#------------------------------------------------------------------------------
#$Date: 2019-07-17 10:46:18 +0300 (Wed, 17 Jul 2019) $
#$Revision: 217114 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233182.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_7233182
loop_
_publ_author_name
'Chandrani Pramanik'
'Yushu Li'
'Anup Singh'
'Weimin Lin'
'Jennifer L. Hodgson'
'Jonathan B. Briggs'
'Simka Ellis'
'Peter Muller'
'Nicol E. McGruer'
'Glen P. Miller'
_publ_section_title
;
 Water soluble pentacene
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2193
_journal_page_last               2201
_journal_paper_doi               10.1039/C3TC00278K
_journal_volume                  1
_journal_year                    2013
_chemical_formula_moiety         'C28 H22 O4 S2, 2(C2 H4 O2)'
_chemical_formula_sum            'C32 H30 O8 S2'
_chemical_formula_weight         606.68
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.067(2)
_cell_angle_beta                 94.337(2)
_cell_angle_gamma                92.778(2)
_cell_formula_units_Z            1
_cell_length_a                   5.0554(4)
_cell_length_b                   10.5514(8)
_cell_length_c                   13.4788(10)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      2.27
_cell_volume                     704.49(9)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker Smart APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatech ImuS multilayer optics'
_diffrn_radiation_source         'ImuS micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25794
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.748
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.748
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0489
_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)+(0.1264P)²+1.4688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1669
_reflns_number_gt                3313
_reflns_number_total             4176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000001.cif
_cod_data_source_block           PCOD1000001
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7233182
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0118(4) 0.5044(2) 0.31925(16) 0.0273(4) Uani 1 1 d . . .
H1 H 1.0474 0.4157 0.3098 0.033 Uiso 1 1 calc R . .
C2 C 0.8374(4) 0.5508(2) 0.38687(16) 0.0260(4) Uani 1 1 d . . .
H2 H 0.7525 0.4943 0.4240 0.031 Uiso 1 1 calc R . .
C3 C 0.7814(4) 0.68378(18) 0.40225(14) 0.0213(4) Uani 1 1 d . . .
C4 C 0.6047(4) 0.73437(18) 0.47043(14) 0.0210(4) Uani 1 1 d . . .
H4 H 0.5164 0.6783 0.5071 0.025 Uiso 1 1 calc R . .
C5 C 0.5516(4) 0.86658(18) 0.48731(13) 0.0190(3) Uani 1 1 d . . .
C6 C 0.3777(4) 0.91820(18) 0.55918(13) 0.0190(3) Uani 1 1 d . . .
C7 C 0.3222(4) 1.04983(17) 0.57276(13) 0.0185(3) Uani 1 1 d . . .
C8 C 0.1482(4) 1.10463(19) 0.64307(14) 0.0217(4) Uani 1 1 d . . .
H8 H 0.0679 1.0513 0.6838 0.026 Uiso 1 1 calc R . .
C9 C 0.0896(4) 1.23257(19) 0.65515(14) 0.0207(3) Uani 1 1 d . . .
C10 C -0.0950(4) 1.2860(2) 0.72509(15) 0.0252(4) Uani 1 1 d . . .
H10 H -0.1848 1.2318 0.7628 0.030 Uiso 1 1 calc R . .
C11 C -0.1414(4) 1.4132(2) 0.73747(16) 0.0270(4) Uani 1 1 d . . .
H11 H -0.2617 1.4476 0.7845 0.032 Uiso 1 1 calc R . .
C12 C 0.4892(4) 0.78049(19) 0.71527(14) 0.0221(4) Uani 1 1 d . . .
H12A H 0.4187 0.7242 0.7600 0.027 Uiso 1 1 calc R . .
H12B H 0.6172 0.7315 0.6741 0.027 Uiso 1 1 calc R . .
C13 C 0.6364(4) 0.89825(18) 0.78048(14) 0.0208(3) Uani 1 1 d . . .
H13A H 0.7087 0.9553 0.7367 0.025 Uiso 1 1 calc R . .
H13B H 0.5116 0.9470 0.8234 0.025 Uiso 1 1 calc R . .
C14 C 0.8597(4) 0.85897(19) 0.84636(14) 0.0215(4) Uani 1 1 d . . .
C15 C 0.4336(4) 0.7471(2) 0.00909(15) 0.0273(4) Uani 1 1 d . . .
C16 C 0.6546(5) 0.7054(3) 0.07368(18) 0.0347(5) Uani 1 1 d . . .
H16A H 0.8041 0.7703 0.0840 0.052 Uiso 1 1 calc R . .
H16B H 0.7124 0.6226 0.0401 0.052 Uiso 1 1 calc R . .
H16C H 0.5921 0.6960 0.1392 0.052 Uiso 1 1 calc R . .
O1 O 0.8831(3) 0.74730(14) 0.85701(11) 0.0260(3) Uani 1 1 d . . .
O2 O 1.0265(3) 0.95564(14) 0.89125(11) 0.0254(3) Uani 1 1 d . . .
H2A H 1.1417 0.9283 0.9291 0.038 Uiso 1 1 calc R . .
O3 O 0.4061(3) 0.85949(16) 0.00284(13) 0.0323(4) Uani 1 1 d . . .
O4 O 0.2707(3) 0.65131(17) -0.03928(14) 0.0356(4) Uani 1 1 d . . .
H4A H 0.1443 0.6809 -0.0703 0.053 Uiso 1 1 calc R . .
S1 S 0.21600(9) 0.81635(5) 0.63114(3) 0.02082(14) Uani 1 1 d . . .
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 C11 120.95(19) . 2_676
C2 C1 H1 119.5 . .
C11 C1 H1 119.5 2_676 .
C1 C2 C3 120.4(2) . .
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 . .
C4 C3 C2 121.99(19) . .
C4 C3 C9 119.07(18) . 2_676
C2 C3 C9 118.94(18) . 2_676
C3 C4 C5 122.30(18) . .
C3 C4 H4 118.8 . .
C5 C4 H4 118.8 . .
C6 C5 C4 121.98(17) . .
C6 C5 C7 119.66(16) . 2_676
C4 C5 C7 118.36(16) . 2_676
C7 C6 C5 120.93(17) . .
C7 C6 S1 118.89(13) . .
C5 C6 S1 120.14(14) . .
C8 C7 C6 122.60(17) . .
C8 C7 C5 118.00(17) . 2_676
C6 C7 C5 119.40(16) . 2_676
C9 C8 C7 122.73(18) . .
C9 C8 H8 118.6 . .
C7 C8 H8 118.6 . .
C8 C9 C3 119.44(17) . 2_676
C8 C9 C10 121.99(18) . .
C3 C9 C10 118.56(18) 2_676 .
C11 C10 C9 120.44(19) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C1 120.67(19) . 2_676
C10 C11 H11 119.7 . .
C1 C11 H11 119.7 2_676 .
C13 C12 S1 114.47(13) . .
C13 C12 H12A 108.6 . .
S1 C12 H12A 108.6 . .
C13 C12 H12B 108.6 . .
S1 C12 H12B 108.6 . .
H12A C12 H12B 107.6 . .
C14 C13 C12 110.51(16) . .
C14 C13 H13A 109.5 . .
C12 C13 H13A 109.5 . .
C14 C13 H13B 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 108.1 . .
O1 C14 O2 123.42(18) . .
O1 C14 C13 122.62(18) . .
O2 C14 C13 113.96(17) . .
O3 C15 O4 123.4(2) . .
O3 C15 C16 122.9(2) . .
O4 C15 C16 113.7(2) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C14 O2 H2A 109.5 . .
C15 O4 H4A 109.5 . .
C6 S1 C12 102.16(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.362(3) .
C1 C11 1.422(3) 2_676
C1 H1 0.9500 .
C2 C3 1.427(3) .
C2 H2 0.9500 .
C3 C4 1.388(3) .
C3 C9 1.436(3) 2_676
C4 C5 1.416(3) .
C4 H4 0.9500 .
C5 C6 1.414(2) .
C5 C7 1.454(3) 2_676
C6 C7 1.413(3) .
C6 S1 1.7785(19) .
C7 C8 1.411(2) .
C7 C5 1.454(3) 2_676
C8 C9 1.380(3) .
C8 H8 0.9500 .
C9 C3 1.436(3) 2_676
C9 C10 1.440(3) .
C10 C11 1.358(3) .
C10 H10 0.9500 .
C11 C1 1.422(3) 2_676
C11 H11 0.9500 .
C12 C13 1.517(3) .
C12 S1 1.817(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.502(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 O1 1.222(2) .
C14 O2 1.320(2) .
C15 O3 1.217(3) .
C15 O4 1.317(3) .
C15 C16 1.495(3) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
O2 H2A 0.8400 .
O4 H4A 0.8400 .
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
C11 C1 C2 C3 -0.1(3) 2_676 . . .
C1 C2 C3 C4 180.0(2) . . . .
C1 C2 C3 C9 0.4(3) . . . 2_676
C2 C3 C4 C5 178.92(18) . . . .
C9 C3 C4 C5 -1.5(3) 2_676 . . .
C3 C4 C5 C6 -177.99(18) . . . .
C3 C4 C5 C7 3.0(3) . . . 2_676
C4 C5 C6 C7 -178.29(17) . . . .
C7 C5 C6 C7 0.7(3) 2_676 . . .
C4 C5 C6 S1 -0.4(3) . . . .
C7 C5 C6 S1 178.57(13) 2_676 . . .
C5 C6 C7 C8 179.46(17) . . . .
S1 C6 C7 C8 1.6(3) . . . .
C5 C6 C7 C5 -0.7(3) . . . 2_676
S1 C6 C7 C5 -178.59(13) . . . 2_676
C6 C7 C8 C9 -178.72(18) . . . .
C5 C7 C8 C9 1.5(3) 2_676 . . .
C7 C8 C9 C3 -3.0(3) . . . 2_676
C7 C8 C9 C10 178.04(18) . . . .
C8 C9 C10 C11 177.84(19) . . . .
C3 C9 C10 C11 -1.2(3) 2_676 . . .
C9 C10 C11 C1 0.9(3) . . . 2_676
S1 C12 C13 C14 -179.39(13) . . . .
C12 C13 C14 O1 -11.9(2) . . . .
C12 C13 C14 O2 168.12(15) . . . .
C7 C6 S1 C12 -111.35(15) . . . .
C5 C6 S1 C12 70.76(16) . . . .
C13 C12 S1 C6 57.64(15) . . . .
