#------------------------------------------------------------------------------
#$Date: 2016-04-16 04:58:09 +0300 (Sat, 16 Apr 2016) $
#$Revision: 182165 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/31/1543132.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_1543132
loop_
_publ_author_name
'Qachchachi, Fatima Zahrae'
'Kandri Rodi, Youssef'
'Haoudi, Amal'
'Essassi, El Mokhtar'
'Capet, Frédéric'
'Zouihri, Hafid'
_publ_section_title
;
 1-(3-Bromopropyl)indoline-2,3-dione
;
_journal_coeditor_code           HB4036
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x160593
_journal_paper_doi               10.1107/S2414314616005939
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C11 H10 Br N O2'
_chemical_formula_moiety         'C11 H10 Br N O2'
_chemical_formula_sum            'C11 H10 Br N O2'
_chemical_formula_weight         268.11
_chemical_name_systematic
;
1-(3-Bromopropyl)indoline-2,3-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.8300(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7113(2)
_cell_length_b                   8.1375(2)
_cell_length_c                   17.8089(4)
_cell_measurement_reflns_used    9592
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.63
_cell_measurement_theta_min      2.29
_cell_volume                     1115.03(5)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39739
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.516
_diffrn_reflns_theta_min         2.647
_exptl_absorpt_coefficient_mu    3.665
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       'irregular parallelepiped'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.238
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.988
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0547
_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)+(0.0638P)²+1.1939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                2360
_reflns_number_total             3393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4036sup1.cif
_cod_data_source_block           I
_cod_database_code               1543132
_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.
;
_shelx_estimated_absorpt_t_min   0.330
_shelx_estimated_absorpt_t_max   0.476
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
Br Br1 -0.05853(6) 0.49061(6) 0.36531(3) 0.0874(2) Uani d 1
C C1 0.5157(3) 0.7542(3) 0.46085(14) 0.0360(5) Uani d 1
C C2 0.4168(4) 0.7039(4) 0.51842(16) 0.0465(6) Uani d 1
H H2 0.3145 0.6446 0.5088 0.056 Uiso calc 1
C C3 0.4765(4) 0.7455(4) 0.59154(16) 0.0529(7) Uani d 1
H H3 0.4116 0.7138 0.6313 0.063 Uiso calc 1
C C4 0.6279(5) 0.8318(4) 0.60698(15) 0.0527(7) Uani d 1
H H4 0.6640 0.8567 0.6565 0.063 Uiso calc 1
C C5 0.7270(4) 0.8819(4) 0.54906(15) 0.0455(6) Uani d 1
H H5 0.8302 0.9394 0.5590 0.055 Uiso calc 1
C C6 0.6679(3) 0.8439(3) 0.47589(13) 0.0367(5) Uani d 1
C C7 0.7371(3) 0.8840(3) 0.40349(15) 0.0417(5) Uani d 1
C C8 0.6087(4) 0.8045(4) 0.34400(14) 0.0441(6) Uani d 1
C C9 0.3438(4) 0.6304(4) 0.34693(17) 0.0476(6) Uani d 1
H H9A 0.3108 0.5462 0.3818 0.057 Uiso calc 1
H H9B 0.3845 0.5760 0.3029 0.057 Uiso calc 1
C C10 0.1865(4) 0.7331(4) 0.32359(18) 0.0503(7) Uani d 1
H H10B 0.2184 0.8142 0.2871 0.060 Uiso calc 1
H H10A 0.1492 0.7914 0.3672 0.060 Uiso calc 1
C C11 0.0372(4) 0.6315(5) 0.28988(18) 0.0600(8) Uani d 1
H H11B 0.0772 0.5641 0.2496 0.072 Uiso calc 1
H H11A -0.0532 0.7038 0.2686 0.072 Uiso calc 1
N N1 0.4849(3) 0.7280(3) 0.38246(12) 0.0410(5) Uani d 1
O O1 0.8630(3) 0.9615(3) 0.38866(13) 0.0589(6) Uani d 1
O O2 0.6181(3) 0.8085(3) 0.27643(11) 0.0638(6) Uani 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'
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
C2 C1 C6 120.9(2)
C2 C1 N1 128.5(2)
C6 C1 N1 110.6(2)
C1 C2 C3 117.2(3)
C1 C2 H2 121.4
C3 C2 H2 121.4
C4 C3 C2 122.3(3)
C4 C3 H3 118.9
C2 C3 H3 118.9
C3 C4 C5 120.3(3)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 118.1(3)
C4 C5 H5 120.9
C6 C5 H5 120.9
C5 C6 C1 121.1(2)
C5 C6 C7 131.4(2)
C1 C6 C7 107.4(2)
O1 C7 C6 131.1(3)
O1 C7 C8 124.0(2)
C6 C7 C8 104.9(2)
O2 C8 N1 127.0(3)
O2 C8 C7 126.4(3)
N1 C8 C7 106.6(2)
N1 C9 C10 112.4(2)
N1 C9 H9A 109.1
C10 C9 H9A 109.1
N1 C9 H9B 109.1
C10 C9 H9B 109.1
H9A C9 H9B 107.9
C9 C10 C11 112.6(3)
C9 C10 H10B 109.1
C11 C10 H10B 109.1
C9 C10 H10A 109.1
C11 C10 H10A 109.1
H10B C10 H10A 107.8
C10 C11 Br1 111.2(2)
C10 C11 H11B 109.4
Br1 C11 H11B 109.4
C10 C11 H11A 109.4
Br1 C11 H11A 109.4
H11B C11 H11A 108.0
C8 N1 C1 110.5(2)
C8 N1 C9 124.0(2)
C1 N1 C9 125.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 Br1 1.948(4)
C1 C2 1.380(4)
C1 C6 1.393(4)
C1 N1 1.417(3)
C2 C3 1.394(4)
C2 H2 0.9300
C3 C4 1.375(5)
C3 H3 0.9300
C4 C5 1.385(4)
C4 H4 0.9300
C5 C6 1.386(4)
C5 H5 0.9300
C6 C7 1.465(3)
C7 O1 1.202(3)
C7 C8 1.543(4)
C8 O2 1.211(3)
C8 N1 1.363(3)
C9 N1 1.457(3)
C9 C10 1.508(4)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.510(4)
C10 H10B 0.9700
C10 H10A 0.9700
C11 H11B 0.9700
C11 H11A 0.9700
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
C4 H4 O2 4_576 0.93 2.57 3.232(3) 129 yes
C9 H9B O2 2_645 0.97 2.59 3.444(4) 146 yes
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
C6 C1 C2 C3 -0.4(4)
N1 C1 C2 C3 179.8(3)
C1 C2 C3 C4 -0.5(4)
C2 C3 C4 C5 0.4(5)
C3 C4 C5 C6 0.6(4)
C4 C5 C6 C1 -1.6(4)
C4 C5 C6 C7 177.2(3)
C2 C1 C6 C5 1.6(4)
N1 C1 C6 C5 -178.6(2)
C2 C1 C6 C7 -177.5(2)
N1 C1 C6 C7 2.3(3)
C5 C6 C7 O1 -0.5(5)
C1 C6 C7 O1 178.5(3)
C5 C6 C7 C8 -179.9(3)
C1 C6 C7 C8 -0.9(3)
O1 C7 C8 O2 0.6(5)
C6 C7 C8 O2 -180.0(3)
O1 C7 C8 N1 179.8(3)
C6 C7 C8 N1 -0.7(3)
N1 C9 C10 C11 -177.5(3)
C9 C10 C11 Br1 68.1(3)
O2 C8 N1 C1 -178.6(3)
C7 C8 N1 C1 2.1(3)
O2 C8 N1 C9 2.6(5)
C7 C8 N1 C9 -176.7(2)
C2 C1 N1 C8 177.0(3)
C6 C1 N1 C8 -2.8(3)
C2 C1 N1 C9 -4.3(4)
C6 C1 N1 C9 175.9(2)
C10 C9 N1 C8 -88.0(3)
C10 C9 N1 C1 93.4(3)

_cod_database_fobs_code 1543132
