##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
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data_I
_database_code_depnum_ccdc_archive 'CCDC 1473515'
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2016-04-11
_journal_date_accepted     2016-04-12
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S241431461600609X
_journal_coeditor_code     SJ4024
_publ_contact_author_name     'Hafid Zouihri'
_publ_contact_author_address
;\
Laboratoire d'Ingénierie des Matériaux et d'Environnement: \
Modélisation et Application (LIMEMA), Ibn Tofail University, Kénitra,
Morocco
;
_publ_contact_author_email     'hafid.zouihri@gmail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '00212653108344'
_publ_section_title
;
1-Propyl-1H-indole-2,3-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Qachchachi, Fatima Zahrae' .
;
Laboratoire de Chimie Organique Appliquée-Chimie Appliquée,
Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah,
Fès,
Morocco
;
    'Kandri Rodi, Youssef' .
;
Laboratoire de Chimie Organique Appliquée-Chimie Appliquée,
Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah,
Fès,
Morocco
;
    'Haoudi, Amal' .
;
Laboratoire de Chimie Organique Appliquée-Chimie Appliquée,
Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah,
Fès,
Morocco
;
    'Essassi, El Mokhtar' .
;
Laboratoire de Chimie Organique Hétérocyclique,
Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014
Avenue Ibn Batouta, Rabat,
Morocco
;
    'Capet, Frédéric' .
;
Unité de Catalyse et de Chimie du Solide (UCCS), UMR 8181.
Ecole Nationale Supérieure de Chimie de Lille,
France
;
    'Zouihri, Hafid' .
;
Laboratoire d'Ingénierie des Matériaux et d'Environnement,
Modélisation et Application (LIMEMA), Ibn Tofail University, Kénitra,
Morocco
;
_publ_section_synopsis
;
In the title compound, the plane of the propyl group is arched over the almost
planar nine-membered fused-ring system [maximum deviation = 0.0202(17) Å] at
a dihedral angle of 71.97(17)°.
;
_chemical_name_systematic
;
1-Propyl-1H-indole-2,3-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H11 N O2'
_chemical_formula_sum     'C11 H11 N O2'
_chemical_formula_iupac     'C11 H11 N O2'
_chemical_formula_weight     189.21
_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     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     4.4666(2)
_cell_length_b     12.9169(6)
_cell_length_c     16.3857(8)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     945.37(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3897
_cell_measurement_theta_min     2.49
_cell_measurement_theta_max     30.48
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'parallelepiped'
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.329
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     400
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_shelx_estimated_absorpt_T_min     0.975
_shelx_estimated_absorpt_T_max     0.991
_exptl_absorpt_correction_T_min     0.6809
_exptl_absorpt_correction_T_max     0.7461
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'microfocus source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8372
_diffrn_reflns_av_R_equivalents     0.0256
_diffrn_reflns_theta_min     2.008
_diffrn_reflns_theta_max     30.504
_diffrn_reflns_theta_full     26.000
_diffrn_measured_fraction_theta_max     0.937
_diffrn_measured_fraction_theta_full     0.970
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     22
_refine_special_details     ?
_reflns_number_total     2720
_reflns_number_gt     2474
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0442
_refine_ls_R_factor_gt     0.0379
_refine_ls_wR_factor_gt     0.0856
_refine_ls_wR_factor_ref     0.0891
_refine_ls_goodness_of_fit_ref     1.255
_refine_ls_restrained_S_all     1.255
_refine_ls_number_reflns     2720
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0430P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.006
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.234
_refine_diff_density_min     -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 912 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     -0.5(5)
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'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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
    C C7 0.2074(4) 0.23633(14) 0.34207(9) 0.0167(3) Uani d 1 . .
    C C5 0.0195(4) 0.50779(14) 0.32062(10) 0.0161(3) Uani d 1 . .
    C C3 -0.2671(4) 0.44800(15) 0.43838(10) 0.0200(4) Uani d 1 . .
    C C8 0.3971(4) 0.26930(14) 0.26673(10) 0.0167(3) Uani d 1 . .
    C C1 0.0449(3) 0.32977(13) 0.36607(9) 0.0145(3) Uani d 1 . .
    C C9 0.4709(4) 0.43360(15) 0.18883(10) 0.0173(3) Uani d 1 . .
    C C10 0.2755(4) 0.44538(14) 0.11315(10) 0.0179(3) Uani d 1 . .
    C C6 0.1282(3) 0.40851(13) 0.31200(9) 0.0131(3) Uani d 1 . .
    C C4 -0.1806(4) 0.52562(14) 0.38456(10) 0.0194(4) Uani d 1 . .
    C C2 -0.1525(4) 0.34886(14) 0.42971(10) 0.0166(3) Uani d 1 . .
    C C11 0.2039(5) 0.34352(16) 0.07157(12) 0.0270(4) Uani d 1 . .
    N N1 0.3325(3) 0.37085(11) 0.25297(8) 0.0150(3) Uani d 1 . .
    O O1 0.2111(3) 0.15078(9) 0.37136(7) 0.0235(3) Uani d 1 . .
    O O2 0.5712(3) 0.21478(10) 0.22898(8) 0.0247(3) Uani d 1 . .
    H H2 -0.211(5) 0.2930(18) 0.4661(14) 0.030(6) Uiso d 1 . .
    H H3 -0.405(5) 0.4602(16) 0.4792(14) 0.029(5) Uiso d 1 . .
    H H4 -0.266(5) 0.5948(17) 0.3915(12) 0.022(5) Uiso d 1 . .
    H H5 0.075(4) 0.5642(16) 0.2856(13) 0.024(5) Uiso d 1 . .
    H H9A 0.666(4) 0.3964(15) 0.1758(12) 0.016(5) Uiso d 1 . .
    H H9B 0.517(4) 0.5007(15) 0.2124(11) 0.011(4) Uiso d 1 . .
    H H10B 0.093(5) 0.4815(16) 0.1264(12) 0.023(5) Uiso d 1 . .
    H H10A 0.391(4) 0.4923(16) 0.0746(12) 0.021(5) Uiso d 1 . .
    H H11A 0.084(6) 0.3542(16) 0.0226(15) 0.034(6) Uiso d 1 . .
    H H11B 0.387(6) 0.3080(19) 0.0530(15) 0.044(7) Uiso d 1 . .
    H H11C 0.084(5) 0.2976(17) 0.1088(15) 0.031(6) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C7 O1 . 1.205(2) ?
    C7 C1 . 1.462(2) ?
    C7 C8 . 1.557(2) ?
    C5 C6 . 1.379(2) ?
    C5 C4 . 1.396(2) ?
    C5 H5 . 0.96(2) ?
    C3 C2 . 1.386(3) ?
    C3 C4 . 1.390(3) ?
    C3 H3 . 0.92(2) ?
    C8 O2 . 1.218(2) ?
    C8 N1 . 1.362(2) ?
    C1 C2 . 1.388(2) ?
    C1 C6 . 1.399(2) ?
    C9 N1 . 1.464(2) ?
    C9 C10 . 1.524(2) ?
    C9 H9A . 1.02(2) ?
    C9 H9B . 0.971(19) ?
    C10 C11 . 1.516(3) ?
    C10 H10B . 0.96(2) ?
    C10 H10A . 1.02(2) ?
    C6 N1 . 1.416(2) ?
    C4 H4 . 0.98(2) ?
    C2 H2 . 0.97(2) ?
    C11 H11A . 0.97(2) ?
    C11 H11B . 0.98(3) ?
    C11 H11C . 1.01(2) ?
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
    O1 C7 C1 . . 131.04(16) ?
    O1 C7 C8 . . 124.02(16) ?
    C1 C7 C8 . . 104.93(14) ?
    C6 C5 C4 . . 117.12(16) ?
    C6 C5 H5 . . 123.6(12) ?
    C4 C5 H5 . . 119.3(12) ?
    C2 C3 C4 . . 119.91(16) ?
    C2 C3 H3 . . 118.6(13) ?
    C4 C3 H3 . . 121.5(13) ?
    O2 C8 N1 . . 127.46(16) ?
    O2 C8 C7 . . 126.30(16) ?
    N1 C8 C7 . . 106.23(13) ?
    C2 C1 C6 . . 121.04(16) ?
    C2 C1 C7 . . 131.62(16) ?
    C6 C1 C7 . . 107.31(14) ?
    N1 C9 C10 . . 113.42(13) ?
    N1 C9 H9A . . 104.5(11) ?
    C10 C9 H9A . . 111.5(11) ?
    N1 C9 H9B . . 107.3(11) ?
    C10 C9 H9B . . 110.8(11) ?
    H9A C9 H9B . . 108.9(15) ?
    C11 C10 C9 . . 113.57(15) ?
    C11 C10 H10B . . 110.1(12) ?
    C9 C10 H10B . . 110.4(12) ?
    C11 C10 H10A . . 110.2(12) ?
    C9 C10 H10A . . 106.0(11) ?
    H10B C10 H10A . . 106.2(17) ?
    C5 C6 C1 . . 121.17(15) ?
    C5 C6 N1 . . 128.07(14) ?
    C1 C6 N1 . . 110.75(14) ?
    C3 C4 C5 . . 122.35(17) ?
    C3 C4 H4 . . 118.5(12) ?
    C5 C4 H4 . . 119.2(12) ?
    C1 C2 C3 . . 118.41(16) ?
    C1 C2 H2 . . 119.9(13) ?
    C3 C2 H2 . . 121.7(13) ?
    C10 C11 H11A . . 111.3(12) ?
    C10 C11 H11B . . 111.7(14) ?
    H11A C11 H11B . . 105(2) ?
    C10 C11 H11C . . 110.6(13) ?
    H11A C11 H11C . . 106.9(19) ?
    H11B C11 H11C . . 110.7(19) ?
    C8 N1 C6 . . 110.75(13) ?
    C8 N1 C9 . . 124.24(14) ?
    C6 N1 C9 . . 124.91(14) ?
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
    O1 C7 C8 O2 . . . . -0.7(3) ?
    C1 C7 C8 O2 . . . . 178.18(16) ?
    O1 C7 C8 N1 . . . . -179.65(16) ?
    C1 C7 C8 N1 . . . . -0.79(17) ?
    O1 C7 C1 C2 . . . . 0.4(3) ?
    C8 C7 C1 C2 . . . . -178.34(16) ?
    O1 C7 C1 C6 . . . . 178.56(17) ?
    C8 C7 C1 C6 . . . . -0.18(17) ?
    N1 C9 C10 C11 . . . . -61.1(2) ?
    C4 C5 C6 C1 . . . . -1.1(2) ?
    C4 C5 C6 N1 . . . . -179.70(15) ?
    C2 C1 C6 C5 . . . . 0.7(2) ?
    C7 C1 C6 C5 . . . . -177.72(14) ?
    C2 C1 C6 N1 . . . . 179.48(14) ?
    C7 C1 C6 N1 . . . . 1.09(18) ?
    C2 C3 C4 C5 . . . . 0.3(3) ?
    C6 C5 C4 C3 . . . . 0.6(2) ?
    C6 C1 C2 C3 . . . . 0.3(2) ?
    C7 C1 C2 C3 . . . . 178.24(17) ?
    C4 C3 C2 C1 . . . . -0.8(2) ?
    O2 C8 N1 C6 . . . . -177.48(16) ?
    C7 C8 N1 C6 . . . . 1.48(16) ?
    O2 C8 N1 C9 . . . . -1.0(3) ?
    C7 C8 N1 C9 . . . . 177.95(13) ?
    C5 C6 N1 C8 . . . . 177.01(16) ?
    C1 C6 N1 C8 . . . . -1.69(17) ?
    C5 C6 N1 C9 . . . . 0.6(2) ?
    C1 C6 N1 C9 . . . . -178.13(14) ?
    C10 C9 N1 C8 . . . . 99.75(18) ?
    C10 C9 N1 C6 . . . . -84.27(19) ?
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
    C5 H5 O2 3_655 0.96(2) 2.52(2) 3.339(2) 143.6(16) yes
    C9 H9A O2 . 1.018(18) 2.538(19) 2.936(2) 102.8(12) yes
    C10 H10B O1 3_555 0.96(2) 2.57(2) 3.439(2) 149.4(17) yes
