#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/01/2240172.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_2240172
loop_
_publ_author_name
'Ezemobi, Fortune'
'North, Henry'
'Scott, Kenneth R.'
'Wutoh, Anthohy K.'
'Butcher, Ray J.'
_publ_section_title
;
 Crystal structures of 2-methoxyisoindoline-1,3-dione,
 1,3-dioxoisoindolin-2-yl methyl carbonate and
 1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl methyl carbonate:
 three anticonvulsant compounds
;
_journal_coeditor_code           SU2795
_journal_issue                   12
_journal_name_full
'Acta Crystallographica Section E Structure Reports Online'
_journal_page_first              456
_journal_paper_doi               10.1107/S1600536814023769
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C9 H7 N O3'
_chemical_formula_moiety         'C9 H7 N O3'
_chemical_formula_sum            'C9 H7 N O3'
_chemical_formula_weight         177.16
_chemical_name_systematic
;
2-Methoxyisoindoline-1,3-dione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2987(4)
_cell_length_b                   7.0243(10)
_cell_length_c                   27.587(4)
_cell_measurement_reflns_used    1634
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.0583
_cell_measurement_theta_min      3.2479
_cell_volume                     833.00(19)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'Agilent Xcalibur (Ruby, Gemini)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5145
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         31.135
_diffrn_reflns_theta_min         3.255
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.6575
_exptl_crystal_size_mid          0.2334
_exptl_crystal_size_min          0.0399
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0842P)²+1.0430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2209
_refine_ls_wR_factor_ref         0.2287
_reflns_number_gt                1989
_reflns_number_total             2259
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2795sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        832.98(19)
_cod_database_code               2240172
_cod_database_fobs_code          2240172
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_occupancy
O O1 0.6646(10) 0.6034(6) 0.30567(13) 0.0417(10) Uani d 1
O O2 0.6859(9) 0.0978(4) 0.41116(14) 0.0358(9) Uani d 1
O O3 0.9419(9) 0.2430(6) 0.32341(14) 0.0413(10) Uani d 1
N N1 0.7177(10) 0.3273(6) 0.35101(15) 0.0293(9) Uani d 1
C C1 0.6031(12) 0.5105(7) 0.34055(17) 0.0284(10) Uani d 1
C C2 0.3946(11) 0.5531(6) 0.38248(16) 0.0229(9) Uani d 1
C C3 0.2197(12) 0.7156(6) 0.39295(18) 0.0306(11) Uani d 1
H H3A 0.2110 0.8199 0.3711 0.037 Uiso calc 1
C C4 0.0601(13) 0.7184(6) 0.4364(2) 0.0318(11) Uani d 1
H H4A -0.0591 0.8278 0.4445 0.038 Uiso calc 1
C C5 0.0684(12) 0.5655(6) 0.46879(18) 0.0275(10) Uani d 1
H H5A -0.0436 0.5722 0.4984 0.033 Uiso calc 1
C C6 0.2410(10) 0.4030(6) 0.45760(16) 0.0250(9) Uani d 1
H H6A 0.2465 0.2977 0.4792 0.030 Uiso calc 1
C C7 0.4026(11) 0.3989(6) 0.41468(16) 0.0229(9) Uani d 1
C C8 0.6130(11) 0.2513(6) 0.39447(17) 0.0247(9) Uani d 1
C C9 0.8051(17) 0.1214(10) 0.2870(2) 0.0532(18) Uani d 1
H H9A 0.9693 0.0701 0.2661 0.080 Uiso calc 1
H H9B 0.6583 0.1952 0.2674 0.080 Uiso calc 1
H H9C 0.6948 0.0162 0.3028 0.080 Uiso calc 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
N1 O3 C9 110.9(4)
O3 N1 C8 123.0(4)
O3 N1 C1 122.0(4)
C8 N1 C1 114.5(4)
O1 C1 N1 126.0(5)
O1 C1 C2 130.4(5)
N1 C1 C2 103.6(4)
C3 C2 C7 120.9(4)
C3 C2 C1 130.3(4)
C7 C2 C1 108.7(4)
C4 C3 C2 117.3(4)
C4 C3 H3A 121.3
C2 C3 H3A 121.3
C3 C4 C5 122.1(4)
C3 C4 H4A 119.0
C5 C4 H4A 119.0
C6 C5 C4 120.0(5)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C7 C6 C5 118.5(4)
C7 C6 H6A 120.8
C5 C6 H6A 120.8
C6 C7 C2 121.2(4)
C6 C7 C8 130.3(4)
C2 C7 C8 108.5(4)
O2 C8 N1 125.9(4)
O2 C8 C7 129.4(5)
N1 C8 C7 104.7(4)
O3 C9 H9A 109.5
O3 C9 H9B 109.5
H9A C9 H9B 109.5
O3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.193(6)
O2 C8 1.214(5)
O3 N1 1.364(5)
O3 C9 1.444(7)
N1 C8 1.387(6)
N1 C1 1.407(6)
C1 C2 1.494(7)
C2 C3 1.397(6)
C2 C7 1.401(6)
C3 C4 1.381(8)
C3 H3A 0.9500
C4 C5 1.398(7)
C4 H4A 0.9500
C5 C6 1.396(6)
C5 H5A 0.9500
C6 C7 1.373(6)
C6 H6A 0.9500
C7 C8 1.484(6)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
C4 H4A O2 1_465 0.95 2.38 3.190(4) 143
C9 H9A O1 4_745 0.98 2.54 3.428(7) 151
C9 H9B O1 4_645 0.98 2.53 3.260(8) 131
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
C9 O3 N1 C8 93.4(6)
C9 O3 N1 C1 -94.8(6)
O3 N1 C1 O1 6.7(8)
C8 N1 C1 O1 179.1(5)
O3 N1 C1 C2 -173.7(4)
C8 N1 C1 C2 -1.2(5)
O1 C1 C2 C3 -1.7(9)
N1 C1 C2 C3 178.6(5)
O1 C1 C2 C7 -179.2(5)
N1 C1 C2 C7 1.1(5)
C7 C2 C3 C4 0.9(7)
C1 C2 C3 C4 -176.4(5)
C2 C3 C4 C5 -0.5(7)
C3 C4 C5 C6 -0.2(7)
C4 C5 C6 C7 0.7(7)
C5 C6 C7 C2 -0.4(7)
C5 C6 C7 C8 177.1(4)
C3 C2 C7 C6 -0.4(7)
C1 C2 C7 C6 177.4(4)
C3 C2 C7 C8 -178.4(4)
C1 C2 C7 C8 -0.6(5)
O3 N1 C8 O2 -6.2(7)
C1 N1 C8 O2 -178.5(4)
O3 N1 C8 C7 173.2(4)
C1 N1 C8 C7 0.9(5)
C6 C7 C8 O2 1.5(8)
C2 C7 C8 O2 179.2(5)
C6 C7 C8 N1 -177.9(5)
C2 C7 C8 N1 -0.1(5)
