#------------------------------------------------------------------------------
#$Date: 2019-11-24 11:17:01 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237768 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/75/7237551.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_7237551
loop_
_publ_author_name
'Mullin, William J.'
'Pawle, Robert H.'
'Sharber, Seth A.'
'Müller, Peter'
'Thomas, Samuel W.'
_publ_section_title
;
 Programmed twisting of phenylene--ethynylene linkages from aromatic
 stacking interactions
;
_journal_issue                   5
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1198
_journal_paper_doi               10.1039/C8TC05612A
_journal_volume                  7
_journal_year                    2019
_chemical_formula_sum            'C40 H16 F10 O4 S2'
_chemical_formula_weight         814.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-24 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.92(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.738(18)
_cell_length_b                   5.738(6)
_cell_length_c                   16.944(16)
_cell_measurement_reflns_used    6646
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      23.18
_cell_measurement_theta_min      2.30
_cell_volume                     1721(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.830
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.830
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13709
_diffrn_reflns_point_group_measured_fraction_full 0.830
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        23.726
_diffrn_reflns_theta_max         23.726
_diffrn_reflns_theta_min         1.151
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       prism
_exptl_crystal_F_000             820
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.216
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0729
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1614P)²+1.3482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2434
_refine_ls_wR_factor_ref         0.2683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1760
_reflns_number_total             2174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc05612a2.cif
_cod_data_source_block           WM0189_1_0ma_a
_cod_original_cell_volume        1720(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7237551
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S0 S 0.93314(9) 0.2771(2) 0.43977(7) 0.0592(6) Uani 1 1 d . .
C1 C 0.8129(3) 0.6647(9) 0.1890(3) 0.0465(11) Uani 1 1 d . .
O1 O 0.7570(4) 0.7424(8) 0.3465(2) 0.0877(17) Uani 1 1 d . .
O2 O 0.7168(3) 1.0950(6) 0.3067(2) 0.0646(11) Uani 1 1 d . .
C2 C 0.7686(3) 0.8572(8) 0.2114(3) 0.0465(11) Uani 1 1 d . .
C3 C 0.7426(4) 1.0172(10) 0.1543(3) 0.0625(14) Uani 1 1 d . .
H3 H 0.7142 1.1446 0.1688 0.075 Uiso 1 1 calc R U
C4 C 0.7585(4) 0.9887(11) 0.0759(3) 0.0749(18) Uani 1 1 d . .
H4 H 0.7415 1.0986 0.0385 0.090 Uiso 1 1 calc R U
C5 C 0.7993(4) 0.7993(12) 0.0529(3) 0.0733(18) Uani 1 1 d . .
H5 H 0.8083 0.7795 -0.0001 0.088 Uiso 1 1 calc R U
C6 C 0.8272(3) 0.6372(11) 0.1087(3) 0.0625(14) Uani 1 1 d . .
H6 H 0.8553 0.5106 0.0929 0.075 Uiso 1 1 calc R U
C12 C 0.8475(3) 0.5010(9) 0.2444(3) 0.0503(12) Uani 1 1 d . .
C13 C 0.8811(3) 0.3623(9) 0.2861(3) 0.0534(13) Uani 1 1 d . .
C14 C 0.9209(3) 0.2080(8) 0.3402(3) 0.0498(12) Uani 1 1 d . .
C15 C 0.9541(3) -0.0017(9) 0.3248(3) 0.0573(13) Uani 1 1 d . .
H15 H 0.9534 -0.0673 0.2745 0.069 Uiso 1 1 calc R U
C16 C 0.9892(3) -0.1067(9) 0.3921(3) 0.0560(13) Uani 1 1 d . .
H16 H 1.0135 -0.2502 0.3910 0.067 Uiso 1 1 calc R U
C17 C 0.9845(3) 0.0222(8) 0.4604(3) 0.0488(12) Uani 1 1 d . .
C21 C 0.7483(3) 0.8856(9) 0.2953(3) 0.0512(12) Uani 1 1 d . .
C22 C 0.6905(4) 1.1454(11) 0.3844(3) 0.0663(15) Uani 1 1 d . .
H22A H 0.7019 1.3060 0.3986 0.080 Uiso 1 1 calc R U
H22B H 0.7161 1.0451 0.4238 0.080 Uiso 1 1 calc R U
C23 C 0.6064(3) 1.1049(9) 0.3824(2) 0.0541(13) Uani 1 1 d . .
C24 C 0.5733(4) 0.9117(9) 0.4167(3) 0.0593(15) Uani 1 1 d . .
F24 F 0.6164(3) 0.7529(6) 0.4564(2) 0.0859(13) Uani 1 1 d . .
C25 C 0.4963(4) 0.8759(9) 0.4124(3) 0.0622(15) Uani 1 1 d . .
F25 F 0.4663(3) 0.6879(6) 0.4471(2) 0.0899(14) Uani 1 1 d . .
C26 C 0.4484(4) 1.0355(10) 0.3733(3) 0.0628(15) Uani 1 1 d . .
F26 F 0.3736(2) 1.0035(7) 0.3703(2) 0.0888(12) Uani 1 1 d . .
C27 C 0.4793(4) 1.2300(9) 0.3394(3) 0.0572(14) Uani 1 1 d . .
F27 F 0.4334(2) 1.3856(6) 0.3005(2) 0.0822(11) Uani 1 1 d . .
C28 C 0.5564(4) 1.2606(8) 0.3442(3) 0.0549(14) Uani 1 1 d . .
F28 F 0.5844(2) 1.4515(6) 0.30906(18) 0.0744(10) Uani 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C14 S0 C17 91.9(2) . .
C6 C1 C2 118.9(4) . .
C6 C1 C12 117.5(5) . .
C2 C1 C12 123.6(4) . .
C21 O2 C22 118.0(4) . .
C3 C2 C1 119.4(4) . .
C3 C2 C21 119.9(5) . .
C1 C2 C21 120.7(4) . .
C4 C3 C2 120.6(5) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
C5 C4 C3 120.7(5) . .
C5 C4 H4 119.7 . .
C3 C4 H4 119.7 . .
C4 C5 C6 120.3(5) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C5 C6 C1 120.1(6) . .
C5 C6 H6 119.9 . .
C1 C6 H6 119.9 . .
C13 C12 C1 174.3(5) . .
C12 C13 C14 176.0(6) . .
C15 C14 C13 128.4(5) . .
C15 C14 S0 111.1(4) . .
C13 C14 S0 120.5(4) . .
C14 C15 C16 113.3(5) . .
C14 C15 H15 123.4 . .
C16 C15 H15 123.4 . .
C17 C16 C15 113.8(5) . .
C17 C16 H16 123.1 . .
C15 C16 H16 123.1 . .
C16 C17 C17 130.2(6) . 3_756
C16 C17 S0 110.0(4) . .
C17 C17 S0 119.8(5) 3_756 .
O1 C21 O2 122.9(4) . .
O1 C21 C2 125.8(5) . .
O2 C21 C2 111.3(4) . .
O2 C22 C23 109.1(5) . .
O2 C22 H22A 109.9 . .
C23 C22 H22A 109.9 . .
O2 C22 H22B 109.9 . .
C23 C22 H22B 109.9 . .
H22A C22 H22B 108.3 . .
C28 C23 C24 115.6(6) . .
C28 C23 C22 120.7(5) . .
C24 C23 C22 123.7(5) . .
F24 C24 C25 117.0(5) . .
F24 C24 C23 120.4(6) . .
C25 C24 C23 122.5(5) . .
F25 C25 C24 120.8(6) . .
F25 C25 C26 119.2(6) . .
C24 C25 C26 120.0(5) . .
F26 C26 C27 121.0(6) . .
F26 C26 C25 120.1(5) . .
C27 C26 C25 118.9(6) . .
F27 C27 C28 120.5(5) . .
F27 C27 C26 119.5(6) . .
C28 C27 C26 119.9(5) . .
F28 C28 C27 118.1(5) . .
F28 C28 C23 118.8(6) . .
C27 C28 C23 123.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S0 C14 1.732(5) .
S0 C17 1.746(5) .
C1 C6 1.410(7) .
C1 C2 1.423(7) .
C1 C12 1.436(7) .
O1 C21 1.197(6) .
O2 C21 1.344(7) .
O2 C22 1.455(6) .
C2 C3 1.390(7) .
C2 C21 1.499(6) .
C3 C4 1.386(8) .
C3 H3 0.9300 .
C4 C5 1.377(9) .
C4 H4 0.9300 .
C5 C6 1.392(9) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C12 C13 1.196(7) .
C13 C14 1.426(7) .
C14 C15 1.373(7) .
C15 C16 1.398(8) .
C15 H15 0.9300 .
C16 C17 1.381(7) .
C16 H16 0.9300 .
C17 C17 1.437(10) 3_756
C22 C23 1.509(9) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 C28 1.388(8) .
C23 C24 1.399(8) .
C24 F24 1.341(7) .
C24 C25 1.379(10) .
C25 F25 1.355(7) .
C25 C26 1.386(9) .
C26 F26 1.338(8) .
C26 C27 1.385(8) .
C27 F27 1.349(7) .
C27 C28 1.376(9) .
C28 F28 1.357(6) .
