#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:07:06 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179913 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/08/7020845.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_7020845
loop_
_publ_author_name
'Singh, Atul P.'
'Murale, Dhiraj P.'
'Ha, Yonghwang'
'Liew, Hyunjeong'
'Lee, Kang Mun'
'Segev, Aviv'
'Suh, Yoo-Hun'
'Churchill, David G.'
_publ_section_title
;
 A novel, selective, and extremely responsive thienyl-based dual
 fluorogenic probe for tandem superoxide and Hg2+ chemosensing
;
_journal_issue                   10
_journal_name_full               'Dalton Transactions'
_journal_page_first              3285
_journal_paper_doi               10.1039/c2dt32135a
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         C22H19B1Br1F2N3S2
_chemical_formula_sum            'C22 H19 B Br F2 N3 S2'
_chemical_formula_weight         518.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.942(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5410(14)
_cell_length_b                   11.291(2)
_cell_length_c                   27.486(5)
_cell_measurement_reflns_used    6972
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.38
_cell_measurement_theta_min      1.49
_cell_volume                     2327.7(7)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  'Bruker SHELXTL'
_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_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  0.1663
_diffrn_reflns_av_sigmaI/netI    0.2005
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            38634
_diffrn_reflns_theta_full        30.38
_diffrn_reflns_theta_max         30.38
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cubic
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2729
_refine_ls_R_factor_gt           0.0671
_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)+(0.0542P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1691
_reflns_number_gt                2152
_reflns_number_total             6972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt32135a.txt
_cod_data_source_block           nchu90-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7020845
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
B B 0.4401(8) 0.5227(5) 0.2089(2) 0.0549(15) Uani 1 1 d .
F1 F 0.5496(4) 0.6102(2) 0.19334(13) 0.0899(10) Uani 1 1 d .
F2 F 0.4287(4) 0.5378(3) 0.25838(11) 0.0888(10) Uani 1 1 d .
N1 N 0.5148(5) 0.3995(3) 0.19886(14) 0.0535(10) Uani 1 1 d .
N2 N 0.2522(5) 0.5318(3) 0.18067(13) 0.0523(10) Uani 1 1 d .
N3 N 0.4554(7) 0.1812(5) 0.00240(19) 0.0913(14) Uani 1 1 d .
S1 S 0.0491(2) 0.12192(13) 0.03676(5) 0.0774(5) Uani 1 1 d .
S2 S 0.2360(2) 0.35773(13) 0.02649(5) 0.0856(5) Uani 1 1 d .
Br Br -0.10046(8) -0.07694(5) 0.09940(2) 0.0877(3) Uani 1 1 d .
C1 C 0.6744(7) 0.3546(5) 0.21840(18) 0.0636(14) Uani 1 1 d .
C2 C 0.6909(7) 0.2406(5) 0.2000(2) 0.0702(15) Uani 1 1 d .
H2 H 0.7875 0.1905 0.2078 0.084 Uiso 1 1 calc R
C3 C 0.5430(7) 0.2135(4) 0.16855(18) 0.0655(14) Uani 1 1 d .
C4 C 0.4289(6) 0.3145(4) 0.16801(16) 0.0491(12) Uani 1 1 d .
C5 C 0.2581(6) 0.3361(4) 0.14494(15) 0.0469(11) Uani 1 1 d .
C6 C 0.1672(6) 0.4427(4) 0.15139(16) 0.0489(11) Uani 1 1 d .
C7 C -0.0054(6) 0.4839(5) 0.13371(17) 0.0581(13) Uani 1 1 d .
C8 C -0.0190(7) 0.5958(4) 0.1525(2) 0.0673(15) Uani 1 1 d .
H8 H -0.1180 0.6450 0.1471 0.081 Uiso 1 1 calc R
C9 C 0.1388(7) 0.6240(4) 0.18111(19) 0.0620(14) Uani 1 1 d .
C10 C 0.1639(6) 0.2433(4) 0.06308(18) 0.0602(13) Uani 1 1 d .
C11 C 0.1691(6) 0.2421(4) 0.11317(17) 0.0512(12) Uani 1 1 d .
C12 C 0.0819(6) 0.1415(4) 0.13068(18) 0.0563(13) Uani 1 1 d .
H12 H 0.0722 0.1263 0.1636 0.068 Uiso 1 1 calc R
C13 C 0.0148(6) 0.0708(4) 0.09351(18) 0.0620(13) Uani 1 1 d .
C14 C 0.4027(7) 0.2922(5) -0.00613(18) 0.0676(15) Uani 1 1 d .
C15 C 0.4758(11) 0.3612(6) -0.0393(3) 0.123(3) Uani 1 1 d .
H15 H 0.4391 0.4396 -0.0434 0.148 Uiso 1 1 calc R
C16 C 0.6025(12) 0.3178(8) -0.0667(3) 0.151(4) Uani 1 1 d .
H16 H 0.6526 0.3659 -0.0892 0.181 Uiso 1 1 calc R
C17 C 0.6519(11) 0.2061(8) -0.0607(3) 0.132(3) Uani 1 1 d .
H17 H 0.7341 0.1731 -0.0798 0.158 Uiso 1 1 calc R
C18 C 0.5816(9) 0.1409(7) -0.0266(3) 0.120(3) Uani 1 1 d .
H18 H 0.6208 0.0632 -0.0222 0.144 Uiso 1 1 calc R
C19 C 0.5131(8) 0.0978(5) 0.1410(2) 0.0911(19) Uani 1 1 d .
H19A H 0.6200 0.0511 0.1453 0.137 Uiso 1 1 calc R
H19B H 0.4830 0.1139 0.1069 0.137 Uiso 1 1 calc R
H19C H 0.4175 0.0551 0.1535 0.137 Uiso 1 1 calc R
C20 C 0.8001(7) 0.4181(5) 0.2540(2) 0.0843(17) Uani 1 1 d .
H20A H 0.8357 0.4908 0.2398 0.126 Uiso 1 1 calc R
H20B H 0.9033 0.3696 0.2625 0.126 Uiso 1 1 calc R
H20C H 0.7432 0.4350 0.2829 0.126 Uiso 1 1 calc R
C21 C -0.1492(7) 0.4206(5) 0.1022(2) 0.0812(17) Uani 1 1 d .
H21A H -0.2623 0.4566 0.1059 0.122 Uiso 1 1 calc R
H21B H -0.1519 0.3389 0.1118 0.122 Uiso 1 1 calc R
H21C H -0.1257 0.4256 0.0686 0.122 Uiso 1 1 calc R
C22 C 0.1827(8) 0.7361(4) 0.2084(2) 0.0905(18) Uani 1 1 d .
H22A H 0.1688 0.7245 0.2424 0.136 Uiso 1 1 calc R
H22B H 0.1038 0.7978 0.1955 0.136 Uiso 1 1 calc R
H22C H 0.3037 0.7581 0.2049 0.136 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
F1 B F2 108.4(4)
F1 B N1 110.5(4)
F2 B N1 110.4(4)
F1 B N2 110.1(4)
F2 B N2 109.7(4)
N1 B N2 107.8(4)
C1 N1 C4 108.6(4)
C1 N1 B 126.3(4)
C4 N1 B 125.1(4)
C9 N2 C6 107.9(4)
C9 N2 B 126.6(4)
C6 N2 B 125.5(4)
C14 N3 C18 114.9(5)
C13 S1 C10 90.1(2)
C10 S2 C14 105.0(2)
N1 C1 C2 108.0(5)
N1 C1 C20 124.1(5)
C2 C1 C20 127.9(5)
C3 C2 C1 109.7(5)
C2 C3 C4 106.1(4)
C2 C3 C19 125.1(5)
C4 C3 C19 128.7(5)
N1 C4 C5 120.3(4)
N1 C4 C3 107.6(4)
C5 C4 C3 132.1(5)
C4 C5 C6 122.1(4)
C4 C5 C11 118.7(4)
C6 C5 C11 119.2(4)
N2 C6 C5 119.1(4)
N2 C6 C7 108.1(4)
C5 C6 C7 132.8(5)
C8 C7 C6 105.9(4)
C8 C7 C21 125.4(5)
C6 C7 C21 128.7(5)
C7 C8 C9 109.3(4)
N2 C9 C8 108.9(4)
N2 C9 C22 123.5(5)
C8 C9 C22 127.6(5)
C11 C10 S1 111.7(3)
C11 C10 S2 127.1(4)
S1 C10 S2 120.8(3)
C10 C11 C12 112.4(4)
C10 C11 C5 123.0(4)
C12 C11 C5 124.6(4)
C13 C12 C11 111.5(4)
C12 C13 S1 114.2(4)
C12 C13 Br 126.4(4)
S1 C13 Br 119.3(3)
N3 C14 C15 121.6(5)
N3 C14 S2 121.2(4)
C15 C14 S2 117.2(5)
C14 C15 C16 121.3(6)
C17 C16 C15 118.5(7)
C16 C17 C18 119.0(7)
C17 C18 N3 124.6(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B F1 1.383(6)
B F2 1.383(6)
B N1 1.536(6)
B N2 1.546(6)
N1 C1 1.363(6)
N1 C4 1.395(5)
N2 C9 1.348(5)
N2 C6 1.401(5)
N3 C14 1.329(6)
N3 C18 1.380(8)
S1 C13 1.708(5)
S1 C10 1.738(5)
S2 C10 1.757(5)
S2 C14 1.779(5)
Br C13 1.896(5)
C1 C2 1.394(7)
C1 C20 1.476(7)
C2 C3 1.372(6)
C3 C4 1.428(6)
C3 C19 1.515(7)
C4 C5 1.397(6)
C5 C6 1.406(6)
C5 C11 1.489(6)
C6 C7 1.419(6)
C7 C8 1.373(6)
C7 C21 1.499(7)
C8 C9 1.393(7)
C9 C22 1.491(6)
C10 C11 1.374(6)
C11 C12 1.421(6)
C12 C13 1.353(6)
C14 C15 1.358(7)
C15 C16 1.368(9)
C16 C17 1.321(9)
C17 C18 1.344(9)
