#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/60/1516094.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_1516094
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         'C32 H26 O8'
_chemical_formula_sum            'C32 H26 O8'
_chemical_formula_weight         538.53
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.533(11)
_cell_angle_beta                 80.008(10)
_cell_angle_gamma                86.414(9)
_cell_formula_units_Z            1
_cell_length_a                   6.1693(7)
_cell_length_b                   9.7194(11)
_cell_length_c                   11.3573(13)
_cell_measurement_reflns_used    850
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.4611
_cell_measurement_theta_min      3.3464
_cell_volume                     619.77(13)
_computing_cell_refinement
;
'Wed Sep 21 15:54:19 2011'
;
_computing_data_collection
;
'Wed Sep 21 15:54:19 2011'
;
_computing_data_reduction
;
'Wed Sep 21 15:54:19 2011'
;
_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 0.809
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4481
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Wed Sep 21 15:54:19 2011'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0555
_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)+(0.0402P)²+0.0355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1693
_reflns_number_total             2543
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            3d.CIF
_cod_data_source_block           acb169_3d
_cod_original_cell_volume        619.77(12)
_cod_database_code               1516094
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.5761(2) 0.80070(17) 0.43495(14) 0.0262(4) Uani 1 1 d .
O2 O 0.7894(2) 0.92226(19) 0.24744(15) 0.0309(4) Uani 1 1 d .
O3 O 0.5962(2) 0.87363(16) 0.63196(14) 0.0223(4) Uani 1 1 d .
O4 O 0.8601(2) 0.95000(18) 0.75640(14) 0.0277(4) Uani 1 1 d .
H4 H 0.971(5) 0.993(3) 0.787(3) 0.068(10) Uiso 1 1 d .
C1 C 0.2742(4) 0.6454(3) 0.4675(2) 0.0347(6) Uani 1 1 d .
H1A H 0.1921 0.5956 0.4285 0.052 Uiso 1 1 calc R
H1B H 0.1742 0.7089 0.5014 0.052 Uiso 1 1 calc R
H1C H 0.3388 0.5705 0.5381 0.052 Uiso 1 1 calc R
C2 C 0.4537(4) 0.7391(3) 0.3674(2) 0.0284(6) Uani 1 1 d .
H2A H 0.5510 0.6778 0.3282 0.034 Uiso 1 1 calc R
H2B H 0.3908 0.8199 0.2983 0.034 Uiso 1 1 calc R
C3 C 0.7391(3) 0.8920(3) 0.3637(2) 0.0230(5) Uani 1 1 d .
C4 C 0.8653(3) 0.9492(2) 0.4356(2) 0.0212(5) Uani 1 1 d .
C5 C 0.8021(3) 0.9280(2) 0.5662(2) 0.0200(5) Uani 1 1 d .
C6 C 0.9356(3) 0.9761(2) 0.6302(2) 0.0204(5) Uani 1 1 d .
C7 C 0.5706(3) 0.7252(2) 0.7134(2) 0.0210(5) Uani 1 1 d .
C8 C 0.3548(3) 0.6881(3) 0.7792(2) 0.0238(5) Uani 1 1 d .
H8 H 0.2432 0.7619 0.7660 0.029 Uiso 1 1 calc R
C9 C 0.3069(4) 0.5453(3) 0.8621(2) 0.0265(6) Uani 1 1 d .
H9 H 0.1608 0.5204 0.9066 0.032 Uiso 1 1 calc R
C10 C 0.4697(4) 0.4335(3) 0.8832(2) 0.0236(5) Uani 1 1 d .
C11 C 0.4248(4) 0.2853(3) 0.9705(2) 0.0295(6) Uani 1 1 d .
H11 H 0.2796 0.2581 1.0157 0.035 Uiso 1 1 calc R
C12 C 0.5865(4) 0.1812(3) 0.9908(2) 0.0334(6) Uani 1 1 d .
H12 H 0.5543 0.0825 1.0511 0.040 Uiso 1 1 calc R
C13 C 0.8007(4) 0.2190(3) 0.9230(2) 0.0328(6) Uani 1 1 d .
H13 H 0.9128 0.1456 0.9374 0.039 Uiso 1 1 calc R
C14 C 0.8497(4) 0.3613(3) 0.8359(2) 0.0282(6) Uani 1 1 d .
H14 H 0.9949 0.3850 0.7893 0.034 Uiso 1 1 calc R
C15 C 0.6867(3) 0.4728(3) 0.8148(2) 0.0227(5) Uani 1 1 d .
C16 C 0.7337(3) 0.6227(2) 0.7292(2) 0.0228(5) Uani 1 1 d .
H16 H 0.8784 0.6507 0.6834 0.027 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 O1 C3 116.35(17) . .
C5 O3 C7 119.84(15) . .
H4 O4 C6 106.9(17) . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1A C1 C2 109.5 . .
H1B C1 H1C 109.5 . .
H1B C1 C2 109.5 . .
H1C C1 C2 109.5 . .
O1 C2 C1 105.93(18) . .
O1 C2 H2A 110.5 . .
O1 C2 H2B 110.5 . .
C1 C2 H2A 110.5 . .
C1 C2 H2B 110.5 . .
H2A C2 H2B 108.7 . .
O1 C3 O2 122.4(2) . .
O1 C3 C4 115.18(19) . .
O2 C3 C4 122.3(2) . .
C3 C4 C5 124.0(2) . .
C3 C4 C6 117.70(19) . 2_776
C5 C4 C6 118.2(2) . 2_776
O3 C5 C4 121.3(2) . .
O3 C5 C6 117.26(19) . .
C4 C5 C6 121.1(2) . .
O4 C6 C4 122.8(2) . 2_776
O4 C6 C5 116.55(19) . .
C4 C6 C5 120.65(19) 2_776 .
O3 C7 C8 113.41(18) . .
O3 C7 C16 124.66(19) . .
C8 C7 C16 121.9(2) . .
C7 C8 H8 120.3 . .
C7 C8 C9 119.4(2) . .
H8 C8 C9 120.3 . .
C8 C9 H9 119.3 . .
C8 C9 C10 121.5(2) . .
H9 C9 C10 119.3 . .
C9 C10 C11 122.5(2) . .
C9 C10 C15 118.4(2) . .
C11 C10 C15 119.2(2) . .
C10 C11 H11 119.5 . .
C10 C11 C12 121.0(2) . .
H11 C11 C12 119.5 . .
C11 C12 H12 119.9 . .
C11 C12 C13 120.1(2) . .
H12 C12 C13 119.9 . .
C12 C13 H13 119.7 . .
C12 C13 C14 120.5(2) . .
H13 C13 C14 119.7 . .
C13 C14 H14 119.7 . .
C13 C14 C15 120.6(2) . .
H14 C14 C15 119.7 . .
C10 C15 C14 118.5(2) . .
C10 C15 C16 119.3(2) . .
C14 C15 C16 122.1(2) . .
C7 C16 C15 119.5(2) . .
C7 C16 H16 120.2 . .
C15 C16 H16 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.457(3) .
O1 C3 1.317(3) .
O2 C3 1.224(2) .
O3 C5 1.380(2) .
O3 C7 1.386(2) .
O4 H4 1.00(3) .
O4 C6 1.357(2) .
C1 H1A 0.980 .
C1 H1B 0.980 .
C1 H1C 0.980 .
C1 C2 1.499(3) .
C2 H2A 0.990 .
C2 H2B 0.990 .
C3 C4 1.484(3) .
C4 C5 1.404(3) .
C4 C6 1.404(3) 2_776
C5 C6 1.393(3) .
C6 C4 1.404(3) 2_776
C7 C8 1.403(3) .
C7 C16 1.356(3) .
C8 H8 0.950 .
C8 C9 1.362(3) .
C9 H9 0.950 .
C9 C10 1.413(3) .
C10 C11 1.413(3) .
C10 C15 1.421(3) .
C11 H11 0.950 .
C11 C12 1.359(3) .
C12 H12 0.950 .
C12 C13 1.402(3) .
C13 H13 0.950 .
C13 C14 1.373(3) .
C14 H14 0.950 .
C14 C15 1.411(3) .
C15 C16 1.423(3) .
C16 H16 0.950 .
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
O4 H4 O2 1.00(3) 1.65(3) 2.546(2) 147(3) 2_776
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
C3 O1 C2 C1 -177.71(18) . .
C2 O1 C3 O2 -1.3(3) . .
C2 O1 C3 C4 -178.11(16) . .
O1 C3 C4 C5 -9.0(3) . .
O1 C3 C4 C6 168.37(18) . 2_776
O2 C3 C4 C5 174.2(2) . .
O2 C3 C4 C6 -8.4(3) . 2_776
C7 O3 C5 C4 100.9(2) . .
C7 O3 C5 C6 -85.9(2) . .
C3 C4 C5 O3 -11.3(3) . .
C3 C4 C5 C6 175.75(19) . .
C6 C4 C5 O3 171.27(17) 2_776 .
C6 C4 C5 C6 -1.7(3) 2_776 .
O3 C5 C6 O4 7.0(3) . .
O3 C5 C6 C4 -171.51(17) . 2_776
C4 C5 C6 O4 -179.80(18) . .
C4 C5 C6 C4 1.7(3) . 2_776
C5 O3 C7 C8 176.57(18) . .
C5 O3 C7 C16 -4.2(3) . .
O3 C7 C8 C9 179.72(19) . .
C16 C7 C8 C9 0.4(3) . .
C7 C8 C9 C10 -0.1(3) . .
C8 C9 C10 C11 178.8(2) . .
C8 C9 C10 C15 -0.5(3) . .
C9 C10 C11 C12 -178.5(2) . .
C15 C10 C11 C12 0.8(3) . .
C10 C11 C12 C13 -1.2(3) . .
C11 C12 C13 C14 0.2(4) . .
C12 C13 C14 C15 1.2(3) . .
C13 C14 C15 C10 -1.6(3) . .
C13 C14 C15 C16 177.4(2) . .
C9 C10 C15 C14 179.93(19) . .
C9 C10 C15 C16 0.9(3) . .
C11 C10 C15 C14 0.6(3) . .
C11 C10 C15 C16 -178.5(2) . .
O3 C7 C16 C15 -179.29(19) . .
C8 C7 C16 C15 -0.1(3) . .
C10 C15 C16 C7 -0.6(3) . .
C14 C15 C16 C7 -179.61(19) . .
