#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221681.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_2221681
loop_
_publ_author_name
'Liu, Guan-Feng'
'Luo, Yong-Wen'
'Qin, Da-Bin'
_publ_section_title
;
 N-Phenylanthranilic anhydride
;
_journal_coeditor_code           HB2927
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1043
_journal_paper_doi               10.1107/S1600536809013002
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C26 H20 N2 O3'
_chemical_formula_sum            'C26 H20 N2 O3'
_chemical_formula_weight         408.44
_chemical_name_systematic
;
N-Phenylanthranilic anhydride
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 100.594(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.090(3)
_cell_length_b                   21.056(6)
_cell_length_c                   10.623(3)
_cell_measurement_reflns_used    3250
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.40
_cell_volume                     1998.6(10)
_computing_cell_refinement       'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8102
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.40
_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            Colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0387
_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)+(0.0706P)²+0.28P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2000
_reflns_number_total             2275
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2927.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_cell_volume        1998.5(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2221681
_cod_database_fobs_code          2221681
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'
'-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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.11910(9) 0.38137(4) 0.34545(8) 0.0229(2) Uani d . 1 . .
O O2 0.0000 0.29421(5) 0.2500 0.0225(3) Uani d S 1 . .
N N1 0.41159(11) 0.37188(5) 0.43582(9) 0.0204(2) Uani d . 1 . .
C C1 0.56426(13) 0.43835(6) 0.59357(11) 0.0236(3) Uani d . 1 . .
H H1 0.4845 0.4399 0.6401 0.028 Uiso calc R 1 . .
C C2 0.69505(14) 0.47174(6) 0.63703(12) 0.0275(3) Uani d . 1 . .
H H2 0.7045 0.4964 0.7130 0.033 Uiso calc R 1 . .
C C3 0.81191(14) 0.46930(6) 0.57006(13) 0.0274(3) Uani d . 1 . .
H H3 0.9020 0.4918 0.6006 0.033 Uiso calc R 1 . .
C C4 0.79712(13) 0.43398(5) 0.45834(12) 0.0246(3) Uani d . 1 . .
H H4 0.8771 0.4324 0.4121 0.030 Uiso calc R 1 . .
C C5 0.66575(13) 0.40089(5) 0.41392(11) 0.0215(3) Uani d . 1 . .
H H5 0.6555 0.3771 0.3369 0.026 Uiso calc R 1 . .
C C6 0.54946(12) 0.40262(5) 0.48214(11) 0.0185(3) Uani d . 1 . .
C C7 0.39399(12) 0.30870(5) 0.40566(10) 0.0176(2) Uani d . 1 . .
C C8 0.51448(12) 0.26579(6) 0.43627(11) 0.0207(3) Uani d . 1 . .
H H8 0.6099 0.2811 0.4764 0.025 Uiso calc R 1 . .
C C9 0.49596(13) 0.20234(6) 0.40898(11) 0.0233(3) Uani d . 1 . .
H H9 0.5787 0.1744 0.4313 0.028 Uiso calc R 1 . .
C C10 0.35825(13) 0.17796(6) 0.34912(11) 0.0234(3) Uani d . 1 . .
H H10 0.3469 0.1339 0.3305 0.028 Uiso calc R 1 . .
C C11 0.23933(13) 0.21874(5) 0.31759(11) 0.0206(3) Uani d . 1 . .
H H11 0.1453 0.2025 0.2763 0.025 Uiso calc R 1 . .
C C12 0.25345(12) 0.28396(5) 0.34495(10) 0.0179(3) Uani d . 1 . .
C C13 0.12427(12) 0.32625(5) 0.31547(10) 0.0183(2) Uani d . 1 . .
H H1N 0.3269(17) 0.3947(7) 0.4330(15) 0.039(4) Uiso 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O2 C13 2 . 121.84(12) ?
C7 N1 C6 . . 125.64(9) ?
C7 N1 H1N . . 116.5(10) ?
C6 N1 H1N . . 117.6(10) ?
C2 C1 C6 . . 120.13(11) ?
C2 C1 H1 . . 119.9 ?
C6 C1 H1 . . 119.9 ?
C3 C2 C1 . . 120.18(11) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 119.82(11) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.16(12) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 119.98(11) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C1 . . 119.73(10) ?
C5 C6 N1 . . 121.13(10) ?
C1 C6 N1 . . 119.01(10) ?
N1 C7 C8 . . 121.02(10) ?
N1 C7 C12 . . 121.25(10) ?
C8 C7 C12 . . 117.72(10) ?
C9 C8 C7 . . 121.02(10) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 121.37(11) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C11 C10 C9 . . 118.80(11) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C10 C11 C12 . . 121.54(11) ?
C10 C11 H11 . . 119.2 ?
C12 C11 H11 . . 119.2 ?
C11 C12 C7 . . 119.53(10) ?
C11 C12 C13 . . 120.82(10) ?
C7 C12 C13 . . 119.62(10) ?
O1 C13 O2 . . 122.15(10) ?
O1 C13 C12 . . 126.76(10) ?
O2 C13 C12 . . 111.05(10) ?
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
O1 C13 . 1.2067(14) ?
O2 C13 2 1.3877(12) ?
O2 C13 . 1.3877(12) ?
N1 C7 . 1.3708(15) ?
N1 C6 . 1.4159(14) ?
N1 H1N . 0.903(16) ?
C1 C2 . 1.3853(18) ?
C1 C6 . 1.3880(16) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.3838(19) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3860(18) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3881(16) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3876(17) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.4109(15) ?
C7 C12 . 1.4199(15) ?
C8 C9 . 1.3708(17) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.3936(17) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3728(16) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.4047(15) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.4610(15) ?
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
N1 H1N O1 . 0.903(16) 1.966(15) 2.6629(14) 132.7(13)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.43(18) ?
C1 C2 C3 C4 . . . . 0.82(18) ?
C2 C3 C4 C5 . . . . -0.28(18) ?
C3 C4 C5 C6 . . . . -0.66(17) ?
C4 C5 C6 C1 . . . . 1.05(16) ?
C4 C5 C6 N1 . . . . 176.88(10) ?
C2 C1 C6 C5 . . . . -0.51(17) ?
C2 C1 C6 N1 . . . . -176.42(10) ?
C7 N1 C6 C5 . . . . 56.75(16) ?
C7 N1 C6 C1 . . . . -127.39(12) ?
C6 N1 C7 C8 . . . . 9.20(17) ?
C6 N1 C7 C12 . . . . -172.07(10) ?
N1 C7 C8 C9 . . . . 178.37(10) ?
C12 C7 C8 C9 . . . . -0.41(17) ?
C7 C8 C9 C10 . . . . 0.58(18) ?
C8 C9 C10 C11 . . . . -0.18(18) ?
C9 C10 C11 C12 . . . . -0.38(17) ?
C10 C11 C12 C7 . . . . 0.54(17) ?
C10 C11 C12 C13 . . . . -177.48(11) ?
N1 C7 C12 C11 . . . . -178.92(10) ?
C8 C7 C12 C11 . . . . -0.14(16) ?
N1 C7 C12 C13 . . . . -0.87(16) ?
C8 C7 C12 C13 . . . . 177.90(10) ?
C13 O2 C13 O1 2 . . . 18.14(8) ?
C13 O2 C13 C12 2 . . . -164.03(10) ?
C11 C12 C13 O1 . . . . 172.29(11) ?
C7 C12 C13 O1 . . . . -5.73(18) ?
C11 C12 C13 O2 . . . . -5.43(14) ?
C7 C12 C13 O2 . . . . 176.56(9) ?
