#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/33/2233333.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_2233333
loop_
_publ_author_name
'Maamri, Khalil'
'Zouihri, Hafid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 5-Bromo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-2,3-dione
;
_journal_coeditor_code           XU5413
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o240
_journal_paper_doi               10.1107/S160053681105447X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H8 Br N O2'
_chemical_formula_sum            'C11 H8 Br N O2'
_chemical_formula_weight         266.09
_chemical_name_systematic
;
5-Bromo-1-(prop-2-en-1-yl)-2,3-dihydro-1H-indole-2,3-dione
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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            8
_cell_length_a                   31.3411(5)
_cell_length_b                   7.89950(10)
_cell_length_c                   8.27160(10)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.7249
_cell_measurement_theta_min      2.5995
_cell_volume                     2047.87(5)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω 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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            50850
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.991
_exptl_absorpt_correction_T_max  0.6250
_exptl_absorpt_correction_T_min  0.5502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.634
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+1.4798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                2345
_reflns_number_total             2983
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5413.cif
_cod_data_source_block           I
_cod_database_code               2233333
_cod_database_fobs_code          2233333
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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_symmetry_multiplicity
Br Br1 0.241206(6) 0.49599(3) 0.59089(3) 0.03615(9) Uani d . 1 1
O O1 0.12709(5) 0.94850(17) 0.22127(18) 0.0334(3) Uani d . 1 1
O O2 0.06568(4) 0.77943(19) 0.00288(18) 0.0360(3) Uani d . 1 1
N N1 0.09810(5) 0.5408(2) 0.10576(18) 0.0237(3) Uani d . 1 1
C C1 0.13156(5) 0.5079(2) 0.2140(2) 0.0204(3) Uani d . 1 1
C C2 0.14721(6) 0.3526(2) 0.2635(2) 0.0253(3) Uani d . 1 1
H H2 0.1358 0.2520 0.2242 0.030 Uiso calc R 1 1
C C3 0.18068(6) 0.3522(2) 0.3744(2) 0.0270(4) Uani d . 1 1
H H3 0.1919 0.2497 0.4098 0.032 Uiso calc R 1 1
C C4 0.19752(6) 0.5033(2) 0.4327(2) 0.0250(3) Uani d . 1 1
C C5 0.18246(5) 0.6597(2) 0.3816(2) 0.0229(3) Uani d . 1 1
H H5 0.1943 0.7602 0.4192 0.027 Uiso calc R 1 1
C C6 0.14914(5) 0.6589(2) 0.2724(2) 0.0200(3) Uani d . 1 1
C C7 0.12453(5) 0.7978(2) 0.2011(2) 0.0229(3) Uani d . 1 1
C C8 0.09146(5) 0.7101(2) 0.0887(2) 0.0256(4) Uani d . 1 1
C C9 0.07183(6) 0.4118(2) 0.0275(2) 0.0295(4) Uani d . 1 1
H H9A 0.0894 0.3138 0.0044 0.035 Uiso calc R 1 1
H H9B 0.0615 0.4560 -0.0748 0.035 Uiso calc R 1 1
C C10 0.03449(6) 0.3572(3) 0.1269(3) 0.0342(4) Uani d . 1 1
H H10 0.0177 0.2706 0.0850 0.041 Uiso calc R 1 1
C C11 0.02314(7) 0.4189(3) 0.2666(3) 0.0379(5) Uani d . 1 1
H H11A 0.0389 0.5057 0.3135 0.046 Uiso calc R 1 1
H H11B -0.0008 0.3762 0.3193 0.046 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.02822(13) 0.04590(15) 0.03435(13) 0.00097(8) -0.00721(7) 0.00370(8)
O1 0.0391(8) 0.0187(6) 0.0424(8) 0.0006(6) 0.0109(6) 0.0018(6)
O2 0.0273(6) 0.0407(8) 0.0400(8) 0.0049(6) -0.0013(6) 0.0119(6)
N1 0.0215(7) 0.0233(7) 0.0264(7) -0.0038(6) -0.0012(6) -0.0004(6)
C1 0.0190(7) 0.0200(7) 0.0223(7) -0.0026(6) 0.0031(6) -0.0009(6)
C2 0.0287(9) 0.0173(7) 0.0300(9) -0.0020(6) 0.0035(7) -0.0015(6)
C3 0.0280(8) 0.0237(8) 0.0292(8) 0.0033(7) 0.0042(7) 0.0033(7)
C4 0.0205(7) 0.0303(9) 0.0240(8) -0.0001(6) 0.0014(6) 0.0017(7)
C5 0.0215(7) 0.0233(8) 0.0238(8) -0.0034(6) 0.0037(6) -0.0021(6)
C6 0.0191(7) 0.0167(7) 0.0241(8) -0.0021(6) 0.0054(6) -0.0009(6)
C7 0.0233(8) 0.0193(7) 0.0261(8) -0.0006(6) 0.0087(6) 0.0013(6)
C8 0.0203(7) 0.0282(8) 0.0283(9) -0.0002(6) 0.0059(6) 0.0041(7)
C9 0.0274(9) 0.0330(9) 0.0280(9) -0.0077(7) -0.0016(7) -0.0066(7)
C10 0.0303(9) 0.0370(10) 0.0353(10) -0.0142(8) -0.0030(8) -0.0007(8)
C11 0.0307(10) 0.0483(13) 0.0348(10) -0.0133(9) 0.0031(8) 0.0024(9)
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'
Br Br -0.2901 2.4595 '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
C8 N1 C1 111.23(14)
C8 N1 C9 123.58(16)
C1 N1 C9 125.10(15)
C2 C1 C6 120.94(16)
C2 C1 N1 128.18(15)
C6 C1 N1 110.88(14)
C1 C2 C3 117.64(16)
C1 C2 H2 121.2
C3 C2 H2 121.2
C2 C3 C4 120.78(17)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 121.93(17)
C5 C4 Br1 118.89(13)
C3 C4 Br1 119.16(13)
C6 C5 C4 116.90(16)
C6 C5 H5 121.5
C4 C5 H5 121.5
C5 C6 C1 121.79(15)
C5 C6 C7 131.16(15)
C1 C6 C7 107.00(15)
O1 C7 C6 130.50(18)
O1 C7 C8 124.55(17)
C6 C7 C8 104.94(14)
O2 C8 N1 127.52(18)
O2 C8 C7 126.57(17)
N1 C8 C7 105.90(15)
N1 C9 C10 113.51(16)
N1 C9 H9A 108.9
C10 C9 H9A 108.9
N1 C9 H9B 108.9
C10 C9 H9B 108.9
H9A C9 H9B 107.7
C11 C10 C9 126.42(19)
C11 C10 H10 116.8
C9 C10 H10 116.8
C10 C11 H11A 120.0
C10 C11 H11B 120.0
H11A C11 H11B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.8950(19)
O1 C7 1.205(2)
O2 C8 1.207(2)
N1 C8 1.361(2)
N1 C1 1.403(2)
N1 C9 1.461(2)
C1 C2 1.383(2)
C1 C6 1.400(2)
C2 C3 1.393(3)
C2 H2 0.9300
C3 C4 1.392(3)
C3 H3 0.9300
C4 C5 1.388(2)
C5 C6 1.381(2)
C5 H5 0.9300
C6 C7 1.465(2)
C7 C8 1.555(3)
C9 C10 1.494(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.304(3)
C10 H10 0.9300
C11 H11A 0.9300
C11 H11B 0.9300
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
C2 H2 O1 1_545 0.93 2.41 3.273(2) 154
C11 H11A O2 7_576 0.93 2.46 3.358(3) 163
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
C8 N1 C1 C2 179.10(18)
C9 N1 C1 C2 2.4(3)
C8 N1 C1 C6 -0.8(2)
C9 N1 C1 C6 -177.57(16)
C6 C1 C2 C3 0.6(3)
N1 C1 C2 C3 -179.32(17)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -1.1(3)
C2 C3 C4 Br1 177.05(14)
C3 C4 C5 C6 1.4(3)
Br1 C4 C5 C6 -176.78(12)
C4 C5 C6 C1 -0.7(2)
C4 C5 C6 C7 176.46(17)
C2 C1 C6 C5 -0.3(3)
N1 C1 C6 C5 179.64(15)
C2 C1 C6 C7 -178.08(16)
N1 C1 C6 C7 1.88(19)
C5 C6 C7 O1 -0.6(3)
C1 C6 C7 O1 176.84(19)
C5 C6 C7 C8 -179.54(17)
C1 C6 C7 C8 -2.06(17)
C1 N1 C8 O2 178.62(17)
C9 N1 C8 O2 -4.6(3)
C1 N1 C8 C7 -0.51(19)
C9 N1 C8 C7 176.28(15)
O1 C7 C8 O2 3.5(3)
C6 C7 C8 O2 -177.56(17)
O1 C7 C8 N1 -177.40(17)
C6 C7 C8 N1 1.59(18)
C8 N1 C9 C10 -90.0(2)
C1 N1 C9 C10 86.3(2)
N1 C9 C10 C11 3.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1619310
