#------------------------------------------------------------------------------
#$Date: 2016-03-05 13:03:38 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177940 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/04/1540454.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_1540454
loop_
_publ_author_name
'Nell, Kara M.'
'Fontenot, Sean A.'
'Carter, Timothy G.'
'Warner, Marvin G.'
'Warner, Cynthia L.'
'Addleman, R. Shane'
'Johnson, Darren W.'
_publ_section_title
;
 Non-covalent functionalization of high-surface area nanomaterials: a new
 class of sorbent materials
;
_journal_issue                   1
_journal_name_full               'Environ. Sci.: Nano'
_journal_page_first              138
_journal_paper_doi               10.1039/C5EN00170F
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C20 H14 S2'
_chemical_formula_weight         318.43
_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           SHELXLTL
_audit_update_record
;
2015-06-24 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                92.804(3)
_cell_angle_beta                 110.458(3)
_cell_angle_gamma                116.890(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9174(18)
_cell_length_b                   9.1478(19)
_cell_length_c                   11.846(2)
_cell_measurement_reflns_used    2941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.66
_cell_volume                     782.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8776
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0423
_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)+(0.0664P)²+0.3134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                2854
_reflns_number_total             3390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5en00170f2.cif
_cod_data_source_block           sean12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1540454.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1540454
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
S1 S 0.44332(7) 0.26782(6) 0.39032(4) 0.02829(15) Uani 1 1 d
S2 S 0.09770(8) -0.04366(7) 0.35630(5) 0.04203(18) Uani 1 1 d
C1 C 0.2468(3) 0.0749(2) 0.30350(18) 0.0274(4) Uani 1 1 d
C2 C 0.2384(2) 0.0368(2) 0.17884(17) 0.0246(4) Uani 1 1 d
C3 C 0.3797(2) 0.1629(2) 0.15646(17) 0.0247(4) Uani 1 1 d
C4 C 0.5148(2) 0.3225(2) 0.26109(16) 0.0236(4) Uani 1 1 d
C5 C 0.3901(3) 0.1382(3) 0.04383(19) 0.0311(4) Uani 1 1 d
C6 C 0.2569(3) -0.0117(3) -0.0472(2) 0.0347(5) Uani 1 1 d
C7 C 0.1141(3) -0.1373(3) -0.0248(2) 0.0328(5) Uani 1 1 d
C8 C 0.1047(3) -0.1142(2) 0.08784(19) 0.0296(4) Uani 1 1 d
C9 C 0.7139(2) 0.3587(2) 0.29601(16) 0.0242(4) Uani 1 1 d
C10 C 0.7743(3) 0.2579(3) 0.3596(2) 0.0333(4) Uani 1 1 d
C11 C 0.9481(3) 0.2813(3) 0.3831(2) 0.0387(5) Uani 1 1 d
C12 C 1.0646(3) 0.4065(3) 0.3444(2) 0.0391(5) Uani 1 1 d
C13 C 1.0065(3) 0.5075(3) 0.2817(2) 0.0384(5) Uani 1 1 d
C14 C 0.8312(3) 0.4833(3) 0.2568(2) 0.0317(4) Uani 1 1 d
C15 C 0.4915(2) 0.4751(2) 0.23473(17) 0.0240(4) Uani 1 1 d
C16 C 0.6027(3) 0.6276(3) 0.32553(19) 0.0301(4) Uani 1 1 d
C17 C 0.5805(3) 0.7661(3) 0.3083(2) 0.0339(5) Uani 1 1 d
C18 C 0.4443(3) 0.7546(3) 0.1995(2) 0.0328(4) Uani 1 1 d
C19 C 0.3330(3) 0.6044(3) 0.1087(2) 0.0336(5) Uani 1 1 d
C20 C 0.3577(3) 0.4659(3) 0.12554(18) 0.0287(4) Uani 1 1 d
H5 H 0.478(3) 0.219(3) 0.026(2) 0.031(6) Uiso 1 1 d
H6 H 0.262(3) -0.027(3) -0.127(2) 0.041(6) Uiso 1 1 d
H7 H 0.028(3) -0.237(3) -0.085(2) 0.033(6) Uiso 1 1 d
H8 H 0.015(3) -0.197(3) 0.110(2) 0.033(6) Uiso 1 1 d
H10 H 0.697(3) 0.175(3) 0.391(2) 0.038(6) Uiso 1 1 d
H11 H 0.983(3) 0.208(3) 0.429(2) 0.044(7) Uiso 1 1 d
H12 H 1.184(3) 0.431(3) 0.353(2) 0.029(5) Uiso 1 1 d
H13 H 1.088(4) 0.598(3) 0.255(2) 0.047(7) Uiso 1 1 d
H14 H 0.797(3) 0.551(3) 0.218(2) 0.032(6) Uiso 1 1 d
H16 H 0.690(3) 0.636(3) 0.398(2) 0.039(6) Uiso 1 1 d
H17 H 0.654(3) 0.869(3) 0.371(2) 0.044(7) Uiso 1 1 d
H18 H 0.430(3) 0.850(3) 0.187(2) 0.043(6) Uiso 1 1 d
H19 H 0.243(3) 0.597(3) 0.033(2) 0.042(7) Uiso 1 1 d
H20 H 0.288(3) 0.364(3) 0.061(2) 0.032(6) Uiso 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'
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
C1 S1 C4 95.98(9)
C2 C1 S2 126.51(15)
C2 C1 S1 109.55(14)
S2 C1 S1 123.94(12)
C3 C2 C8 120.67(18)
C3 C2 C1 114.74(16)
C8 C2 C1 124.57(18)
C5 C3 C2 119.84(17)
C5 C3 C4 124.13(17)
C2 C3 C4 116.03(16)
C3 C4 C15 113.70(15)
C3 C4 C9 109.72(14)
C15 C4 C9 113.08(14)
C3 C4 S1 103.17(12)
C15 C4 S1 105.41(12)
C9 C4 S1 111.24(12)
C3 C5 C6 119.67(19)
C3 C5 H5 121.8(14)
C6 C5 H5 118.4(14)
C5 C6 C7 120.29(19)
C5 C6 H6 119.6(15)
C7 C6 H6 120.1(15)
C8 C7 C6 120.24(18)
C8 C7 H7 120.3(14)
C6 C7 H7 119.4(14)
C7 C8 C2 119.28(19)
C7 C8 H8 123.7(14)
C2 C8 H8 117.0(14)
C14 C9 C10 118.74(18)
C14 C9 C4 120.75(17)
C10 C9 C4 120.33(17)
C11 C10 C9 120.7(2)
C11 C10 H10 119.6(14)
C9 C10 H10 119.6(14)
C12 C11 C10 120.2(2)
C12 C11 H11 123.0(15)
C10 C11 H11 116.8(15)
C13 C12 C11 119.6(2)
C13 C12 H12 113.5(13)
C11 C12 H12 126.9(13)
C12 C13 C14 120.4(2)
C12 C13 H13 120.5(15)
C14 C13 H13 119.1(15)
C9 C14 C13 120.4(2)
C9 C14 H14 120.4(15)
C13 C14 H14 119.2(15)
C20 C15 C16 118.21(18)
C20 C15 C4 122.49(16)
C16 C15 C4 119.24(16)
C17 C16 C15 121.26(19)
C17 C16 H16 119.4(15)
C15 C16 H16 119.4(15)
C16 C17 C18 120.04(19)
C16 C17 H17 121.4(15)
C18 C17 H17 118.6(15)
C19 C18 C17 119.39(19)
C19 C18 H18 120.3(15)
C17 C18 H18 120.3(15)
C18 C19 C20 120.42(19)
C18 C19 H19 120.0(15)
C20 C19 H19 119.5(15)
C15 C20 C19 120.66(18)
C15 C20 H20 118.1(13)
C19 C20 H20 121.2(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.734(2)
S1 C4 1.8625(19)
S2 C1 1.636(2)
C1 C2 1.468(3)
C2 C3 1.392(3)
C2 C8 1.400(3)
C3 C5 1.384(3)
C3 C4 1.519(2)
C4 C15 1.533(3)
C4 C9 1.540(2)
C5 C6 1.393(3)
C5 H5 0.90(2)
C6 C7 1.398(3)
C6 H6 0.96(3)
C7 C8 1.378(3)
C7 H7 0.92(2)
C8 H8 0.95(2)
C9 C14 1.386(3)
C9 C10 1.394(3)
C10 C11 1.385(3)
C10 H10 0.96(2)
C11 C12 1.381(3)
C11 H11 0.98(3)
C12 C13 1.381(3)
C12 H12 0.95(2)
C13 C14 1.392(3)
C13 H13 0.98(3)
C14 H14 0.89(2)
C15 C20 1.386(3)
C15 C16 1.393(3)
C16 C17 1.382(3)
C16 H16 0.91(2)
C17 C18 1.387(3)
C17 H17 0.95(3)
C18 C19 1.380(3)
C18 H18 0.94(3)
C19 C20 1.394(3)
C19 H19 0.95(3)
C20 H20 0.95(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
C4 S1 C1 C2 5.80(14)
C4 S1 C1 S2 -174.68(13)
S2 C1 C2 C3 177.59(14)
S1 C1 C2 C3 -2.9(2)
S2 C1 C2 C8 -4.1(3)
S1 C1 C2 C8 175.37(15)
C8 C2 C3 C5 -0.9(3)
C1 C2 C3 C5 177.47(17)
C8 C2 C3 C4 178.98(16)
C1 C2 C3 C4 -2.7(2)
C5 C3 C4 C15 72.6(2)
C2 C3 C4 C15 -107.26(18)
C5 C3 C4 C9 -55.1(2)
C2 C3 C4 C9 124.99(17)
C5 C3 C4 S1 -173.77(16)
C2 C3 C4 S1 6.37(19)
C1 S1 C4 C3 -6.76(13)
C1 S1 C4 C15 112.76(12)
C1 S1 C4 C9 -124.33(13)
C2 C3 C5 C6 1.1(3)
C4 C3 C5 C6 -178.73(18)
C3 C5 C6 C7 -0.5(3)
C5 C6 C7 C8 -0.4(3)
C6 C7 C8 C2 0.7(3)
C3 C2 C8 C7 0.0(3)
C1 C2 C8 C7 -178.19(18)
C3 C4 C9 C14 102.9(2)
C15 C4 C9 C14 -25.2(2)
S1 C4 C9 C14 -143.58(16)
C3 C4 C9 C10 -72.2(2)
C15 C4 C9 C10 159.72(17)
S1 C4 C9 C10 41.3(2)
C14 C9 C10 C11 -0.1(3)
C4 C9 C10 C11 175.07(18)
C9 C10 C11 C12 0.5(3)
C10 C11 C12 C13 -0.4(3)
C11 C12 C13 C14 -0.2(3)
C10 C9 C14 C13 -0.5(3)
C4 C9 C14 C13 -175.66(18)
C12 C13 C14 C9 0.7(3)
C3 C4 C15 C20 0.5(2)
C9 C4 C15 C20 126.50(18)
S1 C4 C15 C20 -111.77(17)
C3 C4 C15 C16 177.63(17)
C9 C4 C15 C16 -56.4(2)
S1 C4 C15 C16 65.35(18)
C20 C15 C16 C17 0.4(3)
C4 C15 C16 C17 -176.83(18)
C15 C16 C17 C18 0.6(3)
C16 C17 C18 C19 -0.5(3)
C17 C18 C19 C20 -0.5(3)
C16 C15 C20 C19 -1.5(3)
C4 C15 C20 C19 175.69(17)
C18 C19 C20 C15 1.5(3)
