##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-2013
_database_code_depnum_ccdc_archive     'CCDC 1036387'
_chemical_name_systematic
;
2-(1,3-Dioxoindan-2-yl)isoquinoline-1,3,4-trione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H9 N O5'
_chemical_formula_sum     'C18 H9 N O5'
_chemical_formula_iupac     'C18 H9 N O5'
_chemical_formula_weight     319.26
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,1/2+y,1/2-z
    3 -x,-y,-z
    4 x,1/2-y,1/2+z
_cell_length_a     12.60800(10)
_cell_length_b     13.6849(2)
_cell_length_c     8.44670(10)
_cell_angle_alpha     90
_cell_angle_beta     102.0510(10)
_cell_angle_gamma     90
_cell_volume     1425.27(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6347
_cell_measurement_theta_min     6.26
_cell_measurement_theta_max     71.73
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.239
_exptl_crystal_size_mid     0.146
_exptl_crystal_size_min     0.142
_exptl_crystal_density_diffrn     1.488
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.931
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_shelx_estimated_absorpt_T_min     0.808
_shelx_estimated_absorpt_T_max     0.879
_exptl_absorpt_correction_T_min     0.8081
_exptl_absorpt_correction_T_max     0.8792
_exptl_special_details     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9639
_diffrn_reflns_av_R_equivalents     0.0239
_diffrn_reflns_theta_min     6.258
_diffrn_reflns_theta_max     71.962
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.924
_diffrn_measured_fraction_theta_full     0.953
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     8
_refine_special_details     ?
_reflns_number_total     2597
_reflns_number_gt     2458
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0360
_refine_ls_R_factor_gt     0.0346
_refine_ls_wR_factor_gt     0.0922
_refine_ls_wR_factor_ref     0.0934
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     2597
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0504P)²+0.5485P]
where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.270
_refine_diff_density_min     -0.201
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.36681(7) 0.34686(7) -0.36897(11) 0.0226(2) Uani d 1 . .
    O O2 0.56844(7) 0.37737(7) -0.18918(11) 0.0244(2) Uani d 1 . .
    O O3 0.22076(7) 0.37449(6) 0.07501(11) 0.0212(2) Uani d 1 . .
    O O4 0.14773(7) 0.52030(7) -0.25876(13) 0.0310(3) Uani d 1 . .
    O O5 0.14677(7) 0.18880(6) -0.12358(10) 0.0208(2) Uani d 1 . .
    N N1 0.29330(8) 0.35524(7) -0.14517(12) 0.0167(2) Uani d 1 . .
    C C1 0.37928(9) 0.35678(8) -0.22453(15) 0.0171(3) Uani d 1 . .
    C C2 0.49378(10) 0.37240(8) -0.11979(15) 0.0182(3) Uani d 1 . .
    C C3 0.50578(10) 0.38012(8) 0.05673(15) 0.0173(3) Uani d 1 . .
    C C4 0.60836(10) 0.39054(9) 0.15659(16) 0.0202(3) Uani d 1 . .
    H H4A 0.6710 0.3933 0.1108 0.024 Uiso calc 1 . .
    C C5 0.61838(10) 0.39680(9) 0.32253(16) 0.0219(3) Uani d 1 . .
    H H5A 0.6880 0.4043 0.3907 0.026 Uiso calc 1 . .
    C C6 0.52631(10) 0.39207(9) 0.39026(16) 0.0213(3) Uani d 1 . .
    H H6A 0.5339 0.3947 0.5045 0.026 Uiso calc 1 . .
    C C7 0.42389(10) 0.38360(8) 0.29149(15) 0.0191(3) Uani d 1 . .
    H H7A 0.3614 0.3817 0.3377 0.023 Uiso calc 1 . .
    C C8 0.41329(10) 0.37786(8) 0.12429(15) 0.0172(3) Uani d 1 . .
    C C9 0.30286(10) 0.36955(8) 0.02176(15) 0.0172(3) Uani d 1 . .
    C C10 0.18389(9) 0.34521(9) -0.24087(15) 0.0180(3) Uani d 1 . .
    H H10A 0.1894 0.3278 -0.3539 0.022 Uiso calc 1 . .
    C C11 0.11456(10) 0.43817(9) -0.24898(16) 0.0210(3) Uani d 1 . .
    C C12 0.00327(10) 0.40620(9) -0.24322(16) 0.0215(3) Uani d 1 . .
    C C13 -0.09105(10) 0.46146(10) -0.26425(18) 0.0276(3) Uani d 1 . .
    H H13A -0.0910 0.5291 -0.2893 0.033 Uiso calc 1 . .
    C C14 -0.18531(11) 0.41422(10) -0.2473(2) 0.0314(3) Uani d 1 . .
    H H14A -0.2510 0.4502 -0.2610 0.038 Uiso calc 1 . .
    C C15 -0.18544(11) 0.31468(10) -0.21033(19) 0.0315(3) Uani d 1 . .
    H H15A -0.2513 0.2842 -0.2000 0.038 Uiso calc 1 . .
    C C16 -0.09097(11) 0.25943(10) -0.18845(18) 0.0267(3) Uani d 1 . .
    H H16A -0.0910 0.1918 -0.1629 0.032 Uiso calc 1 . .
    C C17 0.00336(10) 0.30685(9) -0.20540(15) 0.0201(3) Uani d 1 . .
    C C18 0.11462(9) 0.26700(8) -0.18079(14) 0.0173(3) Uani d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C1 . 1.2048(15) ?
    O2 C2 . 1.2102(15) ?
    O3 C9 . 1.2136(15) ?
    O4 C11 . 1.2080(16) ?
    O5 C18 . 1.2088(15) ?
    N1 C1 . 1.3886(15) ?
    N1 C9 . 1.4036(16) ?
    N1 C10 . 1.4525(15) ?
    C1 C2 . 1.5424(16) ?
    C2 C3 . 1.4707(17) ?
    C3 C4 . 1.3961(17) ?
    C3 C8 . 1.4016(17) ?
    C4 C5 . 1.3835(18) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.3987(18) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.3881(18) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.3927(18) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.4825(17) ?
    C10 C18 . 1.5332(16) ?
    C10 C11 . 1.5370(16) ?
    C10 H10A . 1.0000 ?
    C11 C12 . 1.4802(17) ?
    C12 C13 . 1.3890(18) ?
    C12 C17 . 1.3966(17) ?
    C13 C14 . 1.3863(19) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.398(2) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.3901(19) ?
    C15 H15A . 0.9500 ?
    C16 C17 . 1.3883(18) ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.4787(16) ?
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
    C1 N1 C9 . . 124.81(10) ?
    C1 N1 C10 . . 118.64(10) ?
    C9 N1 C10 . . 116.40(10) ?
    O1 C1 N1 . . 122.48(11) ?
    O1 C1 C2 . . 120.34(11) ?
    N1 C1 C2 . . 117.17(10) ?
    O2 C2 C3 . . 124.14(11) ?
    O2 C2 C1 . . 117.35(11) ?
    C3 C2 C1 . . 118.51(10) ?
    C4 C3 C8 . . 120.06(11) ?
    C4 C3 C2 . . 120.40(11) ?
    C8 C3 C2 . . 119.54(11) ?
    C5 C4 C3 . . 119.71(11) ?
    C5 C4 H4A . . 120.1 ?
    C3 C4 H4A . . 120.1 ?
    C4 C5 C6 . . 120.23(11) ?
    C4 C5 H5A . . 119.9 ?
    C6 C5 H5A . . 119.9 ?
    C7 C6 C5 . . 120.36(12) ?
    C7 C6 H6A . . 119.8 ?
    C5 C6 H6A . . 119.8 ?
    C6 C7 C8 . . 119.63(11) ?
    C6 C7 H7A . . 120.2 ?
    C8 C7 H7A . . 120.2 ?
    C7 C8 C3 . . 119.98(11) ?
    C7 C8 C9 . . 118.45(11) ?
    C3 C8 C9 . . 121.57(11) ?
    O3 C9 N1 . . 118.63(11) ?
    O3 C9 C8 . . 123.28(11) ?
    N1 C9 C8 . . 118.09(10) ?
    N1 C10 C18 . . 114.97(10) ?
    N1 C10 C11 . . 114.32(10) ?
    C18 C10 C11 . . 103.57(9) ?
    N1 C10 H10A . . 107.9 ?
    C18 C10 H10A . . 107.9 ?
    C11 C10 H10A . . 107.9 ?
    O4 C11 C12 . . 128.41(12) ?
    O4 C11 C10 . . 124.84(11) ?
    C12 C11 C10 . . 106.74(10) ?
    C13 C12 C17 . . 121.27(12) ?
    C13 C12 C11 . . 128.83(12) ?
    C17 C12 C11 . . 109.86(11) ?
    C14 C13 C12 . . 117.55(12) ?
    C14 C13 H13A . . 121.2 ?
    C12 C13 H13A . . 121.2 ?
    C13 C14 C15 . . 121.24(12) ?
    C13 C14 H14A . . 119.4 ?
    C15 C14 H14A . . 119.4 ?
    C16 C15 C14 . . 121.26(12) ?
    C16 C15 H15A . . 119.4 ?
    C14 C15 H15A . . 119.4 ?
    C17 C16 C15 . . 117.44(12) ?
    C17 C16 H16A . . 121.3 ?
    C15 C16 H16A . . 121.3 ?
    C16 C17 C12 . . 121.25(11) ?
    C16 C17 C18 . . 128.40(11) ?
    C12 C17 C18 . . 110.28(10) ?
    O5 C18 C17 . . 127.71(11) ?
    O5 C18 C10 . . 125.71(11) ?
    C17 C18 C10 . . 106.57(10) ?
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
    C9 N1 C1 O1 . . . . -177.84(11) ?
    C10 N1 C1 O1 . . . . -2.54(16) ?
    C9 N1 C1 C2 . . . . 1.89(16) ?
    C10 N1 C1 C2 . . . . 177.19(9) ?
    O1 C1 C2 O2 . . . . 2.38(17) ?
    N1 C1 C2 O2 . . . . -177.36(10) ?
    O1 C1 C2 C3 . . . . -177.50(11) ?
    N1 C1 C2 C3 . . . . 2.76(15) ?
    O2 C2 C3 C4 . . . . -2.32(18) ?
    C1 C2 C3 C4 . . . . 177.55(10) ?
    O2 C2 C3 C8 . . . . 177.08(11) ?
    C1 C2 C3 C8 . . . . -3.05(16) ?
    C8 C3 C4 C5 . . . . 1.19(17) ?
    C2 C3 C4 C5 . . . . -179.41(11) ?
    C3 C4 C5 C6 . . . . 0.42(18) ?
    C4 C5 C6 C7 . . . . -1.67(19) ?
    C5 C6 C7 C8 . . . . 1.27(18) ?
    C6 C7 C8 C3 . . . . 0.35(17) ?
    C6 C7 C8 C9 . . . . -179.58(10) ?
    C4 C3 C8 C7 . . . . -1.59(17) ?
    C2 C3 C8 C7 . . . . 179.01(10) ?
    C4 C3 C8 C9 . . . . 178.35(10) ?
    C2 C3 C8 C9 . . . . -1.06(16) ?
    C1 N1 C9 O3 . . . . 174.03(10) ?
    C10 N1 C9 O3 . . . . -1.36(15) ?
    C1 N1 C9 C8 . . . . -5.98(16) ?
    C10 N1 C9 C8 . . . . 178.63(10) ?
    C7 C8 C9 O3 . . . . 5.45(17) ?
    C3 C8 C9 O3 . . . . -174.48(11) ?
    C7 C8 C9 N1 . . . . -174.54(10) ?
    C3 C8 C9 N1 . . . . 5.52(16) ?
    C1 N1 C10 C18 . . . . 131.20(11) ?
    C9 N1 C10 C18 . . . . -53.10(13) ?
    C1 N1 C10 C11 . . . . -109.16(12) ?
    C9 N1 C10 C11 . . . . 66.53(13) ?
    N1 C10 C11 O4 . . . . 38.25(18) ?
    C18 C10 C11 O4 . . . . 164.10(13) ?
    N1 C10 C11 C12 . . . . -142.00(11) ?
    C18 C10 C11 C12 . . . . -16.15(13) ?
    O4 C11 C12 C13 . . . . 7.3(2) ?
    C10 C11 C12 C13 . . . . -172.42(13) ?
    O4 C11 C12 C17 . . . . -170.35(14) ?
    C10 C11 C12 C17 . . . . 9.92(14) ?
    C17 C12 C13 C14 . . . . -0.4(2) ?
    C11 C12 C13 C14 . . . . -177.81(14) ?
    C12 C13 C14 C15 . . . . 0.0(2) ?
    C13 C14 C15 C16 . . . . 0.3(2) ?
    C14 C15 C16 C17 . . . . -0.3(2) ?
    C15 C16 C17 C12 . . . . -0.1(2) ?
    C15 C16 C17 C18 . . . . 176.66(13) ?
    C13 C12 C17 C16 . . . . 0.4(2) ?
    C11 C12 C17 C16 . . . . 178.31(12) ?
    C13 C12 C17 C18 . . . . -176.86(12) ?
    C11 C12 C17 C18 . . . . 1.01(15) ?
    C16 C17 C18 O5 . . . . -9.2(2) ?
    C12 C17 C18 O5 . . . . 167.87(12) ?
    C16 C17 C18 C10 . . . . 171.40(13) ?
    C12 C17 C18 C10 . . . . -11.55(14) ?
    N1 C10 C18 O5 . . . . -37.31(17) ?
    C11 C10 C18 O5 . . . . -162.74(12) ?
    N1 C10 C18 C17 . . . . 142.12(10) ?
    C11 C10 C18 C17 . . . . 16.70(12) ?
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
    _geom_hbond_publ_flag
    C6 H6A O2 1_556 0.9500 2.5400 3.4862(16) 171.00 yes
    C7 H7A O1 1_556 0.9500 2.5100 3.1397(15) 124.00 yes
    C10 H10A O5 4_554 1.0000 2.2400 3.2022(15) 161.00 yes
    C13 H13A O5 2_554 0.9500 2.3700 3.2852(16) 163.00 yes
    C16 H16A O4 2_544 0.9500 2.5000 3.3596(17) 150.00 yes
_shelxl_version_number       20.13
data_New_Global_Publ_Block
_journal_date_recd_electronic     2014-10-30
_journal_date_accepted     2014-11-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      1
_journal_page_first     o6
_journal_page_last     o7
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989014025997
_journal_coeditor_code     ZL2607
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Hoong-Kun Fun'
;
Department of Pharmaceutical Chemistry
College of Pharmacy
King Saud University
PO Box 2457
Riaydh 11451
Saudi Arabia
;
 hfun.c@ksu.edu.sa
    'Raza Murad Ghalib'
;
Department of Chemistry
Faculty of Sciences & Arts Khulais
King Abdulaziz University
Jeddah
KSA
;
 raza2005communications@gmail.com
_publ_contact_author_fax     '+966 146-76220'
_publ_contact_author_phone     '+966 146-77335'
_publ_section_title
;
Crystal structure of 2-(1,3-dioxoindan-2-yl)isoquinoline-1,3,4-trione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Raza Murad Ghalib' .
;
Department of Chemistry,
Faculty of Sciences & Arts Khulais,
King Abdulaziz University, Jeddah, KSA
;
    'Chidan Kumar, C. S.'
;
Thomson Reuters ResearcherID: C-3194-2011.
;
;
X-ray Crystallography Unit,
School of Physics,
Universiti Sains Malaysia,
11800 USM, Penang,
Malaysia
Department of Chemistry
Alva's Institute of Engineering & Technology
Mijar, Moodbidri 574 225
Karnataka, India
;
    'Rokiah Hashim' .
;
School of Industrial Technology,
Universiti Sains Malaysia,
11800 USM, Penang,
Malaysia
;
    'Othman Sulaiman' .
;
School of Industrial Technology,
Universiti Sains Malaysia,
11800 USM, Penang,
Malaysia
;
    'Hoong-Kun Fun'
;
Thomson Reuters ResearcherID: A-3561-2009.
;
;
Department of Pharmaceutical Chemistry,
College of Pharmacy,
King Saud University,
PO Box 2457, Riaydh 11451,
Saudi Arabia
X-ray Crystallography Unit,
School of Physics,
Universiti Sains Malaysia,
11800 USM, Penang,
Malaysia
;
