#------------------------------------------------------------------------------
#$Date: 2019-11-02 08:26:11 +0200 (Sat, 02 Nov 2019) $
#$Revision: 221097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/79/4127939.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_4127939
loop_
_publ_author_name
'Weiland, Kevin J.'
'Brandl, Thomas'
'Atz, Kenneth'
'Prescimone, Alessandro'
'Häussinger, Daniel'
'Šolomek, Tomáš'
'Mayor, Marcel'
_publ_section_title
;
 Mechanical Stabilization of Helical Chirality in a Macrocyclic
 Oligothiophene.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2104
_journal_page_last               2110
_journal_paper_doi               10.1021/jacs.8b11797
_journal_volume                  141
_journal_year                    2019
_chemical_compound_source        'Kevin Weiland'
_chemical_formula_moiety         'C48 H52 O4 S4'
_chemical_formula_sum            'C48 H52 O4 S4'
_chemical_formula_weight         821.20
_chemical_melting_point          ?
_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_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-05-22
_audit_creation_method           CRYSTALS_ver_14.61_build_6949
_cell_angle_alpha                95.895(3)
_cell_angle_beta                 91.044(3)
_cell_angle_gamma                117.920(3)
_cell_formula_units_Z            1
_cell_length_a                   7.6438(6)
_cell_length_b                   7.7858(6)
_cell_length_c                   19.8762(16)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    123
_cell_measurement_theta_max      71
_cell_measurement_theta_min      5
_cell_volume                     1036.72(14)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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      123
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.058
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12231
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.616
_diffrn_reflns_theta_min         2.241
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.454
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_recrystallization_method
; 
DCM / EtOH
;
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.82
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0297
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.0008247
_refine_ls_shift/su_mean         0.0000447
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0587
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0586
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                3432
_reflns_number_total             3671
_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   0.0722
_oxford_refine_ls_scale          0.18399(9)
_oxford_reflns_number_all        3653
_oxford_structure_analysis_title 'KW_W6_123K_0m in P-1'
_cod_data_source_file            ja8b11797_si_002.cif
_cod_data_source_block           KW_W6_123K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1036.71(14)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4127939
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
S1 S 0.23908(5) 0.01633(5) 0.275302(14) 0.0209 1.0000 Uani .
C2 C 0.28119(18) 0.10096(18) 0.36122(6) 0.0168 1.0000 Uani .
C3 C 0.29715(18) -0.01712(18) 0.41226(6) 0.0165 1.0000 Uani .
C4 C 0.39665(18) -0.13012(18) 0.40434(6) 0.0166 1.0000 Uani .
C5 C 0.36725(18) -0.25969(18) 0.45130(6) 0.0167 1.0000 Uani .
C6 C 0.27768(19) -0.25419(18) 0.51177(6) 0.0171 1.0000 Uani .
C7 C 0.25803(19) -0.40433(18) 0.55617(6) 0.0172 1.0000 Uani .
O2 O 0.19910(16) -0.37696(14) 0.61733(5) 0.0259 1.0000 Uani .
C9 C 0.1789(3) -0.5191(2) 0.66202(7) 0.0355 1.0000 Uani .
O1 O 0.28758(14) -0.54094(13) 0.53856(5) 0.0235 1.0000 Uani .
C11 C 0.23083(17) -0.10020(18) 0.52848(6) 0.0152 1.0000 Uani .
C12 C 0.22146(18) -0.00139(18) 0.47488(6) 0.0165 1.0000 Uani .
C13 C 0.22592(19) -0.01140(18) 0.59972(6) 0.0177 1.0000 Uani .
C14 C 0.4343(2) 0.08546(19) 0.64150(6) 0.0194 1.0000 Uani .
C15 C 0.27079(19) 0.27056(19) 0.37272(6) 0.0196 1.0000 Uani .
C16 C 0.2336(2) 0.33751(19) 0.31323(6) 0.0206 1.0000 Uani .
C17 C 0.21299(19) 0.21484(19) 0.25529(6) 0.0195 1.0000 Uani .
C18 C 0.1625(2) 0.23413(19) 0.18647(7) 0.0218 1.0000 Uani .
S2 S -0.00872(5) 0.31747(5) 0.174811(16) 0.0278 1.0000 Uani .
C20 C 0.0132(3) 0.3083(2) 0.08886(7) 0.0340 1.0000 Uani .
C21 C 0.1419(2) 0.2422(2) 0.07026(7) 0.0303 1.0000 Uani .
C22 C 0.2311(2) 0.1985(2) 0.12561(7) 0.0248 1.0000 Uani .
C23 C 0.3793(2) 0.1236(2) 0.11611(7) 0.0268 1.0000 Uani .
C24 C 0.2827(2) -0.0915(2) 0.08614(7) 0.0303 1.0000 Uani .
C25 C 0.4309(3) -0.1695(2) 0.07336(7) 0.0313 1.0000 Uani .
C26 C 0.5092(2) -0.2099(2) 0.13737(7) 0.0309 1.0000 Uani .
C27 C 0.6666(3) -0.2749(3) 0.12354(8) 0.0391 1.0000 Uani .
C28 C 0.7288(3) -0.3368(3) 0.18584(9) 0.0446 1.0000 Uani .
H51 H 0.4110 -0.3537 0.4428 0.0230 1.0000 Uiso R
H92 H 0.1172 -0.4988 0.7017 0.0570 1.0000 Uiso R
H91 H 0.3054 -0.5054 0.6780 0.0569 1.0000 Uiso R
H93 H 0.0978 -0.6515 0.6404 0.0570 1.0000 Uiso R
H121 H 0.1639 0.0813 0.4818 0.0229 1.0000 Uiso R
H131 H 0.1319 -0.1179 0.6239 0.0258 1.0000 Uiso R
H132 H 0.1822 0.0868 0.5949 0.0256 1.0000 Uiso R
H142 H 0.4349 -0.0042 0.6720 0.0252 1.0000 Uiso R
H141 H 0.4539 0.2052 0.6697 0.0249 1.0000 Uiso R
H151 H 0.2847 0.3371 0.4174 0.0262 1.0000 Uiso R
H161 H 0.2241 0.4543 0.3135 0.0281 1.0000 Uiso R
H201 H -0.0560 0.3468 0.0591 0.0421 1.0000 Uiso R
H211 H 0.1709 0.2255 0.0246 0.0389 1.0000 Uiso R
H231 H 0.4502 0.1448 0.1601 0.0339 1.0000 Uiso R
H232 H 0.4740 0.1996 0.0842 0.0339 1.0000 Uiso R
H241 H 0.1911 -0.1722 0.1182 0.0398 1.0000 Uiso R
H242 H 0.2092 -0.1050 0.0433 0.0400 1.0000 Uiso R
H252 H 0.5410 -0.0759 0.0495 0.0424 1.0000 Uiso R
H251 H 0.3640 -0.2936 0.0431 0.0423 1.0000 Uiso R
H261 H 0.5683 -0.0903 0.1690 0.0420 1.0000 Uiso R
H262 H 0.4023 -0.3080 0.1596 0.0420 1.0000 Uiso R
H271 H 0.7813 -0.1667 0.1081 0.0513 1.0000 Uiso R
H272 H 0.6177 -0.3840 0.0874 0.0515 1.0000 Uiso R
H282 H 0.8285 -0.3792 0.1761 0.0841 1.0000 Uiso R
H281 H 0.7876 -0.2225 0.2200 0.0841 1.0000 Uiso R
H283 H 0.6149 -0.4425 0.2035 0.0837 1.0000 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 0.0181 0.0091 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 0.0492 0.0322 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 0.3331 0.5567 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_
_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
_geom_angle_publ_flag
C2 . S1 C17 92.52(6) yes
S1 . C2 C3 121.81(9) yes
S1 . C2 C15 110.27(9) yes
C3 . C2 C15 127.40(11) yes
C2 . C3 C4 124.70(11) yes
C2 . C3 C12 116.91(11) yes
C4 . C3 C12 118.17(11) yes
C14 2_656 C4 C3 123.13(11) yes
C14 2_656 C4 C5 118.23(11) yes
C3 . C4 C5 117.13(11) yes
C4 . C5 C6 122.69(12) yes
C4 . C5 H51 119.1 no
C6 . C5 H51 118.2 no
C5 . C6 C7 115.44(11) yes
C5 . C6 C11 118.64(11) yes
C7 . C6 C11 125.66(11) yes
C6 . C7 O2 113.61(11) yes
C6 . C7 O1 123.76(11) yes
O2 . C7 O1 122.60(11) yes
C7 . O2 C9 115.34(10) yes
O2 . C9 H92 108.9 no
O2 . C9 H91 112.6 no
H92 . C9 H91 106.3 no
O2 . C9 H93 111.6 no
H92 . C9 H93 108.5 no
H91 . C9 H93 108.7 no
C6 . C11 C12 115.88(11) yes
C6 . C11 C13 125.92(11) yes
C12 . C11 C13 117.27(11) yes
C3 . C12 C11 123.27(11) yes
C3 . C12 H121 118.8 no
C11 . C12 H121 117.9 no
C11 . C13 C14 112.71(10) yes
C11 . C13 H131 107.8 no
C14 . C13 H131 107.5 no
C11 . C13 H132 106.9 no
C14 . C13 H132 110.3 no
H131 . C13 H132 111.7 no
C4 2_656 C14 C13 111.92(10) yes
C4 2_656 C14 H142 108.5 no
C13 . C14 H142 109.0 no
C4 2_656 C14 H141 110.6 no
C13 . C14 H141 109.5 no
H142 . C14 H141 107.2 no
C2 . C15 C16 114.08(11) yes
C2 . C15 H151 122.6 no
C16 . C15 H151 123.3 no
C15 . C16 C17 112.86(12) yes
C15 . C16 H161 123.4 no
C17 . C16 H161 123.7 no
S1 . C17 C16 110.24(10) yes
S1 . C17 C18 122.70(10) yes
C16 . C17 C18 126.92(12) yes
C17 . C18 S2 118.13(10) yes
C17 . C18 C22 130.59(12) yes
S2 . C18 C22 111.28(10) yes
C18 . S2 C20 92.08(7) yes
S2 . C20 C21 111.40(10) yes
S2 . C20 H201 123.4 no
C21 . C20 H201 125.2 no
C20 . C21 C22 114.12(12) yes
C20 . C21 H211 123.2 no
C22 . C21 H211 122.7 no
C21 . C22 C18 111.11(12) yes
C21 . C22 C23 122.79(12) yes
C18 . C22 C23 126.10(12) yes
C22 . C23 C24 112.58(13) yes
C22 . C23 H231 108.0 no
C24 . C23 H231 111.1 no
C22 . C23 H232 108.4 no
C24 . C23 H232 107.4 no
H231 . C23 H232 109.3 no
C23 . C24 C25 113.72(13) yes
C23 . C24 H241 109.2 no
C25 . C24 H241 106.6 no
C23 . C24 H242 107.6 no
C25 . C24 H242 109.5 no
H241 . C24 H242 110.3 no
C24 . C25 C26 113.61(12) yes
C24 . C25 H252 108.8 no
C26 . C25 H252 110.9 no
C24 . C25 H251 108.4 no
C26 . C25 H251 107.4 no
H252 . C25 H251 107.5 no
C25 . C26 C27 112.31(12) yes
C25 . C26 H261 108.4 no
C27 . C26 H261 108.5 no
C25 . C26 H262 111.3 no
C27 . C26 H262 109.4 no
H261 . C26 H262 106.7 no
C26 . C27 C28 112.46(13) yes
C26 . C27 H271 108.3 no
C28 . C27 H271 109.8 no
C26 . C27 H272 110.6 no
C28 . C27 H272 108.3 no
H271 . C27 H272 107.3 no
C27 . C28 H282 111.5 no
C27 . C28 H281 107.0 no
H282 . C28 H281 108.3 no
C27 . C28 H283 111.3 no
H282 . C28 H283 109.1 no
H281 . C28 H283 109.5 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 C2 . 1.7334(12) yes
S1 C17 . 1.7317(12) yes
C2 C3 . 1.4769(17) yes
C2 C15 . 1.3561(19) yes
C3 C4 . 1.4070(18) yes
C3 C12 . 1.4002(17) yes
C4 C14 2_656 1.5195(18) yes
C4 C5 . 1.3885(18) yes
C5 C6 . 1.4009(18) yes
C5 H51 . 0.939 no
C6 C7 . 1.4900(18) yes
C6 C11 . 1.4144(18) yes
C7 O2 . 1.3352(16) yes
C7 O1 . 1.2067(16) yes
O2 C9 . 1.4438(16) yes
C9 H92 . 0.962 no
C9 H91 . 0.966 no
C9 H93 . 0.966 no
C11 C12 . 1.3961(17) yes
C11 C13 . 1.5196(17) yes
C12 H121 . 0.936 no
C13 C14 . 1.5790(18) yes
C13 H131 . 0.986 no
C13 H132 . 0.979 no
C14 H142 . 0.972 no
C14 H141 . 0.982 no
C15 C16 . 1.4158(17) yes
C15 H151 . 0.958 no
C16 C17 . 1.3746(19) yes
C16 H161 . 0.945 no
C17 C18 . 1.4562(18) yes
C18 S2 . 1.7326(13) yes
C18 C22 . 1.3804(19) yes
S2 C20 . 1.7170(15) yes
C20 C21 . 1.348(2) yes
C20 H201 . 0.945 no
C21 C22 . 1.434(2) yes
C21 H211 . 0.948 no
C22 C23 . 1.504(2) yes
C23 C24 . 1.525(2) yes
C23 H231 . 0.977 no
C23 H232 . 0.985 no
C24 C25 . 1.530(2) yes
C24 H241 . 0.989 no
C24 H242 . 0.980 no
C25 C26 . 1.5186(19) yes
C25 H252 . 0.988 no
C25 H251 . 0.981 no
C26 C27 . 1.527(2) yes
C26 H261 . 0.970 no
C26 H262 . 0.972 no
C27 C28 . 1.519(2) yes
C27 H271 . 0.972 no
C27 H272 . 0.972 no
C28 H282 . 0.978 no
C28 H281 . 0.972 no
C28 H283 . 0.979 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
C15 H151 O1 1_565 171 0.96 2.49 3.442(2) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
3 -6 9 x
-1 2 11 x
-3 6 2 x
-1 2 8 x
0 0 4 x
3 -6 5 x
1 -2 3 x
1 -2 12 x
2 -4 2 x
-1 2 10 x
0 0 9 x
0 -3 2 x
0 0 11 x
1 -2 2 x
-3 6 6 x
-1 2 6 x
2 -4 11 x
5 -3 9 x
-2 4 9 x
2 -4 13 x
-1 2 2 x
3 1 5 x
1 -2 16 x
-1 -2 13 x
-4 1 1 x
3 1 2 x
5 -3 6 x
-2 4 0 x
1 -2 14 x
-1 0 4 x
2 -4 4 x
1 -2 19 x
-5 -1 3 x
-5 -1 2 x
-6 1 9 x
3 -6 6 x
1 -2 1 x
6 2 5 x
