#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:58:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180325 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/39/7153998.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_7153998
loop_
_publ_author_name
'Liu, Xiaozu'
'Hu, Qinghong'
'Yuan, Zeli'
'Liu, Peijun'
_publ_section_title
;
 AcOH-mediated dichloroimination of indoles using chloramine-B: a facile
 access to 2,3-functionalized indolines.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7494
_journal_page_last               7497
_journal_paper_doi               10.1039/c4ob01179a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C17 H13 Br Cl2 N2 O2 S'
_chemical_formula_weight         460.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.670(3)
_cell_angle_beta                 101.817(4)
_cell_angle_gamma                93.100(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9358(18)
_cell_length_b                   9.326(2)
_cell_length_c                   12.002(3)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.82
_cell_volume                     931.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4776
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    2.620
_exptl_absorpt_correction_T_max  0.7439
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.620
_refine_diff_density_min         -2.251
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0770
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1414P)²+2.4968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2260
_refine_ls_wR_factor_ref         0.2417
_reflns_number_gt                2472
_reflns_number_total             3254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01179a2.cif
_cod_data_source_block           dj816_0m
_cod_depositor_comments
;Adding full bibliography for 7153998.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153998
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br -0.49015(11) -0.29166(11) 0.94239(10) 0.0845(4) Uani 1 1 d .
C1 C -0.3267(8) -0.0867(8) 0.8623(7) 0.0542(17) Uani 1 1 d .
H1 H -0.4159 -0.0397 0.8578 0.065 Uiso 1 1 calc R
C2 C -0.3195(9) -0.2138(8) 0.8966(7) 0.0551(17) Uani 1 1 d .
C3 C -0.1899(10) -0.2908(9) 0.9002(7) 0.0609(19) Uani 1 1 d .
H3 H -0.1898 -0.3794 0.9212 0.073 Uiso 1 1 calc R
C4 C -0.0606(9) -0.2329(8) 0.8719(7) 0.0552(17) Uani 1 1 d .
H4 H 0.0276 -0.2816 0.8738 0.066 Uiso 1 1 calc R
C5 C -0.0669(8) -0.1026(8) 0.8413(6) 0.0530(8) Uani 1 1 d U
C6 C -0.1985(8) -0.0297(8) 0.8345(6) 0.0522(8) Uani 1 1 d U
C7 C -0.1709(8) 0.1022(8) 0.7936(6) 0.0522(8) Uani 1 1 d U
C8 C 0.0026(8) 0.1075(8) 0.7916(6) 0.0531(8) Uani 1 1 d U
C9 C 0.1976(9) 0.3563(8) 0.6539(7) 0.0543(17) Uani 1 1 d .
C10 C 0.3528(11) 0.3481(11) 0.6888(9) 0.076(2) Uani 1 1 d .
H10 H 0.3960 0.3452 0.7654 0.091 Uiso 1 1 calc R
C11 C 0.1362(11) 0.3626(11) 0.5412(8) 0.075(2) Uani 1 1 d .
H11 H 0.0311 0.3667 0.5172 0.089 Uiso 1 1 calc R
C12 C 0.2300(14) 0.3629(12) 0.4636(9) 0.089(3) Uani 1 1 d .
H12 H 0.1894 0.3724 0.3886 0.107 Uiso 1 1 calc R
C13 C 0.3806(15) 0.3494(11) 0.4964(11) 0.092(3) Uani 1 1 d .
H13 H 0.4423 0.3436 0.4419 0.111 Uiso 1 1 calc R
C14 C 0.4432(12) 0.3442(13) 0.6071(12) 0.093(3) Uani 1 1 d .
H14 H 0.5481 0.3379 0.6289 0.111 Uiso 1 1 calc R
C15 C 0.2171(9) -0.1320(9) 0.6958(7) 0.0674(10) Uani 1 1 d DU
H15 H 0.1642 -0.0812 0.6467 0.081 Uiso 1 1 calc R
C16 C 0.2783(10) -0.2491(9) 0.6237(8) 0.0787(13) Uani 1 1 d DU
H16A H 0.3356 -0.3128 0.6575 0.094 Uiso 1 1 calc R
H16B H 0.2618 -0.2633 0.5420 0.094 Uiso 1 1 calc R
C17 C 0.2040(9) -0.0612(9) 0.8120(7) 0.0606(8) Uani 1 1 d U
H17A H 0.2781 0.0286 0.8470 0.073 Uiso 1 1 calc R
H17B H 0.2273 -0.1285 0.8600 0.073 Uiso 1 1 calc R
Cl1 Cl -0.2123(2) 0.2711(2) 0.88689(19) 0.0625(6) Uani 1 1 d .
Cl2 Cl -0.2792(3) 0.0643(3) 0.64213(19) 0.0725(6) Uani 1 1 d .
N1 N 0.0496(7) -0.0200(7) 0.8134(5) 0.0550(8) Uani 1 1 d U
N2 N 0.0990(7) 0.1999(7) 0.7747(6) 0.0570(15) Uani 1 1 d .
O1 O 0.1485(8) 0.4756(6) 0.8633(6) 0.0769(17) Uani 1 1 d .
O2 O -0.0748(7) 0.3767(7) 0.6965(6) 0.0765(16) Uani 1 1 d .
S1 S 0.0775(2) 0.3639(2) 0.75443(19) 0.0586(5) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 '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 118.3(7)
C2 C1 H1 120.8
C6 C1 H1 120.8
C1 C2 C3 122.5(7)
C1 C2 Br1 119.8(6)
C3 C2 Br1 117.6(6)
C4 C3 C2 118.9(7)
C4 C3 H3 120.5
C2 C3 H3 120.5
C5 C4 C3 118.2(7)
C5 C4 H4 120.9
C3 C4 H4 120.9
C4 C5 C6 122.2(7)
C4 C5 N1 128.7(7)
C6 C5 N1 109.1(6)
C1 C6 C5 119.7(7)
C1 C6 C7 131.3(7)
C5 C6 C7 108.9(6)
C6 C7 C8 103.2(6)
C6 C7 Cl1 113.4(5)
C8 C7 Cl1 111.8(5)
C6 C7 Cl2 109.2(5)
C8 C7 Cl2 107.6(5)
Cl1 C7 Cl2 111.1(4)
N2 C8 N1 119.2(7)
N2 C8 C7 134.5(7)
N1 C8 C7 106.3(6)
C11 C9 C10 120.0(8)
C11 C9 S1 119.4(7)
C10 C9 S1 120.5(6)
C9 C10 C14 118.5(9)
C9 C10 H10 120.8
C14 C10 H10 120.8
C9 C11 C12 119.9(9)
C9 C11 H11 120.0
C12 C11 H11 120.0
C13 C12 C11 119.9(10)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 120.8(9)
C12 C13 H13 119.6
C14 C13 H13 119.6
C13 C14 C10 120.7(10)
C13 C14 H14 119.6
C10 C14 H14 119.6
C17 C15 C16 144.8(9)
C17 C15 H15 107.6
C16 C15 H15 107.6
C15 C16 H16A 120.0
C15 C16 H16B 120.0
H16A C16 H16B 120.0
C15 C17 N1 111.1(7)
C15 C17 H17A 109.4
N1 C17 H17A 109.4
C15 C17 H17B 109.4
N1 C17 H17B 109.4
H17A C17 H17B 108.0
C8 N1 C5 111.9(6)
C8 N1 C17 123.1(6)
C5 N1 C17 124.9(6)
C8 N2 S1 129.6(5)
O1 S1 O2 118.3(4)
O1 S1 N2 107.5(4)
O2 S1 N2 114.1(4)
O1 S1 C9 108.0(4)
O2 S1 C9 108.6(4)
N2 S1 C9 98.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.899(7)
C1 C2 1.362(10)
C1 C6 1.378(10)
C1 H1 0.9300
C2 C3 1.395(11)
C3 C4 1.393(12)
C3 H3 0.9300
C4 C5 1.367(10)
C4 H4 0.9300
C5 C6 1.390(10)
C5 N1 1.412(10)
C6 C7 1.476(10)
C7 C8 1.554(10)
C7 Cl1 1.759(7)
C7 Cl2 1.800(7)
C8 N2 1.272(9)
C8 N1 1.359(10)
C9 C11 1.371(12)
C9 C10 1.377(12)
C9 S1 1.761(7)
C10 C14 1.386(14)
C10 H10 0.9300
C11 C12 1.375(14)
C11 H11 0.9300
C12 C13 1.346(16)
C12 H12 0.9300
C13 C14 1.348(16)
C13 H13 0.9300
C14 H14 0.9300
C15 C17 1.394(11)
C15 C16 1.3986(11)
C15 H15 0.9300
C16 H16A 0.9300
C16 H16B 0.9300
C17 N1 1.454(10)
C17 H17A 0.9700
C17 H17B 0.9700
N2 S1 1.631(6)
O1 S1 1.416(6)
O2 S1 1.423(6)
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 -2.5(12)
C6 C1 C2 Br1 177.3(5)
C1 C2 C3 C4 2.4(12)
Br1 C2 C3 C4 -177.4(6)
C2 C3 C4 C5 -0.2(11)
C3 C4 C5 C6 -1.8(11)
C3 C4 C5 N1 177.5(7)
C2 C1 C6 C5 0.4(11)
C2 C1 C6 C7 179.0(7)
C4 C5 C6 C1 1.8(11)
N1 C5 C6 C1 -177.7(6)
C4 C5 C6 C7 -177.2(7)
N1 C5 C6 C7 3.4(8)
C1 C6 C7 C8 174.8(8)
C5 C6 C7 C8 -6.5(8)
C1 C6 C7 Cl1 53.6(10)
C5 C6 C7 Cl1 -127.6(6)
C1 C6 C7 Cl2 -70.9(9)
C5 C6 C7 Cl2 107.8(6)
C6 C7 C8 N2 -172.8(8)
Cl1 C7 C8 N2 -50.5(11)
Cl2 C7 C8 N2 71.8(10)
C6 C7 C8 N1 7.3(7)
Cl1 C7 C8 N1 129.6(5)
Cl2 C7 C8 N1 -108.1(6)
C11 C9 C10 C14 -0.9(13)
S1 C9 C10 C14 -179.2(8)
C10 C9 C11 C12 -1.0(13)
S1 C9 C11 C12 177.4(7)
C9 C11 C12 C13 3.3(15)
C11 C12 C13 C14 -3.8(16)
C12 C13 C14 C10 1.9(17)
C9 C10 C14 C13 0.5(16)
C16 C15 C17 N1 -139.4(13)
N2 C8 N1 C5 174.4(7)
C7 C8 N1 C5 -5.8(8)
N2 C8 N1 C17 -3.6(11)
C7 C8 N1 C17 176.3(6)
C4 C5 N1 C8 -177.7(8)
C6 C5 N1 C8 1.7(8)
C4 C5 N1 C17 0.2(12)
C6 C5 N1 C17 179.6(6)
C15 C17 N1 C8 -82.5(9)
C15 C17 N1 C5 99.9(9)
N1 C8 N2 S1 -176.2(6)
C7 C8 N2 S1 4.0(14)
C8 N2 S1 O1 102.7(8)
C8 N2 S1 O2 -30.6(9)
C8 N2 S1 C9 -145.4(7)
C11 C9 S1 O1 -129.7(7)
C10 C9 S1 O1 48.7(7)
C11 C9 S1 O2 -0.2(8)
C10 C9 S1 O2 178.1(7)
C11 C9 S1 N2 118.7(7)
C10 C9 S1 N2 -62.9(7)
