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#$Date: 2019-10-14 11:49:59 +0200 (Mon 14 de Oct de 2019) $
#$Revision: 219334 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/45/7234595.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_7234595
loop_
_publ_author_name
'Xiaoqin Shen'
'Yonghao Zheng'
'Fred Wudl'
_publ_section_title
;
 Thermally induced reversible solid-state transformation of novel
 s-indacene 1,3,5,7-tetraone derivatives
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2427
_journal_page_last               2431
_journal_paper_doi               10.1039/C5TC03953C
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C34 H34 O6 S2'
_chemical_formula_weight         602.73
_chemical_name_common            'DTID-Hep2 Form 2'
_chemical_name_systematic
'2,6-di(thiophen-2-yl)-s-indacene-1,5-dione-3,7-diyl diheptanoate'
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 124.840(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   31.156(5)
_cell_length_b                   6.3506(9)
_cell_length_c                   18.772(3)
_cell_measurement_temperature    100(2)
_cell_volume                     3048.4(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'Omega scan'
_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  0.0796
_diffrn_reflns_av_sigmaI/netI    0.0896
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11356
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'black brown'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.0808
_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)+(0.1066P)²+10.4282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2027
_refine_ls_wR_factor_ref         0.2390
_reflns_number_gt                2059
_reflns_number_total             3758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-2427.cif
_cod_data_source_block           2
_cod_original_cell_volume        3048.4(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7234595
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0877(2) 1.4587(8) 0.2572(3) 0.0417(11) Uani 1 1 d . . .
C2 C 1.1316(2) 1.4090(8) 0.2624(3) 0.0439(12) Uani 1 1 d . . .
C4 C 1.07374(16) 1.1351(7) 0.1773(2) 0.0292(9) Uani 1 1 d . . .
C5 C 1.05140(15) 0.9477(6) 0.1249(2) 0.0261(8) Uani 1 1 d . . .
C6 C 1.08103(15) 0.7924(6) 0.1075(2) 0.0272(8) Uani 1 1 d . . .
C7 C 1.04238(15) 0.6247(6) 0.0509(2) 0.0266(8) Uani 1 1 d . . .
C8 C 0.99429(15) 0.6786(6) 0.0348(2) 0.0246(8) Uani 1 1 d . . .
C9 C 1.00173(15) 0.8772(6) 0.0803(2) 0.0248(8) Uani 1 1 d . . .
C10 C 0.95022(16) 0.5534(6) -0.0173(2) 0.0255(8) Uani 1 1 d . . .
C11 C 0.93218(16) 0.9043(7) 0.0966(2) 0.0327(10) Uani 1 1 d . . .
C12 C 0.88450(17) 1.0339(8) 0.0676(3) 0.0376(11) Uani 1 1 d D . .
C13 C 0.84818(18) 0.9234(8) 0.0843(3) 0.0499(13) Uani 1 1 d D . .
C3A C 1.13060(11) 1.2125(4) 0.21754(15) 0.0372(4) Uani 0.772(3) 1 d P . .
C14A C 0.8234(3) 0.7347(13) 0.0249(5) 0.0425(16) Uani 0.457(5) 1 d PD . .
C15A C 0.7964(4) 0.7658(17) -0.0709(5) 0.055(2) Uani 0.457(5) 1 d PD . .
C16A C 0.7779(6) 0.541(2) -0.1136(7) 0.078(3) Uani 0.457(5) 1 d PD . .
C17A C 0.7566(5) 0.570(3) -0.2097(7) 0.089(4) Uani 0.457(5) 1 d PD . .
C14B C 0.8026(3) 1.0416(13) 0.0654(5) 0.0425(16) Uani 0.543(5) 1 d PD . .
C15B C 0.7755(3) 0.9252(15) 0.1026(6) 0.055(2) Uani 0.543(5) 1 d PD . .
C16B C 0.7305(4) 1.0587(19) 0.0868(9) 0.078(3) Uani 0.543(5) 1 d PD . .
C17B C 0.7056(5) 0.949(2) 0.1268(9) 0.089(4) Uani 0.543(5) 1 d PD . .
H1 H 1.079(2) 1.580(9) 0.279(3) 0.059(15) Uiso 1 1 d . . .
H2 H 1.1627(19) 1.480(8) 0.289(3) 0.048(14) Uiso 1 1 d . . .
H10 H 0.9185(16) 0.591(6) -0.030(2) 0.022(10) Uiso 1 1 d . . .
H12A H 0.869(2) 1.068(9) 0.007(4) 0.063(16) Uiso 1 1 d . . .
H12B H 0.899(2) 1.169(9) 0.094(4) 0.062(17) Uiso 1 1 d . . .
O1 O 1.12625(11) 0.8042(5) 0.13227(17) 0.0343(7) Uani 1 1 d . . .
O2 O 0.96057(10) 0.9921(4) 0.06819(16) 0.0293(7) Uani 1 1 d . . .
O3 O 0.94618(13) 0.7448(6) 0.1379(2) 0.0530(10) Uani 1 1 d . . .
S1A S 1.03916(6) 1.2919(2) 0.19999(8) 0.0372(4) Uani 0.772(3) 1 d P . .
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'
S S 0.1246 0.1234 '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 C1 C3B 114.4(4) . .
C2 C1 H1 132(3) . .
C3B C1 H1 114(3) . .
C1 C2 C3A 117.4(4) . .
C1 C2 H2 129(3) . .
C3A C2 H2 113(3) . .
C5 C4 C3A 124.3(3) . .
C5 C4 C3B 121.9(3) . .
C3A C4 C3B 113.8(3) . .
C9 C5 C4 129.2(4) . .
C9 C5 C6 106.0(3) . .
C4 C5 C6 124.7(3) . .
O1 C6 C7 127.2(4) . .
O1 C6 C5 126.8(4) . .
C7 C6 C5 105.9(3) . .
C10 C7 C8 122.9(4) 5_765 .
C10 C7 C6 129.1(4) 5_765 .
C8 C7 C6 108.0(3) . .
C10 C8 C7 121.3(4) . .
C10 C8 C9 131.7(4) . .
C7 C8 C9 107.0(3) . .
C5 C9 O2 123.9(4) . .
C5 C9 C8 113.0(3) . .
O2 C9 C8 122.5(3) . .
C7 C10 C8 115.8(4) 5_765 .
C7 C10 H10 123(3) 5_765 .
C8 C10 H10 121(3) . .
O3 C11 O2 120.9(4) . .
O3 C11 C12 128.1(4) . .
O2 C11 C12 110.9(4) . .
C11 C12 C13 111.9(4) . .
C11 C12 H12A 105(3) . .
C13 C12 H12A 115(3) . .
C11 C12 H12B 103(3) . .
C13 C12 H12B 119(3) . .
H12A C12 H12B 100(4) . .
C14B C13 C14A 102.2(6) . .
C14B C13 C12 116.9(5) . .
C14A C13 C12 110.0(4) . .
C2 C3A C4 100.8(3) . .
C13 C14A C15A 118.6(6) . .
C14A C15A C16A 106.4(7) . .
C14A C15A C17B 115.6(9) . 7_665
C16A C15A C17B 24.0(6) . 7_665
C17B C16A C16B 138(3) 7_665 7_665
C17B C16A C17A 58.5(16) 7_665 .
C16B C16A C17A 130.3(14) 7_665 .
C17B C16A C15A 88.3(18) 7_665 .
C16B C16A C15A 118.5(12) 7_665 .
C17A C16A C15A 106.0(8) . .
C17B C16A C15B 163(2) 7_665 7_665
C16B C16A C15B 57.3(10) 7_665 7_665
C17A C16A C15B 108.4(10) . 7_665
C15A C16A C15B 86.0(8) . 7_665
C17B C17A C16A 26.6(6) 7_665 .
C1 C3B C4 93.6(2) . .
C13 C14B C15B 110.4(6) . .
C16B C15B C14B 109.0(7) . .
C16B C15B C16A 31.2(6) . 7_665
C14B C15B C16A 140.2(8) . 7_665
C16A C16B C15B 91.5(14) 7_665 .
C16A C16B C17B 17.6(12) 7_665 .
C15B C16B C17B 108.9(8) . .
C16A C17B C17A 95.0(18) 7_665 7_665
C16A C17B C16B 24.1(17) 7_665 .
C17A C17B C16B 105.3(11) 7_665 .
C16A C17B C15A 67.8(15) 7_665 7_665
C17A C17B C15A 110.4(13) 7_665 7_665
C16B C17B C15A 85.0(8) . 7_665
C11 O2 C9 117.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.348(7) .
C1 C3B 1.646(5) .
C1 H1 0.98(6) .
C2 C3A 1.497(6) .
C2 H2 0.92(5) .
C4 C5 1.444(5) .
C4 C3A 1.556(5) .
C4 C3B 1.691(4) .
C5 C9 1.347(5) .
C5 C6 1.509(6) .
C6 O1 1.207(5) .
C6 C7 1.500(5) .
C7 C10 1.377(6) 5_765
C7 C8 1.391(5) .
C8 C10 1.393(5) .
C8 C9 1.466(5) .
C9 O2 1.377(5) .
C10 C7 1.377(6) 5_765
C10 H10 0.91(4) .
C11 O3 1.197(5) .
C11 O2 1.384(5) .
C11 C12 1.502(6) .
C12 C13 1.509(6) .
C12 H12A 0.97(6) .
C12 H12B 0.96(6) .
C13 C14B 1.460(7) .
C13 C14A 1.514(7) .
C14A C15A 1.502(8) .
C15A C16A 1.574(9) .
C15A C17B 1.700(18) 7_665
C16A C17B 0.691(14) 7_665
C16A C16B 0.934(16) 7_665
C16A C17A 1.538(10) .
C16A C15B 1.802(16) 7_665
C17A C17B 1.316(19) 7_665
C14B C15B 1.553(8) .
C15B C16B 1.517(9) .
C15B C16A 1.802(16) 7_665
C16B C16A 0.934(16) 7_665
C16B C17B 1.521(9) .
C17B C16A 0.691(14) 7_665
C17B C17A 1.316(19) 7_665
C17B C15A 1.700(18) 7_665
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3B C1 C2 C3A -0.5(5) . . . .
C3A C4 C5 C9 -172.9(3) . . . .
C3B C4 C5 C9 7.0(5) . . . .
C3A C4 C5 C6 4.8(5) . . . .
C3B C4 C5 C6 -175.3(3) . . . .
C9 C5 C6 O1 176.2(4) . . . .
C4 C5 C6 O1 -2.0(6) . . . .
C9 C5 C6 C7 -2.1(4) . . . .
C4 C5 C6 C7 179.8(3) . . . .
O1 C6 C7 C10 2.2(6) . . . 5_765
C5 C6 C7 C10 -179.6(3) . . . 5_765
O1 C6 C7 C8 -176.9(4) . . . .
C5 C6 C7 C8 1.4(4) . . . .
C10 C7 C8 C10 -0.1(6) 5_765 . . .
C6 C7 C8 C10 179.1(3) . . . .
C10 C7 C8 C9 -179.3(3) 5_765 . . .
C6 C7 C8 C9 -0.2(4) . . . .
C4 C5 C9 O2 8.7(6) . . . .
C6 C5 C9 O2 -169.4(3) . . . .
C4 C5 C9 C8 -179.9(3) . . . .
C6 C5 C9 C8 2.1(4) . . . .
C10 C8 C9 C5 179.6(4) . . . .
C7 C8 C9 C5 -1.2(4) . . . .
C10 C8 C9 O2 -8.8(6) . . . .
C7 C8 C9 O2 170.4(3) . . . .
C7 C8 C10 C7 0.1(6) . . . 5_765
C9 C8 C10 C7 179.1(3) . . . 5_765
O3 C11 C12 C13 -9.1(6) . . . .
O2 C11 C12 C13 170.3(3) . . . .
C11 C12 C13 C14B 175.1(5) . . . .
C11 C12 C13 C14A -69.0(6) . . . .
C1 C2 C3A C4 0.7(5) . . . .
C5 C4 C3A C2 179.3(3) . . . .
C3B C4 C3A C2 -0.6(3) . . . .
C14B C13 C14A C15A 72.3(9) . . . .
C12 C13 C14A C15A -52.5(10) . . . .
C13 C14A C15A C16A 176.9(9) . . . .
C13 C14A C15A C17B 153.2(8) . . . 7_665
C14A C15A C16A C17B -117(2) . . . 7_665
C14A C15A C16A C16B 30(2) . . . 7_665
C17B C15A C16A C16B 146(3) 7_665 . . 7_665
C14A C15A C16A C17A -173.0(10) . . . .
C17B C15A C16A C17A -56.4(17) 7_665 . . .
C14A C15A C16A C15B 79.1(9) . . . 7_665
C17B C15A C16A C15B -164(2) 7_665 . . 7_665
C16B C16A C17A C17B -129(3) 7_665 . . 7_665
C15A C16A C17A C17B 78(2) . . . 7_665
C15B C16A C17A C17B 169(2) 7_665 . . 7_665
C2 C1 C3B C4 0.1(4) . . . .
C5 C4 C3B C1 -179.6(3) . . . .
C3A C4 C3B C1 0.3(3) . . . .
C14A C13 C14B C15B 71.0(7) . . . .
C12 C13 C14B C15B -168.9(5) . . . .
C13 C14B C15B C16B 176.5(7) . . . .
C13 C14B C15B C16A 176.4(9) . . . 7_665
C14B C15B C16B C16A -179.9(11) . . . 7_665
C14B C15B C16B C17B -177.5(10) . . . .
C16A C15B C16B C17B 2.4(9) 7_665 . . .
C15B C16B C17B C16A -8(3) . . . 7_665
C16A C16B C17B C17A 67(3) 7_665 . . 7_665
C15B C16B C17B C17A 59.0(15) . . . 7_665
C16A C16B C17B C15A -43(3) 7_665 . . 7_665
C15B C16B C17B C15A -50.8(10) . . . 7_665
O3 C11 O2 C9 7.4(5) . . . .
C12 C11 O2 C9 -172.0(3) . . . .
C5 C9 O2 C11 -122.5(4) . . . .
C8 C9 O2 C11 66.8(4) . . . .
