#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/81/1518126.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_1518126
loop_
_publ_author_name
'Inami, Tasuku'
'Kurahashi, Takuya'
'Matsubara, Seijiro'
_publ_section_title
;
 Nickel-catalyzed reaction of thioisatins and alkynes: a facile synthesis
 of thiochromones.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5660
_journal_page_last               5662
_journal_paper_doi               10.1021/ol5026102
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C21 H12 Br2 O S'
_chemical_formula_weight         472.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4731(8)
_cell_length_b                   14.7286(11)
_cell_length_c                   11.7998(9)
_cell_measurement_reflns_used    4021
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.21
_cell_volume                     1817.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10891
_diffrn_reflns_theta_full        27.01
_diffrn_reflns_theta_max         27.01
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    4.582
_exptl_absorpt_correction_T_max  0.7398
_exptl_absorpt_correction_T_min  0.6572
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0315
_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)+(0.0472P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                3089
_reflns_number_total             3944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5026102_si_005.cif
_cod_data_source_block           3aq
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--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 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 1518126--1518130.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1518126
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.64655(2) 0.21716(2) 0.69976(3) 0.05734(11) Uani 1 1 d .
Br2 Br 0.34267(3) 0.045347(18) 0.35125(2) 0.05708(11) Uani 1 1 d .
O1 O 0.06658(19) 0.15992(13) 0.69130(18) 0.0622(5) Uani 1 1 d .
C1 C 0.3597(2) 0.13088(15) 0.4716(2) 0.0402(5) Uani 1 1 d .
C2 C 0.2659(2) 0.24151(15) 0.5880(2) 0.0372(5) Uani 1 1 d .
C3 C 0.4884(2) 0.20394(16) 0.6141(2) 0.0424(6) Uani 1 1 d .
C4 C 0.1549(2) 0.29460(15) 0.6263(2) 0.0373(5) Uani 1 1 d .
C5 C 0.1437(2) 0.38541(16) 0.6050(2) 0.0384(5) Uani 1 1 d .
C6 C -0.0138(2) 0.29262(16) 0.7714(2) 0.0408(5) Uani 1 1 d .
C7 C 0.0669(2) 0.24297(17) 0.6933(2) 0.0429(6) Uani 1 1 d .
C8 C -0.0306(2) 0.38592(17) 0.7683(2) 0.0435(6) Uani 1 1 d .
C9 C 0.4782(2) 0.14367(16) 0.5252(2) 0.0432(6) Uani 1 1 d .
H9 H 0.5494 0.1125 0.5021 0.052 Uiso 1 1 calc R
C10 C 0.3843(2) 0.25408(16) 0.6453(2) 0.0402(5) Uani 1 1 d .
H10 H 0.3935 0.2959 0.7043 0.048 Uiso 1 1 calc R
C11 C 0.2247(2) 0.43699(16) 0.5282(2) 0.0393(5) Uani 1 1 d .
C12 C 0.2527(2) 0.17751(16) 0.5021(2) 0.0415(5) Uani 1 1 d .
H12 H 0.1732 0.1662 0.4657 0.050 Uiso 1 1 calc R
C13 C 0.2469(3) 0.40319(18) 0.4210(2) 0.0501(6) Uani 1 1 d .
H13 H 0.2126 0.3475 0.3981 0.060 Uiso 1 1 calc R
C14 C 0.2746(3) 0.52094(18) 0.5594(2) 0.0503(6) Uani 1 1 d .
H14 H 0.2583 0.5453 0.6298 0.060 Uiso 1 1 calc R
C15 C -0.0980(3) 0.4309(2) 0.8513(3) 0.0574(7) Uani 1 1 d .
H15 H -0.1086 0.4936 0.8490 0.069 Uiso 1 1 calc R
C16 C -0.1480(3) 0.3800(2) 0.9361(3) 0.0658(8) Uani 1 1 d .
H16 H -0.1916 0.4090 0.9922 0.079 Uiso 1 1 calc R
C17 C -0.0687(2) 0.24291(19) 0.8583(2) 0.0487(6) Uani 1 1 d .
H17 H -0.0602 0.1801 0.8607 0.058 Uiso 1 1 calc R
C18 C -0.1346(3) 0.2868(2) 0.9394(3) 0.0600(8) Uani 1 1 d .
H18 H -0.1704 0.2536 0.9966 0.072 Uiso 1 1 calc R
S3 S 0.03065(6) 0.45470(4) 0.66337(6) 0.04971(18) Uani 1 1 d .
C19 C 0.3198(3) 0.4521(2) 0.3485(3) 0.0649(8) Uani 1 1 d .
H19 H 0.3343 0.4292 0.2769 0.078 Uiso 1 1 calc R
C20 C 0.3709(3) 0.5344(2) 0.3817(3) 0.0689(9) Uani 1 1 d .
H20 H 0.4209 0.5667 0.3330 0.083 Uiso 1 1 calc R
C21 C 0.3486(3) 0.5691(2) 0.4865(3) 0.0645(8) Uani 1 1 d .
H21 H 0.3830 0.6249 0.5087 0.077 Uiso 1 1 calc R
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'
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'
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
C9 C1 C12 122.5(2)
C9 C1 Br2 118.59(17)
C12 C1 Br2 118.91(18)
C12 C2 C10 119.7(2)
C12 C2 C4 122.1(2)
C10 C2 C4 118.1(2)
C9 C3 C10 121.3(2)
C9 C3 Br1 119.97(18)
C10 C3 Br1 118.67(19)
C5 C4 C7 124.0(2)
C5 C4 C2 121.2(2)
C7 C4 C2 114.7(2)
C4 C5 C11 124.6(2)
C4 C5 S3 123.81(19)
C11 C5 S3 111.62(17)
C8 C6 C17 118.6(2)
C8 C6 C7 123.3(2)
C17 C6 C7 117.9(2)
O1 C7 C4 120.7(2)
O1 C7 C6 120.4(2)
C4 C7 C6 118.7(2)
C6 C8 C15 121.1(2)
C6 C8 S3 122.8(2)
C15 C8 S3 116.1(2)
C1 C9 C3 118.0(2)
C1 C9 H9 121.0
C3 C9 H9 121.0
C3 C10 C2 119.6(2)
C3 C10 H10 120.2
C2 C10 H10 120.2
C14 C11 C13 118.7(2)
C14 C11 C5 121.0(2)
C13 C11 C5 120.2(2)
C1 C12 C2 118.8(2)
C1 C12 H12 120.6
C2 C12 H12 120.6
C19 C13 C11 120.3(3)
C19 C13 H13 119.9
C11 C13 H13 119.9
C11 C14 C21 120.5(3)
C11 C14 H14 119.7
C21 C14 H14 119.7
C16 C15 C8 118.5(3)
C16 C15 H15 120.8
C8 C15 H15 120.8
C15 C16 C18 121.3(3)
C15 C16 H16 119.4
C18 C16 H16 119.4
C18 C17 C6 120.3(3)
C18 C17 H17 119.8
C6 C17 H17 119.8
C17 C18 C16 120.2(3)
C17 C18 H18 119.9
C16 C18 H18 119.9
C5 S3 C8 103.11(12)
C20 C19 C13 120.2(3)
C20 C19 H19 119.9
C13 C19 H19 119.9
C21 C20 C19 120.2(3)
C21 C20 H20 119.9
C19 C20 H20 119.9
C20 C21 C14 120.0(3)
C20 C21 H21 120.0
C14 C21 H21 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.899(2)
Br2 C1 1.899(2)
O1 C7 1.223(3)
C1 C9 1.374(3)
C1 C12 1.380(3)
C2 C12 1.385(3)
C2 C10 1.390(3)
C2 C4 1.493(3)
C3 C9 1.374(3)
C3 C10 1.385(3)
C4 C5 1.365(3)
C4 C7 1.462(3)
C5 C11 1.486(3)
C5 S3 1.735(2)
C6 C8 1.386(3)
C6 C17 1.409(4)
C6 C7 1.479(3)
C8 C15 1.406(4)
C8 S3 1.750(3)
C9 H9 0.9300
C10 H10 0.9300
C11 C14 1.384(4)
C11 C13 1.391(4)
C12 H12 0.9300
C13 C19 1.381(4)
C13 H13 0.9300
C14 C21 1.385(4)
C14 H14 0.9300
C15 C16 1.378(4)
C15 H15 0.9300
C16 C18 1.380(4)
C16 H16 0.9300
C17 C18 1.373(4)
C17 H17 0.9300
C18 H18 0.9300
C19 C20 1.373(5)
C19 H19 0.9300
C20 C21 1.370(5)
C20 H20 0.9300
C21 H21 0.9300
