#------------------------------------------------------------------------------
#$Date: 2019-11-17 06:52:45 +0100 (dom 17 de nov de 2019) $
#$Revision: 228751 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/90/1549099.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_1549099
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                 93.146(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3546(5)
_cell_length_b                   5.6236(3)
_cell_length_c                   50.168(3)
_cell_measurement_reflns_used    2577
_cell_measurement_temperature    275
_cell_measurement_theta_max      27.7520
_cell_measurement_theta_min      2.4760
_cell_volume                     2353.5(2)
_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      275
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0143
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  31.00   1.00   12.50    --   13.31 -57.00  60.00   72
  2  ω    -23.00  54.00   1.00   12.50    --   13.31-100.00  30.00   77
  3  ω    -13.00  25.00   1.00   12.50    --  -14.02-100.00-150.00   38
  4  ω    -51.00  35.00   1.00   12.50    --   13.31 -77.00 -90.00   86
  5  ω     -4.00  84.00   1.00   12.50    --   13.31  38.00-150.00   88
;
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0640129000
_diffrn_orient_matrix_UB_12      -0.0786797000
_diffrn_orient_matrix_UB_13      -0.0035852000
_diffrn_orient_matrix_UB_21      -0.0550226000
_diffrn_orient_matrix_UB_22      0.0959341000
_diffrn_orient_matrix_UB_23      0.0002744000
_diffrn_orient_matrix_UB_31      0.0107589000
_diffrn_orient_matrix_UB_32      0.0226157000
_diffrn_orient_matrix_UB_33      -0.0136865000
_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     0.0309
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            8011
_diffrn_reflns_theta_full        25.226
_diffrn_reflns_theta_max         27.826
_diffrn_reflns_theta_min         1.626
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94362
_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    1.244
_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         0.17
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9597
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.0029092
_refine_ls_shift/su_mean         0.0000922
_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: 
 839. 0.123E+04 657. 182. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0603
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0575
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              62
_reflns_limit_l_min              0
_reflns_number_gt                2017
_reflns_number_total             2431
_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   0.0443
_oxford_refine_ls_scale          3.97(3)
_oxford_reflns_number_all        2431
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c8sc00159f2.cif
_cod_data_source_block           275K
_cod_depositor_comments
'Adding full bibliography for 1549094--1549104.cif.'
_cod_original_cell_volume        2353.50(12)
_cod_original_sg_symbol_H-M      'I 1 2/a 1 '
_cod_database_code               1549099
_cell_oxdiff_length_a            8.3485(6)
_cell_oxdiff_length_b            5.6242(4)
_cell_oxdiff_length_c            50.202(2)
_cell_oxdiff_angle_alpha         89.964(5)
_cell_oxdiff_angle_beta          93.197(5)
_cell_oxdiff_angle_gamma         90.009(6)
_cell_oxdiff_volume              2353.5(3)
_oxdiff_exptl_absorpt_empirical_full_min 0.947
_oxdiff_exptl_absorpt_empirical_full_max 1.074
_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 87.38
_montpellier_reflns_redundancy_maxres 3.19
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 0.85409(6) 0.54066(8) 0.731524(8) 0.0455 1.0000 Uani .
C2 C 0.75738(19) 0.3710(3) 0.70630(3) 0.0384 1.0000 Uani .
C3 C 0.68366(18) 0.1670(3) 0.71605(3) 0.0355 1.0000 Uani .
C4 C 0.70732(18) 0.1573(3) 0.74454(3) 0.0346 1.0000 Uani .
C5 C 0.5993(2) 0.0178(3) 0.69794(3) 0.0465 1.0000 Uani .
C6 C 0.5897(2) 0.0762(4) 0.67117(3) 0.0523 1.0000 Uani .
C7 C 0.6623(2) 0.2802(4) 0.66144(3) 0.0483 1.0000 Uani .
C8 C 0.7472(2) 0.4276(3) 0.67914(3) 0.0452 1.0000 Uani .
C9 C 0.6509(2) 0.3383(4) 0.63188(3) 0.0598 1.0000 Uani .
C10 C 0.7797(2) 0.2176(4) 0.61654(3) 0.0587 1.0000 Uani .
C11 C 0.7848(2) 0.3034(5) 0.58777(3) 0.0667 1.0000 Uani .
C12 C 0.9184(3) 0.1921(5) 0.57291(4) 0.0732 1.0000 Uani .
C13 C 0.9363(3) 0.3002(5) 0.54527(4) 0.0829 1.0000 Uani .
C14 C 1.0755(3) 0.2005(6) 0.53162(4) 0.0965 1.0000 Uani .
O15 O 1.0956(2) 0.3130(4) 0.50671(3) 0.1208 1.0000 Uani .
H51 H 0.5496 -0.1174 0.7040 0.0541 1.0000 Uiso R
H61 H 0.5332 -0.0244 0.6590 0.0629 1.0000 Uiso R
H81 H 0.7941 0.5653 0.6729 0.0533 1.0000 Uiso R
H91 H 0.6632 0.5090 0.6304 0.0707 1.0000 Uiso R
H92 H 0.5450 0.2907 0.6248 0.0713 1.0000 Uiso R
H101 H 0.8839 0.2485 0.6259 0.0699 1.0000 Uiso R
H102 H 0.7621 0.0472 0.6170 0.0696 1.0000 Uiso R
H111 H 0.7983 0.4719 0.5879 0.0782 1.0000 Uiso R
H112 H 0.6838 0.2638 0.5782 0.0782 1.0000 Uiso R
H121 H 1.0195 0.2165 0.5832 0.0864 1.0000 Uiso R
H122 H 0.9001 0.0233 0.5715 0.0861 1.0000 Uiso R
H131 H 0.9504 0.4716 0.5472 0.0974 1.0000 Uiso R
H132 H 0.8374 0.2721 0.5343 0.0972 1.0000 Uiso R
H141 H 1.1731 0.2286 0.5429 0.1125 1.0000 Uiso R
H142 H 1.0603 0.0301 0.5284 0.1121 1.0000 Uiso R
H151 H 1.0406 0.4254 0.5047 0.1440 0.5000 Uiso R
H152 H 1.1860 0.3061 0.5035 0.1440 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 1.79 5.3 81.24 0.015 99.6 99.63
1 1.79 1.39 4.8 53.80 0.022 100.0 99.81
2 1.39 1.22 4.2 36.83 0.026 100.0 99.88
3 1.22 1.10 3.5 25.97 0.031 100.0 99.91
4 1.10 1.02 3.0 16.36 0.044 100.0 99.93
5 1.02 0.95 2.9 12.51 0.058 100.0 99.94
6 0.95 0.90 2.6 9.62 0.072 100.0 99.95
7 0.90 0.86 2.6 6.81 0.100 100.0 99.95
8 0.86 0.83 1.9 5.96 0.091 95.4 99.42
9 0.83 0.76 1.2 3.74 0.134 42.4 87.38
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 . 90.48(7) yes
S1 . C2 C3 . 112.87(11) yes
S1 . C2 C8 . 125.66(14) yes
C3 . C2 C8 . 121.45(16) yes
C2 . C3 C4 . 109.87(14) yes
C2 . C3 C5 . 118.66(14) yes
C4 . C3 C5 . 131.43(15) yes
C3 . C4 S1 4_656 133.22(12) yes
C3 . C4 C4 4_656 114.35(17) yes
S1 4_656 C4 C4 4_656 112.41(15) yes
C3 . C5 C6 . 119.30(17) yes
C3 . C5 H51 . 119.9 no
C6 . C5 H51 . 120.8 no
C5 . C6 C7 . 122.11(17) yes
C5 . C6 H61 . 119.1 no
C7 . C6 H61 . 118.8 no
C6 . C7 C8 . 119.02(15) yes
C6 . C7 C9 . 120.87(18) yes
C8 . C7 C9 . 120.11(18) yes
C2 . C8 C7 . 119.44(17) yes
C2 . C8 H81 . 120.8 no
C7 . C8 H81 . 119.7 no
C7 . C9 C10 . 113.03(16) yes
C7 . C9 H91 . 106.6 no
C10 . C9 H91 . 108.9 no
C7 . C9 H92 . 107.9 no
C10 . C9 H92 . 110.3 no
H91 . C9 H92 . 110.1 no
C9 . C10 C11 . 113.30(17) yes
C9 . C10 H101 . 108.2 no
C11 . C10 H101 . 109.2 no
C9 . C10 H102 . 108.6 no
C11 . C10 H102 . 110.2 no
H101 . C10 H102 . 107.2 no
C10 . C11 C12 . 113.28(18) yes
C10 . C11 H111 . 108.5 no
C12 . C11 H111 . 108.9 no
C10 . C11 H112 . 109.0 no
C12 . C11 H112 . 107.8 no
H111 . C11 H112 . 109.3 no
C11 . C12 C13 . 113.2(2) yes
C11 . C12 H121 . 108.8 no
C13 . C12 H121 . 107.4 no
C11 . C12 H122 . 109.1 no
C13 . C12 H122 . 110.3 no
H121 . C12 H122 . 107.9 no
C12 . C13 C14 . 112.6(2) yes
C12 . C13 H131 . 108.6 no
C14 . C13 H131 . 109.0 no
C12 . C13 H132 . 109.0 no
C14 . C13 H132 . 109.6 no
H131 . C13 H132 . 107.9 no
C13 . C14 O15 . 111.7(2) yes
C13 . C14 H141 . 108.6 no
O15 . C14 H141 . 107.6 no
C13 . C14 H142 . 110.3 no
O15 . C14 H142 . 108.2 no
H141 . C14 H142 . 110.5 no
C14 . O15 H151 . 111.9 no
C14 . O15 H152 . 108.9 no
H151 . O15 H152 . 125.4 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 1.7354(15) yes
S1 C2 . 1.7469(17) yes
C2 C3 . 1.403(2) yes
C2 C8 . 1.397(2) yes
C3 C4 . 1.433(2) yes
C3 C5 . 1.398(2) yes
C4 C4 4_656 1.362(3) yes
C5 C6 . 1.381(2) yes
C5 H51 . 0.926 no
C6 C7 . 1.398(3) yes
C6 H61 . 0.939 no
C7 C8 . 1.382(2) yes
C7 C9 . 1.516(2) yes
C8 H81 . 0.929 no
C9 C10 . 1.517(2) yes
C9 H91 . 0.969 no
C9 H92 . 0.973 no
C10 C11 . 1.525(2) yes
C10 H101 . 0.982 no
C10 H102 . 0.969 no
C11 C12 . 1.512(3) yes
C11 H111 . 0.954 no
C11 H112 . 0.974 no
C12 C13 . 1.529(3) yes
C12 H121 . 0.975 no
C12 H122 . 0.963 no
C13 C14 . 1.491(3) yes
C13 H131 . 0.975 no
C13 H132 . 0.982 no
C14 O15 . 1.419(3) yes
C14 H141 . 0.980 no
C14 H142 . 0.979 no
O15 H151 . 0.785 no
O15 H152 . 0.782 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_766 169.81(10) 0.785 1.928 2.704(3) yes
O15 H152 O15 5_756 174.78(7) 0.782 1.922 2.701(3) yes
