#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/61/1516132.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_1516132
loop_
_publ_author_name
'Ravi, Chitrakar'
'Chandra Mohan, Darapaneni'
'Adimurthy, Subbarayappa'
_publ_section_title
;
 N-chlorosuccinimide-promoted regioselective sulfenylation of
 imidazoheterocycles at room temperature.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2978
_journal_page_last               2981
_journal_paper_doi               10.1021/ol501117z
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C19 H14 Br N2 O0.5 S'
_chemical_formula_weight         390.29
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.457(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.406(2)
_cell_length_b                   14.522(3)
_cell_length_c                   20.970(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3363.4(11)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9618
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    2.572
_exptl_absorpt_correction_T_max  0.6989
_exptl_absorpt_correction_T_min  0.4260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCKS
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.530
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0532P)²+2.1282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2936
_reflns_number_total             3674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501117z_si_002.cif
_cod_data_source_block           adi13m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516132.cif.
;
_cod_original_cell_volume        3363.4(12)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C19 H14 Br N2 O0.50 S'
_cod_database_code               1516132
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
O1 O 0.0000 0.41127(18) 0.7500 0.0665(8) Uani 1 2 d S
Br1 Br -0.01680(3) 0.24014(2) 0.428193(15) 0.07146(14) Uani 1 1 d .
S1 S 0.35636(5) 0.62876(4) 0.58909(3) 0.04828(16) Uani 1 1 d .
N1 N 0.26844(15) 0.65031(12) 0.69836(9) 0.0398(4) Uani 1 1 d .
N2 N 0.12380(16) 0.54350(13) 0.68945(9) 0.0438(4) Uani 1 1 d .
C1 C 0.17942(18) 0.61401(15) 0.72548(11) 0.0414(5) Uani 1 1 d .
C2 C 0.1611(2) 0.65282(18) 0.78337(12) 0.0527(6) Uani 1 1 d .
H2 H 0.1025 0.6291 0.8027 0.063 Uiso 1 1 calc R
C3 C 0.2303(3) 0.7255(2) 0.81082(14) 0.0596(7) Uani 1 1 d .
H3 H 0.2191 0.7516 0.8494 0.072 Uiso 1 1 calc R
C4 C 0.3185(3) 0.76176(18) 0.78161(15) 0.0594(7) Uani 1 1 d .
H4 H 0.3642 0.8122 0.8008 0.071 Uiso 1 1 calc R
C5 C 0.3378(2) 0.72462(16) 0.72637(13) 0.0487(5) Uani 1 1 d .
H5 H 0.3968 0.7486 0.7074 0.058 Uiso 1 1 calc R
C6 C 0.26763(19) 0.59923(15) 0.64242(11) 0.0411(5) Uani 1 1 d .
C7 C 0.17750(18) 0.53373(15) 0.63842(11) 0.0401(5) Uani 1 1 d .
C8 C 0.13443(19) 0.46233(15) 0.58881(11) 0.0411(5) Uani 1 1 d .
C9 C 0.2078(2) 0.42363(16) 0.55209(12) 0.0495(5) Uani 1 1 d .
H9 H 0.2882 0.4422 0.5596 0.059 Uiso 1 1 calc R
C10 C 0.1631(2) 0.35791(17) 0.50461(13) 0.0544(6) Uani 1 1 d .
H10 H 0.2128 0.3329 0.4800 0.065 Uiso 1 1 calc R
C11 C 0.0449(2) 0.32982(16) 0.49394(12) 0.0517(6) Uani 1 1 d .
C12 C -0.0298(2) 0.36532(17) 0.53042(12) 0.0537(6) Uani 1 1 d .
H12 H -0.1093 0.3449 0.5235 0.064 Uiso 1 1 calc R
C13 C 0.0150(2) 0.43134(18) 0.57729(12) 0.0484(5) Uani 1 1 d .
H13 H -0.0353 0.4558 0.6018 0.058 Uiso 1 1 calc R
C14 C 0.48578(18) 0.55597(16) 0.61367(11) 0.0417(5) Uani 1 1 d .
C15 C 0.5688(2) 0.5577(2) 0.57538(14) 0.0616(7) Uani 1 1 d .
H15 H 0.5567 0.5964 0.5390 0.074 Uiso 1 1 calc R
C16 C 0.6702(3) 0.5013(2) 0.59174(16) 0.0692(8) Uani 1 1 d .
H16 H 0.7247 0.5015 0.5654 0.083 Uiso 1 1 calc R
C17 C 0.6910(2) 0.4459(2) 0.64557(14) 0.0584(6) Uani 1 1 d .
H17 H 0.7607 0.4101 0.6569 0.070 Uiso 1 1 calc R
C18 C 0.6083(2) 0.4434(2) 0.68289(13) 0.0653(7) Uani 1 1 d .
H18 H 0.6211 0.4047 0.7193 0.078 Uiso 1 1 calc R
C19 C 0.5057(2) 0.4981(2) 0.66679(12) 0.0597(7) Uani 1 1 d .
H19 H 0.4498 0.4954 0.6923 0.072 Uiso 1 1 calc R
H1C H 0.043(3) 0.442(3) 0.7296(17) 0.094(12) Uiso 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'
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'
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
C6 S1 C14 103.91(10)
C5 N1 C1 121.6(2)
C5 N1 C6 131.35(19)
C1 N1 C6 107.04(18)
C1 N2 C7 106.28(17)
N2 C1 N1 110.66(19)
N2 C1 C2 130.3(2)
N1 C1 C2 119.1(2)
C3 C2 C1 119.0(2)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 120.7(3)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 121.0(2)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 N1 118.7(2)
C4 C5 H5 120.7
N1 C5 H5 120.7
N1 C6 C7 105.45(18)
N1 C6 S1 122.03(16)
C7 C6 S1 132.18(18)
N2 C7 C6 110.58(19)
N2 C7 C8 119.57(18)
C6 C7 C8 129.8(2)
C9 C8 C13 118.0(2)
C9 C8 C7 122.6(2)
C13 C8 C7 119.4(2)
C10 C9 C8 120.9(2)
C10 C9 H9 119.6
C8 C9 H9 119.6
C11 C10 C9 119.6(2)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 121.1(2)
C10 C11 Br1 119.5(2)
C12 C11 Br1 119.40(19)
C13 C12 C11 119.1(2)
C13 C12 H12 120.5
C11 C12 H12 120.5
C12 C13 C8 121.3(2)
C12 C13 H13 119.4
C8 C13 H13 119.4
C19 C14 C15 119.0(2)
C19 C14 S1 123.81(17)
C15 C14 S1 117.22(18)
C14 C15 C16 119.6(3)
C14 C15 H15 120.2
C16 C15 H15 120.2
C17 C16 C15 121.2(2)
C17 C16 H16 119.4
C15 C16 H16 119.4
C16 C17 C18 119.2(2)
C16 C17 H17 120.4
C18 C17 H17 120.4
C17 C18 C19 120.5(3)
C17 C18 H18 119.8
C19 C18 H18 119.8
C14 C19 C18 120.6(2)
C14 C19 H19 119.7
C18 C19 H19 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1C 0.86(3)
Br1 C11 1.899(2)
S1 C6 1.739(2)
S1 C14 1.784(2)
N1 C5 1.380(3)
N1 C1 1.386(3)
N1 C6 1.386(3)
N2 C1 1.335(3)
N2 C7 1.367(3)
C1 C2 1.400(3)
C2 C3 1.357(4)
C2 H2 0.9300
C3 C4 1.404(4)
C3 H3 0.9300
C4 C5 1.345(4)
C4 H4 0.9300
C5 H5 0.9300
C6 C7 1.388(3)
C7 C8 1.464(3)
C8 C9 1.390(3)
C8 C13 1.398(3)
C9 C10 1.382(4)
C9 H9 0.9300
C10 C11 1.373(4)
C10 H10 0.9300
C11 C12 1.379(4)
C12 C13 1.377(3)
C12 H12 0.9300
C13 H13 0.9300
C14 C19 1.369(3)
C14 C15 1.387(3)
C15 C16 1.388(4)
C15 H15 0.9300
C16 C17 1.358(4)
C16 H16 0.9300
C17 C18 1.368(4)
C17 H17 0.9300
C18 C19 1.385(4)
C18 H18 0.9300
C19 H19 0.9300
