#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/60/1516092.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_1516092
loop_
_publ_author_name
'Benniston, Andrew C.'
'Winstanley, Thomas P. L.'
'Lemmetyinen, Helge'
'Tkachenko, Nikolai V.'
'Harrington, Ross W.'
'Wills, Corinne'
_publ_section_title
;
 Large Stokes shift fluorescent dyes based on a highly substituted
 terephthalic acid core.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1374
_journal_page_last               1377
_journal_paper_doi               10.1021/ol300038e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C12 H12 Br2 O6'
_chemical_formula_sum            'C12 H12 Br2 O6'
_chemical_formula_weight         412.04
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.576(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6055(4)
_cell_length_b                   7.7143(3)
_cell_length_c                   18.8681(8)
_cell_measurement_reflns_used    2406
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.7547
_cell_measurement_theta_min      2.8477
_cell_volume                     1395.40(10)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'thick-slice ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5024
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.81
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    5.831
_exptl_absorpt_correction_T_max  0.5932
_exptl_absorpt_correction_T_min  0.1789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Thu Jan 20 10:02:00 2011'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.134
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       0.0020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0448
_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)+(0.0544P)²+0.6337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2103
_reflns_number_total             2672
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1a.CIF
_cod_data_source_block           acb114_1a
_cod_database_code               1516092
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
Br1 Br 1.31680(5) -0.14563(6) -0.01275(3) 0.0281(2) Uani 1 1 d .
Br2 Br 1.30916(5) -0.64736(6) -0.03109(3) 0.0250(2) Uani 1 1 d .
O1 O 1.1579(4) -0.0802(5) 0.1230(2) 0.0252(8) Uani 1 1 d .
H1 H 1.192(5) -0.166(7) 0.120(3) 0.025(17) Uiso 1 1 d .
O2 O 1.1080(4) -0.2034(4) -0.1574(2) 0.0317(9) Uani 1 1 d .
O3 O 1.1412(4) 0.0821(4) -0.17277(18) 0.0280(8) Uani 1 1 d .
O4 O 0.9466(4) -0.4084(4) 0.13734(18) 0.0224(8) Uani 1 1 d .
H4 H 0.907(5) -0.320(6) 0.139(3) 0.020(15) Uiso 1 1 d .
O5 O 1.2698(4) -0.4079(4) 0.14134(19) 0.0296(9) Uani 1 1 d .
O6 O 1.2197(3) -0.6912(4) 0.13960(18) 0.0214(7) Uani 1 1 d .
C1 C 1.0840(5) -0.0451(6) 0.0618(3) 0.0197(11) Uani 1 1 d .
C2 C 1.1318(5) -0.0657(6) -0.0058(3) 0.0188(10) Uani 1 1 d .
C3 C 1.0513(5) -0.0225(5) -0.0658(3) 0.0190(10) Uani 1 1 d .
C4 C 1.1048(5) -0.0397(6) -0.1381(3) 0.0199(10) Uani 1 1 d .
C5 C 1.1593(6) -0.2462(7) -0.2258(3) 0.0374(14) Uani 1 1 d .
H5A H 1.2190 -0.3507 -0.2214 0.045 Uiso 1 1 calc R
H5B H 1.2164 -0.1493 -0.2426 0.045 Uiso 1 1 calc R
C6 C 1.0409(6) -0.2783(10) -0.2773(3) 0.0532(18) Uani 1 1 d .
H6A H 1.0757 -0.3126 -0.3229 0.080 Uiso 1 1 calc R
H6B H 0.9851 -0.1724 -0.2835 0.080 Uiso 1 1 calc R
H6C H 0.9828 -0.3714 -0.2597 0.080 Uiso 1 1 calc R
C7 C 0.9697(5) -0.4488(6) 0.0691(3) 0.0180(10) Uani 1 1 d .
C8 C 1.1292(5) -0.5659(6) -0.0126(3) 0.0181(10) Uani 1 1 d .
C9 C 1.1005(5) -0.5171(6) 0.0556(2) 0.0175(10) Uani 1 1 d .
C10 C 1.2062(5) -0.5302(6) 0.1159(3) 0.0205(10) Uani 1 1 d .
C11 C 1.3227(5) -0.7239(7) 0.1971(3) 0.0269(11) Uani 1 1 d .
H11A H 1.2945 -0.8255 0.2248 0.032 Uiso 1 1 calc R
H11B H 1.3295 -0.6224 0.2292 0.032 Uiso 1 1 calc R
C12 C 1.4621(5) -0.7577(8) 0.1676(3) 0.0426(15) Uani 1 1 d .
H12A H 1.5303 -0.7875 0.2065 0.064 Uiso 1 1 calc R
H12B H 1.4932 -0.6536 0.1434 0.064 Uiso 1 1 calc R
H12C H 1.4538 -0.8542 0.1338 0.064 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'
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
C1 O1 H1 108(5) . .
C4 O2 C5 118.7(4) . .
C7 O4 H4 110(4) . .
C10 O6 C11 117.7(4) . .
O1 C1 C2 125.3(4) . .
O1 C1 C3 117.9(4) . 3_755
C2 C1 C3 116.8(5) . 3_755
C3 C2 C1 121.8(4) . .
C3 C2 Br1 120.3(3) . .
C1 C2 Br1 117.8(4) . .
C2 C3 C1 121.4(4) . 3_755
C2 C3 C4 121.6(4) . .
C1 C3 C4 117.0(5) 3_755 .
O3 C4 O2 125.8(4) . .
O3 C4 C3 123.6(4) . .
O2 C4 C3 110.7(4) . .
O2 C5 C6 109.5(4) . .
O2 C5 H5A 109.8 . .
C6 C5 H5A 109.8 . .
O2 C5 H5B 109.8 . .
C6 C5 H5B 109.8 . .
H5A C5 H5B 108.2 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O4 C7 C8 124.4(4) . 3_745
O4 C7 C9 117.4(4) . .
C8 C7 C9 118.1(4) 3_745 .
C9 C8 C7 121.7(4) . 3_745
C9 C8 Br2 119.9(4) . .
C7 C8 Br2 118.4(3) 3_745 .
C8 C9 C7 120.2(4) . .
C8 C9 C10 122.0(4) . .
C7 C9 C10 117.8(4) . .
O5 C10 O6 124.2(4) . .
O5 C10 C9 124.0(4) . .
O6 C10 C9 111.8(4) . .
O6 C11 C12 109.8(4) . .
O6 C11 H11A 109.7 . .
C12 C11 H11A 109.7 . .
O6 C11 H11B 109.7 . .
C12 C11 H11B 109.7 . .
H11A C11 H11B 108.2 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.893(4) .
Br2 C8 1.892(4) .
O1 C1 1.346(6) .
O1 H1 0.74(5) .
O2 C4 1.316(6) .
O2 C5 1.449(6) .
O3 C4 1.208(5) .
O4 C7 1.357(6) .
O4 H4 0.79(5) .
O5 C10 1.207(5) .
O6 C10 1.324(5) .
O6 C11 1.444(6) .
C1 C2 1.391(6) .
C1 C3 1.407(6) 3_755
C2 C3 1.371(7) .
C3 C1 1.407(6) 3_755
C3 C4 1.494(6) .
C5 C6 1.470(8) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.387(7) 3_745
C7 C9 1.400(6) .
C8 C9 1.385(6) .
C8 C7 1.387(7) 3_745
C9 C10 1.480(7) .
C11 C12 1.504(7) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
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
O1 H1 O5 0.74(5) 2.04(5) 2.760(5) 163(6) .
O4 H4 O3 0.79(5) 2.01(5) 2.751(5) 158(5) 3_755
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -178.2(4) . .
C3 C1 C2 C3 0.0(7) 3_755 .
O1 C1 C2 Br1 -1.2(6) . .
C3 C1 C2 Br1 177.0(3) 3_755 .
C1 C2 C3 C1 0.0(8) . 3_755
Br1 C2 C3 C1 -176.9(3) . 3_755
C1 C2 C3 C4 178.1(4) . .
Br1 C2 C3 C4 1.2(6) . .
C5 O2 C4 O3 0.1(7) . .
C5 O2 C4 C3 -179.0(4) . .
C2 C3 C4 O3 -104.5(6) . .
C1 C3 C4 O3 73.6(6) 3_755 .
C2 C3 C4 O2 74.6(5) . .
C1 C3 C4 O2 -107.3(5) 3_755 .
C4 O2 C5 C6 -100.7(6) . .
C7 C8 C9 C7 -0.9(7) 3_745 .
Br2 C8 C9 C7 176.9(3) . .
C7 C8 C9 C10 -179.1(4) 3_745 .
Br2 C8 C9 C10 -1.4(6) . .
O4 C7 C9 C8 178.1(4) . .
C8 C7 C9 C8 0.8(7) 3_745 .
O4 C7 C9 C10 -3.6(6) . .
C8 C7 C9 C10 179.2(4) 3_745 .
C11 O6 C10 O5 -3.6(6) . .
C11 O6 C10 C9 178.1(4) . .
C8 C9 C10 O5 103.2(6) . .
C7 C9 C10 O5 -75.1(6) . .
C8 C9 C10 O6 -78.4(5) . .
C7 C9 C10 O6 103.3(5) . .
C10 O6 C11 C12 -86.7(5) . .
