#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/60/1516085.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_1516085
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         'C26 H24 O8'
_chemical_formula_sum            'C26 H24 O8'
_chemical_formula_weight         464.45
_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                 94.765(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.2710(5)
_cell_length_b                   14.1093(14)
_cell_length_c                   15.2301(17)
_cell_measurement_reflns_used    1813
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5408
_cell_measurement_theta_min      2.8816
_cell_volume                     1128.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.867
_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  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8990
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Tue Aug 09 06:00:07 2011'
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.4146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                1771
_reflns_number_total             2502
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            2b.CIF
_cod_data_source_block           acb159_2b
_cod_database_code               1516085
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
O1 O -0.2432(3) 0.55629(10) 0.85031(10) 0.0303(4) Uani 1 1 d .
O2 O 0.1112(3) 0.43041(10) 0.83821(10) 0.0287(4) Uani 1 1 d .
O3 O 0.5943(3) 0.36088(10) 0.97308(11) 0.0302(4) Uani 1 1 d .
O4 O 0.3190(3) 0.27291(10) 1.04280(10) 0.0260(4) Uani 1 1 d .
C1 C -0.1286(4) 0.53364(14) 0.91993(14) 0.0223(5) Uani 1 1 d .
C2 C 0.0724(4) 0.45759(13) 0.92050(13) 0.0212(5) Uani 1 1 d .
C3 C 0.1868(4) 0.42493(13) 0.99652(14) 0.0201(4) Uani 1 1 d .
C4 C 0.3906(4) 0.35055(14) 1.00186(13) 0.0216(5) Uani 1 1 d .
C5 C 0.1882(4) 0.33726(15) 0.82081(14) 0.0253(5) Uani 1 1 d .
C6 C 0.0550(4) 0.26141(15) 0.84991(14) 0.0258(5) Uani 1 1 d .
H6A H -0.0823 0.2714 0.8855 0.031 Uiso 1 1 calc R
C7 C 0.1220(4) 0.16987(15) 0.82705(14) 0.0275(5) Uani 1 1 d .
C8 C 0.3203(5) 0.15861(16) 0.77304(15) 0.0317(5) Uani 1 1 d .
H8A H 0.3670 0.0967 0.7559 0.038 Uiso 1 1 calc R
C9 C 0.4501(5) 0.23579(16) 0.74394(16) 0.0323(5) Uani 1 1 d .
H9A H 0.5846 0.2265 0.7070 0.039 Uiso 1 1 calc R
C10 C 0.3859(4) 0.32662(16) 0.76817(15) 0.0297(5) Uani 1 1 d .
H10A H 0.4758 0.3801 0.7490 0.036 Uiso 1 1 calc R
C11 C -0.0179(5) 0.08594(16) 0.85856(16) 0.0351(6) Uani 1 1 d .
H11A H 0.1034 0.0350 0.8748 0.053 Uiso 1 1 calc R
H11B H -0.1420 0.0639 0.8115 0.053 Uiso 1 1 calc R
H11C H -0.1067 0.1039 0.9101 0.053 Uiso 1 1 calc R
C12 C 0.5007(5) 0.19535(15) 1.04545(17) 0.0332(6) Uani 1 1 d .
H12A H 0.6642 0.2151 1.0769 0.040 Uiso 1 1 calc R
H12B H 0.5330 0.1759 0.9849 0.040 Uiso 1 1 calc R
C13 C 0.3867(5) 0.11501(17) 1.09299(19) 0.0433(7) Uani 1 1 d .
H13A H 0.4998 0.0599 1.0931 0.065 Uiso 1 1 calc R
H13B H 0.2206 0.0986 1.0632 0.065 Uiso 1 1 calc R
H13C H 0.3652 0.1340 1.1538 0.065 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'
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
C2 O2 C5 120.75(16) . .
C4 O4 C12 114.90(16) . .
O1 C1 C2 119.28(19) . .
O1 C1 C3 121.98(19) . 3_567
C2 C1 C3 118.69(18) . 3_567
O2 C2 C1 111.07(17) . .
O2 C2 C3 127.95(19) . .
C1 C2 C3 120.98(18) . .
C1 C3 C2 120.25(18) 3_567 .
C1 C3 C4 115.84(18) 3_567 .
C2 C3 C4 123.77(18) . .
O3 C4 O4 124.58(18) . .
O3 C4 C3 123.59(18) . .
O4 C4 C3 111.82(17) . .
O2 C5 C6 120.26(19) . .
O2 C5 C10 117.14(19) . .
C6 C5 C10 122.39(19) . .
C5 C6 H6A 120.2 . .
C5 C6 C7 119.7(2) . .
H6A C6 C7 120.2 . .
C6 C7 C8 118.2(2) . .
C6 C7 C11 120.9(2) . .
C8 C7 C11 120.93(19) . .
C7 C8 H8A 119.4 . .
C7 C8 C9 121.1(2) . .
H8A C8 C9 119.4 . .
C8 C9 H9A 119.8 . .
C8 C9 C10 120.5(2) . .
H9A C9 C10 119.8 . .
C5 C10 C9 118.1(2) . .
C5 C10 H10A 121.0 . .
C9 C10 H10A 121.0 . .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 . .
C7 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O4 C12 H12A 110.3 . .
O4 C12 H12B 110.3 . .
O4 C12 C13 107.06(19) . .
H12A C12 H12B 108.6 . .
H12A C12 C13 110.3 . .
H12B C12 C13 110.3 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.219(3) .
O2 C2 1.342(3) .
O2 C5 1.407(2) .
O3 C4 1.202(2) .
O4 C4 1.331(2) .
O4 C12 1.453(2) .
C1 C2 1.507(3) .
C1 C3 1.456(3) 3_567
C2 C3 1.342(3) .
C3 C1 1.456(3) 3_567
C3 C4 1.499(3) .
C5 C6 1.374(3) .
C5 C10 1.375(3) .
C6 H6A 0.950 .
C6 C7 1.391(3) .
C7 C8 1.392(3) .
C7 C11 1.495(3) .
C8 H8A 0.950 .
C8 C9 1.379(3) .
C9 H9A 0.950 .
C9 C10 1.383(3) .
C10 H10A 0.950 .
C11 H11A 0.980 .
C11 H11B 0.980 .
C11 H11C 0.980 .
C12 H12A 0.990 .
C12 H12B 0.990 .
C12 C13 1.497(3) .
C13 H13A 0.980 .
C13 H13B 0.980 .
C13 H13C 0.980 .
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
C5 O2 C2 C1 -149.85(18) . .
C5 O2 C2 C3 29.7(3) . .
O1 C1 C2 O2 5.5(3) . .
O1 C1 C2 C3 -174.11(19) . .
C3 C1 C2 O2 -177.03(17) 3_567 .
C3 C1 C2 C3 3.4(3) 3_567 .
O2 C2 C3 C1 177.05(18) . 3_567
O2 C2 C3 C4 1.4(3) . .
C1 C2 C3 C1 -3.4(3) . 3_567
C1 C2 C3 C4 -179.05(18) . .
C12 O4 C4 O3 -4.4(3) . .
C12 O4 C4 C3 176.22(18) . .
C1 C3 C4 O3 -112.6(2) 3_567 .
C1 C3 C4 O4 66.8(2) 3_567 .
C2 C3 C4 O3 63.2(3) . .
C2 C3 C4 O4 -117.4(2) . .
C2 O2 C5 C6 51.9(3) . .
C2 O2 C5 C10 -133.2(2) . .
O2 C5 C6 C7 175.51(19) . .
C10 C5 C6 C7 0.9(3) . .
C5 C6 C7 C8 -1.5(3) . .
C5 C6 C7 C11 179.4(2) . .
C6 C7 C8 C9 1.0(3) . .
C11 C7 C8 C9 -179.9(2) . .
C7 C8 C9 C10 0.1(3) . .
O2 C5 C10 C9 -174.5(2) . .
C6 C5 C10 C9 0.2(3) . .
C8 C9 C10 C5 -0.8(3) . .
C4 O4 C12 C13 -179.57(19) . .
