16 1.391(3) . ?
N3 C8 1.395(2) . ?
N3 C1 1.404(3) . ?
N3 C9 1.451(2) . ?
C1 C2 1.484(3) . ?
C2 C3 1.379(3) . ?
C2 C7 1.387(3) . ?
C3 C4 1.390(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.379(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.476(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(3) . ?
C11 C16 1.405(2) . ?
C12 C13 1.379(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.398(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.387(3) . ?
C15 H15A 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9B O2 0.97 2.50 3.412(2) 157.1 3_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5043961
