#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/60/1516090.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_1516090
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 H26 O8'
_chemical_formula_sum            'C26 H26 O8'
_chemical_formula_weight         466.47
_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                 97.280(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7228(5)
_cell_length_b                   11.0389(6)
_cell_length_c                   13.6925(9)
_cell_measurement_reflns_used    2132
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5430
_cell_measurement_theta_min      2.9935
_cell_volume                     1157.89(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.827
_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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6328
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.61
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Thu Jun 23 11:05:27 2011'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0395
_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)+(0.0431P)²+0.2924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                1929
_reflns_number_total             2451
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            3c.CIF
_cod_data_source_block           acb145_3c
_cod_database_code               1516090
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 -0.26686(12) 0.57438(9) 0.69542(7) 0.0304(3) Uani 1 1 d .
O2 O -0.40217(14) 0.42688(10) 0.60508(8) 0.0376(3) Uani 1 1 d .
O3 O -0.28768(13) 0.35720(9) 0.44766(8) 0.0308(3) Uani 1 1 d .
H3 H -0.356(3) 0.3647(19) 0.4965(16) 0.065(6) Uiso 1 1 d .
O4 O 0.04344(12) 0.64215(8) 0.66717(7) 0.0248(2) Uani 1 1 d .
C1 C -0.3868(2) 0.68700(16) 0.81805(12) 0.0419(4) Uani 1 1 d .
H1A H -0.4779 0.6900 0.8618 0.063 Uiso 1 1 calc R
H1B H -0.3954 0.7589 0.7757 0.063 Uiso 1 1 calc R
H1C H -0.2718 0.6850 0.8576 0.063 Uiso 1 1 calc R
C2 C -0.41013(19) 0.57596(16) 0.75574(11) 0.0353(4) Uani 1 1 d .
H2A H -0.4063 0.5026 0.7976 0.042 Uiso 1 1 calc R
H2B H -0.5239 0.5783 0.7134 0.042 Uiso 1 1 calc R
C3 C -0.27890(18) 0.49589(13) 0.62306(10) 0.0257(3) Uani 1 1 d .
C4 C -0.13208(17) 0.49903(12) 0.56249(10) 0.0234(3) Uani 1 1 d .
C5 C 0.01851(18) 0.56922(12) 0.58505(10) 0.0229(3) Uani 1 1 d .
C6 C -0.14826(17) 0.42845(12) 0.47616(10) 0.0238(3) Uani 1 1 d .
C7 C 0.11002(16) 0.58795(12) 0.75570(10) 0.0229(3) Uani 1 1 d .
C8 C 0.16896(18) 0.46995(13) 0.76243(11) 0.0276(3) Uani 1 1 d .
H8A H 0.1644 0.4204 0.7054 0.033 Uiso 1 1 calc R
C9 C 0.2351(2) 0.42527(14) 0.85424(12) 0.0359(4) Uani 1 1 d .
H9A H 0.2768 0.3443 0.8603 0.043 Uiso 1 1 calc R
C10 C 0.2408(2) 0.49708(15) 0.93677(11) 0.0368(4) Uani 1 1 d .
H10A H 0.2863 0.4651 0.9992 0.044 Uiso 1 1 calc R
C11 C 0.18057(18) 0.61598(14) 0.92992(11) 0.0307(3) Uani 1 1 d .
C12 C 0.11521(17) 0.66096(13) 0.83812(10) 0.0259(3) Uani 1 1 d .
H12A H 0.0739 0.7420 0.8318 0.031 Uiso 1 1 calc R
C13 C 0.1849(2) 0.69384(17) 1.02049(12) 0.0445(4) Uani 1 1 d .
H13A H 0.1656 0.7787 1.0009 0.067 Uiso 1 1 calc R
H13B H 0.2989 0.6859 1.0605 0.067 Uiso 1 1 calc R
H13C H 0.0930 0.6677 1.0590 0.067 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_3
C2 O1 C3 116.66(11) .
H3 O3 C6 104.6(13) .
C5 O4 C7 117.29(10) .
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 106.73(12) .
O1 C2 H2A 110.4 .
O1 C2 H2B 110.4 .
C1 C2 H2A 110.4 .
C1 C2 H2B 110.4 .
H2A C2 H2B 108.6 .
O1 C3 O2 122.97(13) .
O1 C3 C4 114.83(12) .
O2 C3 C4 122.18(13) .
C3 C4 C5 124.12(12) .
C3 C4 C6 117.53(12) .
C5 C4 C6 118.34(12) .
O4 C5 C4 122.05(12) .
O4 C5 C6 116.50(11) 3_566
C4 C5 C6 121.43(12) 3_566
O3 C6 C4 123.20(13) .
O3 C6 C5 116.56(12) 3_566
C4 C6 C5 120.23(12) 3_566
O4 C7 C8 123.17(12) .
O4 C7 C12 115.45(12) .
C8 C7 C12 121.38(13) .
C7 C8 H8A 120.7 .
C7 C8 C9 118.50(14) .
H8A C8 C9 120.7 .
C8 C9 H9A 119.7 .
C8 C9 C10 120.62(14) .
H9A C9 C10 119.7 .
C9 C10 H10A 119.6 .
C9 C10 C11 120.81(14) .
H10A C10 C11 119.6 .
C10 C11 C12 118.64(14) .
C10 C11 C13 120.69(14) .
C12 C11 C13 120.67(14) .
C7 C12 C11 120.05(13) .
C7 C12 H12A 120.0 .
C11 C12 H12A 120.0 .
C11 C13 H13A 109.5 .
C11 C13 H13B 109.5 .
C11 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 C2 1.4622(17) .
O1 C3 1.3106(17) .
O2 C3 1.2198(17) .
O3 H3 0.91(2) .
O3 C6 1.3504(16) .
O4 C5 1.3764(16) .
O4 C7 1.3906(16) .
C1 H1A 0.980 .
C1 H1B 0.980 .
C1 H1C 0.980 .
C1 C2 1.491(2) .
C2 H2A 0.990 .
C2 H2B 0.990 .
C3 C4 1.488(2) .
C4 C5 1.3990(19) .
C4 C6 1.4081(19) .
C5 C6 1.3856(19) 3_566
C6 C5 1.3857(19) 3_566
C7 C8 1.379(2) .
C7 C12 1.3832(19) .
C8 H8A 0.950 .
C8 C9 1.386(2) .
C9 H9A 0.950 .
C9 C10 1.376(2) .
C10 H10A 0.950 .
C10 C11 1.392(2) .
C11 C12 1.386(2) .
C11 C13 1.506(2) .
C12 H12A 0.950 .
C13 H13A 0.980 .
C13 H13B 0.980 .
C13 H13C 0.980 .
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
O3 H3 O2 0.91(2) 1.71(2) 2.5501(15) 152(2)
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_4
C3 O1 C2 C1 -168.47(12) .
C2 O1 C3 O2 0.2(2) .
C2 O1 C3 C4 178.88(12) .
O1 C3 C4 C5 6.89(19) .
O1 C3 C4 C6 -171.84(11) .
O2 C3 C4 C5 -174.45(13) .
O2 C3 C4 C6 6.8(2) .
C7 O4 C5 C4 83.61(15) .
C7 O4 C5 C6 -98.31(14) 3_566
C3 C4 C5 O4 0.3(2) .
C3 C4 C5 C6 -177.72(12) 3_566
C6 C4 C5 O4 179.00(11) .
C6 C4 C5 C6 1.0(2) 3_566
C3 C4 C6 O3 -1.42(19) .
C3 C4 C6 C5 177.82(12) 3_566
C5 C4 C6 O3 179.77(12) .
C5 C4 C6 C5 -1.0(2) 3_566
C5 O4 C7 C8 7.34(18) .
C5 O4 C7 C12 -173.21(11) .
O4 C7 C8 C9 179.14(12) .
C12 C7 C8 C9 -0.3(2) .
C7 C8 C9 C10 0.3(2) .
C8 C9 C10 C11 -0.1(2) .
C9 C10 C11 C12 -0.2(2) .
C9 C10 C11 C13 179.24(15) .
O4 C7 C12 C11 -179.48(12) .
C8 C7 C12 C11 0.0(2) .
C10 C11 C12 C7 0.3(2) .
C13 C11 C12 C7 -179.20(13) .
