#------------------------------------------------------------------------------
#$Date: 2019-11-17 07:52:45 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228751 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/91/1549101.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_1549101
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                 92.829(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4460(3)
_cell_length_b                   5.58942(19)
_cell_length_c                   50.2534(15)
_cell_measurement_reflns_used    7687
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.8380
_cell_measurement_theta_min      2.4300
_cell_volume                     2369.48(14)
_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      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0143
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_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   17.23    --   13.47  57.00-180.00   87
  2  ω    -58.00  85.00   1.00   17.23    --   13.47   0.00 150.00  143
  3  ω    -55.00  32.00   1.00   17.23    --   13.47 -57.00 -60.00   87
  4  ω    -78.00 -27.00   1.00   17.23    --  -14.10 139.00-162.16   51
  5  ω    -78.00 -28.00   1.00   17.23    --  -14.10 140.00 -39.64   50
  6  ω    -24.00  27.00   1.00   17.23    --  -14.10-100.00  90.00   51
  7  ω    -24.00  54.00   1.00   17.23    --   13.47-100.00 150.00   78
  8  ω    -55.00  32.00   1.00   17.23    --   13.47 -57.00  30.00   87
  9  ω    -24.00  27.00   1.00   17.23    --  -14.10-100.00 -60.00   51
 10  ω    -76.00 -26.00   1.00   17.23    --  -14.10 137.00  40.52   50
 11  ω    -86.00  24.00   1.00   17.23    --  -14.10 -19.00-150.00  110
 12  ω    -79.00 -54.00   1.00   17.23    --  -14.10 141.00 115.90   25
 13  ω    -24.00  27.00   1.00   17.23    --  -14.10-100.00   0.00   51
;
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0724129000
_diffrn_orient_matrix_UB_12      -0.0460898000
_diffrn_orient_matrix_UB_13      0.0044178000
_diffrn_orient_matrix_UB_21      0.0363319000
_diffrn_orient_matrix_UB_22      -0.0193741000
_diffrn_orient_matrix_UB_23      0.0128467000
_diffrn_orient_matrix_UB_31      -0.0225761000
_diffrn_orient_matrix_UB_32      0.1166522000
_diffrn_orient_matrix_UB_33      0.0038760000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       65
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            20985
_diffrn_reflns_theta_full        25.226
_diffrn_reflns_theta_max         27.910
_diffrn_reflns_theta_min         1.623
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97486
_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    1.235
_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         0.22
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.7832
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.0044045
_refine_ls_shift/su_mean         0.0001175
_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: 
 0.187E+04 0.311E+04 0.186E+04 733. 146.
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0972
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0915
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              65
_reflns_limit_l_min              0
_reflns_number_gt                2345
_reflns_number_total             2631
_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   0.0394
_oxford_refine_ls_scale          4.02(5)
_oxford_reflns_number_all        2631
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c8sc00159f2.cif
_cod_data_source_block           295K
_cod_depositor_comments
'Adding full bibliography for 1549094--1549104.cif.'
_cod_original_cell_volume        2369.48(7)
_cod_original_sg_symbol_H-M      'I 1 2/a 1 '
_cod_database_code               1549101
_cell_oxdiff_length_a            8.4442(3)
_cell_oxdiff_length_b            5.58879(16)
_cell_oxdiff_length_c            50.2708(11)
_cell_oxdiff_angle_alpha         89.988(2)
_cell_oxdiff_angle_beta          92.863(2)
_cell_oxdiff_angle_gamma         90.001(3)
_cell_oxdiff_volume              2369.48(13)
_oxdiff_exptl_absorpt_empirical_full_min 0.946
_oxdiff_exptl_absorpt_empirical_full_max 1.057
_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 91.93
_montpellier_reflns_redundancy_maxres 7.62
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 0.85632(5) 0.54038(7) 0.731557(7) 0.0473 1.0000 Uani .
C2 C 0.76037(16) 0.3718(3) 0.70635(3) 0.0398 1.0000 Uani .
C3 C 0.68463(15) 0.1669(2) 0.71609(2) 0.0373 1.0000 Uani .
C4 C 0.70707(15) 0.1572(2) 0.74458(2) 0.0366 1.0000 Uani .
C5 C 0.60121(19) 0.0180(3) 0.69809(3) 0.0483 1.0000 Uani .
C6 C 0.5930(2) 0.0762(3) 0.67141(3) 0.0555 1.0000 Uani .
C7 C 0.66686(19) 0.2804(3) 0.66166(3) 0.0510 1.0000 Uani .
C8 C 0.75193(18) 0.4283(3) 0.67926(3) 0.0479 1.0000 Uani .
C9 C 0.6572(2) 0.3396(4) 0.63211(3) 0.0639 1.0000 Uani .
C10 C 0.7853(2) 0.2171(4) 0.61684(3) 0.0624 1.0000 Uani .
C11 C 0.7906(2) 0.3038(4) 0.58815(3) 0.0699 1.0000 Uani .
C12 C 0.9228(3) 0.1910(5) 0.57321(3) 0.0777 1.0000 Uani .
C13 C 0.9402(3) 0.3029(6) 0.54565(4) 0.0880 1.0000 Uani .
C14 C 1.0788(3) 0.2024(6) 0.53182(4) 0.1020 1.0000 Uani .
O15 O 1.0980(2) 0.3163(5) 0.50711(3) 0.1305 1.0000 Uani .
H51 H 0.5497 -0.1207 0.7043 0.0571 1.0000 Uiso R
H61 H 0.5319 -0.0229 0.6593 0.0674 1.0000 Uiso R
H81 H 0.8036 0.5641 0.6732 0.0564 1.0000 Uiso R
H91 H 0.6678 0.5141 0.6307 0.0760 1.0000 Uiso R
H92 H 0.5493 0.2909 0.6250 0.0763 1.0000 Uiso R
H101 H 0.8898 0.2489 0.6261 0.0755 1.0000 Uiso R
H102 H 0.7667 0.0440 0.6171 0.0755 1.0000 Uiso R
H111 H 0.8030 0.4766 0.5875 0.0849 1.0000 Uiso R
H112 H 0.6901 0.2647 0.5789 0.0828 1.0000 Uiso R
H121 H 1.0245 0.2171 0.5836 0.0920 1.0000 Uiso R
H122 H 0.9038 0.0189 0.5716 0.0926 1.0000 Uiso R
H131 H 0.9543 0.4771 0.5479 0.1055 1.0000 Uiso R
H132 H 0.8428 0.2781 0.5349 0.1045 1.0000 Uiso R
H141 H 1.1770 0.2247 0.5434 0.1234 1.0000 Uiso R
H142 H 1.0609 0.0320 0.5280 0.1242 1.0000 Uiso R
H151 H 1.0411 0.4260 0.5048 0.1640 0.5000 Uiso R
H152 H 1.1865 0.3067 0.5035 0.1640 0.5000 Uiso R
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'
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 1.74 13.3 156.01 0.026 99.7 99.65
1 1.73 1.37 11.4 94.03 0.026 100.0 99.83
2 1.37 1.19 10.6 75.07 0.029 100.0 99.88
3 1.19 1.07 8.7 49.88 0.030 100.0 99.91
4 1.07 0.99 7.6 30.98 0.042 100.0 99.93
5 0.99 0.93 7.1 23.52 0.058 100.0 99.94
6 0.93 0.88 6.7 18.60 0.063 100.0 99.95
7 0.88 0.84 6.0 14.93 0.078 100.0 99.96
8 0.84 0.81 3.3 10.08 0.089 95.4 99.42
9 0.81 0.76 1.7 6.90 0.092 55.0 91.93
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 . 90.56(6) yes
S1 . C2 C3 . 112.88(9) yes
S1 . C2 C8 . 125.80(12) yes
C3 . C2 C8 . 121.30(13) yes
C2 . C3 C4 . 109.66(11) yes
C2 . C3 C5 . 118.85(12) yes
C4 . C3 C5 . 131.46(13) yes
C3 . C4 S1 4_656 133.10(10) yes
C3 . C4 C4 4_656 114.26(14) yes
S1 4_656 C4 C4 4_656 112.62(13) yes
C3 . C5 C6 . 119.34(14) yes
C3 . C5 H51 . 119.9 no
C6 . C5 H51 . 120.7 no
C5 . C6 C7 . 122.05(14) yes
C5 . C6 H61 . 119.0 no
C7 . C6 H61 . 118.9 no
C6 . C7 C8 . 119.25(13) yes
C6 . C7 C9 . 121.06(15) yes
C8 . C7 C9 . 119.68(16) yes
C2 . C8 C7 . 119.19(15) yes
C2 . C8 H81 . 120.0 no
C7 . C8 H81 . 120.8 no
C7 . C9 C10 . 112.93(14) yes
C7 . C9 H91 . 106.7 no
C10 . C9 H91 . 109.9 no
C7 . C9 H92 . 107.1 no
C10 . C9 H92 . 110.8 no
H91 . C9 H92 . 109.2 no
C9 . C10 C11 . 112.90(16) yes
C9 . C10 H101 . 108.7 no
C11 . C10 H101 . 108.6 no
C9 . C10 H102 . 108.5 no
C11 . C10 H102 . 109.9 no
H101 . C10 H102 . 108.0 no
C10 . C11 C12 . 113.18(17) yes
C10 . C11 H111 . 111.0 no
C12 . C11 H111 . 108.2 no
C10 . C11 H112 . 108.5 no
C12 . C11 H112 . 108.4 no
H111 . C11 H112 . 107.4 no
C11 . C12 C13 . 112.58(19) yes
C11 . C12 H121 . 108.6 no
C13 . C12 H121 . 107.1 no
C11 . C12 H122 . 109.2 no
C13 . C12 H122 . 110.5 no
H121 . C12 H122 . 108.8 no
C12 . C13 C14 . 112.2(2) yes
C12 . C13 H131 . 108.3 no
C14 . C13 H131 . 109.3 no
C12 . C13 H132 . 109.1 no
C14 . C13 H132 . 110.4 no
H131 . C13 H132 . 107.4 no
C13 . C14 O15 . 111.4(2) yes
C13 . C14 H141 . 109.1 no
O15 . C14 H141 . 109.3 no
C13 . C14 H142 . 109.8 no
O15 . C14 H142 . 106.7 no
H141 . C14 H142 . 110.6 no
C14 . O15 H151 . 112.7 no
C14 . O15 H152 . 108.9 no
H151 . O15 H152 . 127.4 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 1.7342(13) yes
S1 C2 . 1.7457(14) yes
C2 C3 . 1.4111(19) yes
C2 C8 . 1.3960(18) yes
C3 C4 . 1.4361(18) yes
C3 C5 . 1.394(2) yes
C4 C4 4_656 1.364(3) yes
C5 C6 . 1.378(2) yes
C5 H51 . 0.949 no
C6 C7 . 1.401(2) yes
C6 H61 . 0.957 no
C7 C8 . 1.385(2) yes
C7 C9 . 1.520(2) yes
C8 H81 . 0.934 no
C9 C10 . 1.520(2) yes
C9 H91 . 0.982 no
C9 H92 . 1.000 no
C10 C11 . 1.524(2) yes
C10 H101 . 0.993 no
C10 H102 . 0.980 no
C11 C12 . 1.514(3) yes
C11 H111 . 0.972 no
C11 H112 . 0.973 no
C12 C13 . 1.533(3) yes
C12 H121 . 0.993 no
C12 H122 . 0.978 no
C13 C14 . 1.500(3) yes
C13 H131 . 0.987 no
C13 H132 . 0.971 no
C14 O15 . 1.411(3) yes
C14 H141 . 0.998 no
C14 H142 . 0.982 no
O15 H151 . 0.784 no
O15 H152 . 0.780 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_766 170.33(11) 0.784 1.935 2.711(3) yes
O15 H152 O15 5_756 173.81(5) 0.780 1.923 2.700(3) yes
