#------------------------------------------------------------------------------
#$Date: 2017-07-12 15:28:44 +0300 (Wed, 12 Jul 2017) $
#$Revision: 198673 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520459.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520459
loop_
_publ_author_name
'Onyeabo, Romanus O.'
'Edwards, Mark'
'Spencer, John'
'Tizzard, Graham J.'
'Coles, Simon J.'
_publ_section_title
;
 Bromo Oxindole
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1323
_journal_year                    2010
_chemical_formula_moiety         'C15 H10 Br N O, H2 O'
_chemical_formula_sum            'C15 H12 Br N O2'
_chemical_formula_weight         318.17
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.698(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.623(3)
_cell_length_b                   4.0710(5)
_cell_length_c                   32.979(4)
_cell_measurement_reflns_used    25615
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2579.8(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics
'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 66.065
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_sigmaI/netI    0.0842
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            9093
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.183
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_correction_T_min  0.7414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+56.6839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                2064
_reflns_number_total             2888
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-1323.cif
_cod_data_source_block           2010src0792ra
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-07-12

Citation :
Onyeabo, Romanus O and Edwards, Mark and Spencer, John and 
Tizzard, Graham J and Coles, Simon J (2010) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1323)

More at:
http://ecrystals.chem.soton.ac.uk/1323/
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1520459
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.2771(4) -0.5058(18) 0.45224(19) 0.0247(16) Uani 1 1 d . . . 0
C2 C 0.2785(4) -0.3241(19) 0.41293(19) 0.0236(14) Uani 1 1 d . . . 0
C3 C 0.2090(3) -0.1948(18) 0.39907(19) 0.0227(14) Uani 1 1 d . . . 0
C4 C 0.1755(4) 0.0037(17) 0.3660(2) 0.0245(16) Uani 1 1 d . . . 0
H4 H 0.2002 0.0756 0.3456 0.029 Uiso 1 1 calc R . . 0
C5 C 0.1064(4) 0.0944(18) 0.3631(2) 0.0277(16) Uani 1 1 d . . . 0
H5 H 0.0843 0.2284 0.3407 0.033 Uiso 1 1 calc R . . 0
C6 C 0.0691(4) -0.0080(19) 0.3925(2) 0.0288(17) Uani 1 1 d . . . 0
H6 H 0.0215 0.0506 0.3895 0.035 Uiso 1 1 calc R . . 0
C7 C 0.1013(4) -0.196(2) 0.4263(2) 0.0282(16) Uani 1 1 d . . . 0
H7 H 0.0769 -0.2588 0.4472 0.034 Uiso 1 1 calc R . . 0
C8 C 0.1699(3) -0.2880(17) 0.42859(18) 0.0214(14) Uani 1 1 d . . . 0
C9 C 0.3394(4) -0.3067(18) 0.3994(2) 0.0253(15) Uani 1 1 d . . . 0
H9 H 0.3796 -0.3886 0.4177 0.030 Uiso 1 1 calc R . . 0
C10 C 0.3502(4) -0.1743(19) 0.35931(19) 0.0246(15) Uani 1 1 d . . . 0
C11 C 0.3037(4) -0.2445(17) 0.3227(2) 0.0255(16) Uani 1 1 d . . . 0
H11 H 0.2626 -0.3656 0.3235 0.031 Uiso 1 1 calc R . . 0
C12 C 0.3166(4) -0.1394(17) 0.28476(19) 0.0244(15) Uani 1 1 d . . . 0
H12 H 0.2849 -0.1875 0.2597 0.029 Uiso 1 1 calc R . . 0
C13 C 0.3770(4) 0.0373(18) 0.2846(2) 0.0250(16) Uani 1 1 d . . . 0
C14 C 0.4253(4) 0.1065(18) 0.3205(2) 0.0269(16) Uani 1 1 d . . . 0
H14 H 0.4666 0.2252 0.3196 0.032 Uiso 1 1 calc R . . 0
C15 C 0.4113(4) -0.0033(19) 0.3581(2) 0.0283(17) Uani 1 1 d . . . 0
H15 H 0.4438 0.0389 0.3831 0.034 Uiso 1 1 calc R . . 0
N1 N 0.2114(3) -0.4743(15) 0.45970(16) 0.0249(13) Uani 1 1 d . . . 0
H1 H 0.1972 -0.5594 0.4811 0.030 Uiso 1 1 calc R . . 0
O1 O 0.3249(3) -0.6564(14) 0.47460(13) 0.0303(12) Uani 1 1 d . . . 0
Br1 Br 0.39394(4) 0.1889(2) 0.23279(2) 0.0310(2) Uani 1 1 d . . . 0
O1W1 O 0.4676(4) -0.746(3) 0.4773(2) 0.103(4) Uani 1 1 d . . . 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 N1 124.7(6) . .
O1 C1 C2 128.2(6) . .
N1 C1 C2 107.0(6) . .
C9 C2 C3 135.4(7) . .
C9 C2 C1 118.7(7) . .
C3 C2 C1 105.8(5) . .
C8 C3 C4 117.1(6) . .
C8 C3 C2 107.1(6) . .
C4 C3 C2 135.7(6) . .
C5 C4 C3 120.1(6) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C4 C5 C6 121.1(7) . .
C4 C5 H5 119.5 . .
C6 C5 H5 119.5 . .
C7 C6 C5 120.3(7) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C8 C7 C6 118.0(6) . .
C8 C7 H7 121.0 . .
C6 C7 H7 121.0 . .
C7 C8 N1 127.0(6) . .
C7 C8 C3 123.3(6) . .
N1 C8 C3 109.7(6) . .
C2 C9 C10 127.2(7) . .
C2 C9 H9 116.4 . .
C10 C9 H9 116.4 . .
C11 C10 C15 119.6(6) . .
C11 C10 C9 121.0(7) . .
C15 C10 C9 119.2(6) . .
C10 C11 C12 120.8(7) . .
C10 C11 H11 119.6 . .
C12 C11 H11 119.6 . .
C13 C12 C11 118.3(6) . .
C13 C12 H12 120.8 . .
C11 C12 H12 120.8 . .
C12 C13 C14 122.4(6) . .
C12 C13 Br1 118.4(5) . .
C14 C13 Br1 119.2(5) . .
C13 C14 C15 118.1(7) . .
C13 C14 H14 121.0 . .
C15 C14 H14 121.0 . .
C14 C15 C10 120.8(7) . .
C14 C15 H15 119.6 . .
C10 C15 H15 119.6 . .
C1 N1 C8 110.4(5) . .
C1 N1 H1 124.8 . .
C8 N1 H1 124.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.232(8) .
C1 N1 1.368(9) .
C1 C2 1.498(9) .
C2 C9 1.361(9) .
C2 C3 1.447(10) .
C3 C8 1.408(9) .
C3 C4 1.409(10) .
C4 C5 1.389(10) .
C4 H4 0.9500 .
C5 C6 1.394(9) .
C5 H5 0.9500 .
C6 C7 1.393(10) .
C6 H6 0.9500 .
C7 C8 1.386(9) .
C7 H7 0.9500 .
C8 N1 1.397(9) .
C9 C10 1.482(9) .
C9 H9 0.9500 .
C10 C11 1.388(9) .
C10 C15 1.394(10) .
C11 C12 1.393(9) .
C11 H11 0.9500 .
C12 C13 1.388(10) .
C12 H12 0.9500 .
C13 C14 1.388(10) .
C13 Br1 1.906(6) .
C14 C15 1.394(9) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N1 H1 0.8800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88 1.98 2.843(7) 166.8 7_536
