#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:52:45 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228751 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/90/1549096.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_1549096
loop_
_publ_author_name
'van der Lee, Arie'
'Roche, Gilles H.'
'Wantz, Guillaume'
'Moreau, Joël J E'
'Dautel, Olivier J.'
'Filhol, Jean-Sébastien'
_publ_section_title
;
 Experimental and theoretical evidence of a supercritical-like transition
 in an organic semiconductor presenting colossal uniaxial negative thermal
 expansion.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              3948
_journal_page_last               3956
_journal_paper_doi               10.1039/c8sc00159f
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C26 H32 O2 S2'
_chemical_formula_sum            'C26 H32 O2 S2'
_chemical_formula_weight         440.66
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_update_record
;
2017-12-12 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.255(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0891(6)
_cell_length_b                   5.7282(4)
_cell_length_c                   49.849(4)
_cell_measurement_reflns_used    2290
_cell_measurement_temperature    215
_cell_measurement_theta_max      27.5340
_cell_measurement_theta_min      3.5980
_cell_volume                     2303.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      215
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0143
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  82.00   1.00   15.00    --   13.31  57.00  90.00   87
  2  ω     -3.00  27.00   1.00   15.00    --  -14.02-100.00  90.00   30
  3  ω    -59.00  46.00   1.00   15.00    --   13.31 -19.00 -90.00  105
  4  ω    -42.00  52.00   1.00   15.00    --  -14.02  77.00-150.00   94
  5  ω    -50.00 -24.00   1.00   15.00    --  -14.02 108.00 -92.00   26
;
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0407023000
_diffrn_orient_matrix_UB_12      -0.0424737000
_diffrn_orient_matrix_UB_13      -0.0111331000
_diffrn_orient_matrix_UB_21      -0.0732454000
_diffrn_orient_matrix_UB_22      0.0182101000
_diffrn_orient_matrix_UB_23      -0.0084808000
_diffrn_orient_matrix_UB_31      0.0266724000
_diffrn_orient_matrix_UB_32      0.1148859000
_diffrn_orient_matrix_UB_33      -0.0027701000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            7662
_diffrn_reflns_theta_full        25.226
_diffrn_reflns_theta_max         27.948
_diffrn_reflns_theta_min         2.458
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8551
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.0039958
_refine_ls_shift/su_mean         0.0001075
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.159E+04 0.261E+04 0.159E+04 659. 140. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0773
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0736
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              64
_reflns_limit_l_min              0
_reflns_number_gt                2106
_reflns_number_total             2362
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0357
_oxford_refine_ls_scale          3.96(4)
_oxford_reflns_number_all        2362
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c8sc00159f2.cif
_cod_data_source_block           215K
_cod_depositor_comments
'Adding full bibliography for 1549094--1549104.cif.'
_cod_original_cell_volume        2303.46(19)
_cod_original_sg_symbol_H-M      'I 1 2/a 1 '
_cod_database_code               1549096
_cell_oxdiff_length_a            8.0888(5)
_cell_oxdiff_length_b            5.7279(3)
_cell_oxdiff_length_c            49.857(3)
_cell_oxdiff_angle_alpha         90.005(5)
_cell_oxdiff_angle_beta          94.304(5)
_cell_oxdiff_angle_gamma         90.009(5)
_cell_oxdiff_volume              2303.5(2)
_oxdiff_exptl_absorpt_empirical_full_min 0.950
_oxdiff_exptl_absorpt_empirical_full_max 1.047
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_montpellier_reflns_maxres       0.76
_montpellier_reflns_completeness_maxres 85.69
_montpellier_reflns_redundancy_maxres 3.09
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z+1/2
-x+1/2,-y+1/2,-z+1/2
-x+1/2,y,-z
x+1/2,-y,z
-x+1,y+1/2,-z+1/2
x+1,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
S1 S 0.84771(4) 0.54097(6) 0.731488(6) 0.0341 1.0000 Uani .
C2 C 0.75007(16) 0.3708(2) 0.70601(2) 0.0299 1.0000 Uani .
C3 C 0.68010(15) 0.1661(2) 0.71575(2) 0.0283 1.0000 Uani .
C4 C 0.70792(15) 0.1569(2) 0.74446(2) 0.0274 1.0000 Uani .
C5 C 0.59538(17) 0.0159(3) 0.69754(3) 0.0350 1.0000 Uani .
C6 C 0.58138(19) 0.0740(3) 0.67055(3) 0.0413 1.0000 Uani .
C7 C 0.64979(18) 0.2782(3) 0.66087(3) 0.0382 1.0000 Uani .
C8 C 0.73606(18) 0.4273(3) 0.67869(3) 0.0355 1.0000 Uani .
C9 C 0.6346(2) 0.3355(3) 0.63112(3) 0.0477 1.0000 Uani .
C10 C 0.7667(2) 0.2184(3) 0.61572(3) 0.0464 1.0000 Uani .
C11 C 0.7694(2) 0.3022(4) 0.58671(3) 0.0527 1.0000 Uani .
C12 C 0.9079(2) 0.1944(4) 0.57210(3) 0.0572 1.0000 Uani .
C13 C 0.9244(3) 0.2971(4) 0.54419(3) 0.0635 1.0000 Uani .
C14 C 1.0705(3) 0.1990(5) 0.53117(4) 0.0727 1.0000 Uani .
O15 O 1.0888(2) 0.3038(4) 0.50559(3) 0.0884 1.0000 Uani .
H51 H 0.5484 -0.1212 0.7034 0.0408 1.0000 Uiso R
H61 H 0.5221 -0.0268 0.6583 0.0502 1.0000 Uiso R
H81 H 0.7832 0.5662 0.6727 0.0412 1.0000 Uiso R
H91 H 0.6438 0.5036 0.6294 0.0564 1.0000 Uiso R
H92 H 0.5247 0.2868 0.6236 0.0569 1.0000 Uiso R
H101 H 0.8760 0.2490 0.6252 0.0541 1.0000 Uiso R
H102 H 0.7484 0.0515 0.6161 0.0546 1.0000 Uiso R
H111 H 0.7837 0.4700 0.5871 0.0625 1.0000 Uiso R
H112 H 0.6625 0.2657 0.5769 0.0619 1.0000 Uiso R
H121 H 1.0124 0.2200 0.5829 0.0669 1.0000 Uiso R
H122 H 0.8899 0.0266 0.5706 0.0674 1.0000 Uiso R
H131 H 0.9383 0.4630 0.5461 0.0744 1.0000 Uiso R
H132 H 0.8221 0.2695 0.5327 0.0743 1.0000 Uiso R
H141 H 1.1717 0.2277 0.5426 0.0866 1.0000 Uiso R
H142 H 1.0563 0.0336 0.5281 0.0861 1.0000 Uiso R
H151 H 1.0398 0.4232 0.5046 0.1141 0.5000 Uiso .
H152 H 1.1853 0.3039 0.5033 0.1140 0.5000 Uiso .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_i/ui
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.80 4.9 91.89 0.017 99.2 99.24
1 1.79 1.39 4.4 62.33 0.021 100.0 99.62
2 1.39 1.22 4.0 44.31 0.026 100.0 99.74
3 1.21 1.10 3.3 31.05 0.028 100.0 99.81
4 1.10 1.02 3.1 22.10 0.033 100.0 99.85
5 1.02 0.95 2.7 16.37 0.040 100.0 99.87
6 0.95 0.90 2.6 14.09 0.051 100.0 99.89
7 0.90 0.86 2.3 11.10 0.056 100.0 99.90
8 0.86 0.83 2.1 10.02 0.058 93.9 99.19
9 0.83 0.76 1.4 7.65 0.069 38.9 85.69
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 4_656 S1 C2 . 90.65(6) yes
S1 . C2 C3 . 112.80(9) yes
S1 . C2 C8 . 125.50(11) yes
C3 . C2 C8 . 121.69(13) yes
C2 . C3 C4 . 109.79(12) yes
C2 . C3 C5 . 118.81(12) yes
C4 . C3 C5 . 131.37(13) yes
C3 . C4 S1 4_656 133.25(10) yes
C3 . C4 C4 4_656 114.42(14) yes
S1 4_656 C4 C4 4_656 112.31(12) yes
C3 . C5 C6 . 119.08(14) yes
C3 . C5 H51 . 120.6 no
C6 . C5 H51 . 120.3 no
C5 . C6 C7 . 122.16(14) yes
C5 . C6 H61 . 118.8 no
C7 . C6 H61 . 119.0 no
C6 . C7 C8 . 119.33(13) yes
C6 . C7 C9 . 120.98(14) yes
C8 . C7 C9 . 119.68(15) yes
C2 . C8 C7 . 118.93(14) yes
C2 . C8 H81 . 120.1 no
C7 . C8 H81 . 120.9 no
C7 . C9 C10 . 113.00(13) yes
C7 . C9 H91 . 107.5 no
C10 . C9 H91 . 109.4 no
C7 . C9 H92 . 108.5 no
C10 . C9 H92 . 109.5 no
H91 . C9 H92 . 108.8 no
C9 . C10 C11 . 113.62(14) yes
C9 . C10 H101 . 108.6 no
C11 . C10 H101 . 108.8 no
C9 . C10 H102 . 108.2 no
C11 . C10 H102 . 110.0 no
H101 . C10 H102 . 107.4 no
C10 . C11 C12 . 113.02(15) yes
C10 . C11 H111 . 107.8 no
C12 . C11 H111 . 108.8 no
C10 . C11 H112 . 109.4 no
C12 . C11 H112 . 109.1 no
H111 . C11 H112 . 108.6 no
C11 . C12 C13 . 113.54(17) yes
C11 . C12 H121 . 108.2 no
C13 . C12 H121 . 108.4 no
C11 . C12 H122 . 109.2 no
C13 . C12 H122 . 109.3 no
H121 . C12 H122 . 108.0 no
C12 . C13 C14 . 112.03(18) yes
C12 . C13 H131 . 108.1 no
C14 . C13 H131 . 108.8 no
C12 . C13 H132 . 110.0 no
C14 . C13 H132 . 110.2 no
H131 . C13 H132 . 107.6 no
C13 . C14 O15 . 111.51(19) yes
C13 . C14 H141 . 109.8 no
O15 . C14 H141 . 108.1 no
C13 . C14 H142 . 110.4 no
O15 . C14 H142 . 106.8 no
H141 . C14 H142 . 110.1 no
C14 . O15 H151 . 109.5 no
C14 . O15 H152 . 107.1 no
H151 . O15 H152 . 118.9 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C4 4_656 1.7335(13) yes
S1 C2 . 1.7432(14) yes
C2 C3 . 1.4040(19) yes
C2 C8 . 1.3961(18) yes
C3 C4 . 1.4333(17) yes
C3 C5 . 1.3933(19) yes
C4 C4 4_656 1.360(3) yes
C5 C6 . 1.382(2) yes
C5 H51 . 0.929 no
C6 C7 . 1.395(2) yes
C6 H61 . 0.944 no
C7 C8 . 1.383(2) yes
C7 C9 . 1.5153(19) yes
C8 H81 . 0.941 no
C9 C10 . 1.517(2) yes
C9 H91 . 0.970 no
C9 H92 . 0.980 no
C10 C11 . 1.5251(19) yes
C10 H101 . 0.987 no
C10 H102 . 0.968 no
C11 C12 . 1.513(2) yes
C11 H111 . 0.968 no
C11 H112 . 0.984 no
C12 C13 . 1.526(2) yes
C12 H121 . 0.979 no
C12 H122 . 0.974 no
C13 C14 . 1.499(3) yes
C13 H131 . 0.961 no
C13 H132 . 0.982 no
C14 O15 . 1.427(2) yes
C14 H141 . 0.976 no
C14 H142 . 0.965 no
O15 H151 . 0.790 no
O15 H152 . 0.796 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O15 H151 O15 2_766 167.85(7) 0.790 1.926 2.703(2) yes
O15 H152 O15 5_756 174.65(6) 0.796 1.913 2.707(2) yes
