#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/72/1517243.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_1517243
loop_
_publ_author_name
'Pawle, R. H.'
'Haas, T. E.'
'Müller, P.'
'Thomas III, S. W.'
_publ_section_title
;
 Twisting and piezochromism of phenylene-ethynylenes with aromatic
 interactions between side chains and main chains
;
_journal_issue                   11
_journal_name_full               'Chem. Sci.'
_journal_page_first              4184
_journal_paper_doi               10.1039/C4SC01466A
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C38 H16 F10 O4'
_chemical_formula_weight         726.51
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 107.6540(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8870(7)
_cell_length_b                   31.518(3)
_cell_length_c                   7.1384(7)
_cell_measurement_temperature    100(2)
_cell_volume                     1476.5(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            22257
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.064
_exptl_absorpt_coefficient_mu    0.148
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.715
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.222
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0432
_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)+(0.0215P)²+1.8345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2814
_reflns_number_total             3013
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4sc01466a1.cif
_cod_data_source_block           rp_a
_cod_depositor_comments
'Adding full bibliography for 1517239--1517244.cif.'
_cod_original_cell_volume        1476.5(2)
_cod_database_code               1517243
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.902
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
F001 F 0.1889(2) 0.72496(4) 0.61723(18) 0.0272(3) Uani 1 1 d . U
F002 F 0.2435(2) 0.58674(4) 0.86664(17) 0.0265(3) Uani 1 1 d . U
F003 F 0.05512(19) 0.60942(4) 0.18309(16) 0.0249(3) Uani 1 1 d . U
F004 F 0.0800(2) 0.69402(4) 0.24510(18) 0.0299(3) Uani 1 1 d . U
F005 F 0.2705(2) 0.67090(4) 0.92753(17) 0.0282(3) Uani 1 1 d . U
O006 O 0.2896(2) 0.53926(4) 0.3824(2) 0.0202(3) Uani 1 1 d . U
O007 O 0.1114(3) 0.48207(5) 0.2453(2) 0.0326(4) Uani 1 1 d . U
C008 C 0.4607(3) 0.46548(6) -0.1334(3) 0.0137(4) Uani 1 1 d . U
C009 C 0.2473(3) 0.50683(6) 0.2580(3) 0.0160(4) Uani 1 1 d . U
C00A C 0.1116(3) 0.62411(6) 0.3683(3) 0.0172(4) Uani 1 1 d . U
C00B C 0.3860(3) 0.50469(6) 0.1316(3) 0.0139(4) Uani 1 1 d . U
C00C C 0.3496(3) 0.47131(6) -0.0008(3) 0.0143(4) Uani 1 1 d . U
H00C H 0.2450 0.4516 -0.0015 0.017 Uiso 1 1 calc R U
C00D C 0.1781(3) 0.68311(6) 0.5875(3) 0.0190(4) Uani 1 1 d . U
C00E C 0.4153(3) 0.42876(6) -0.2578(3) 0.0159(4) Uani 1 1 d . U
C00F C 0.2056(3) 0.61243(6) 0.7103(3) 0.0171(4) Uani 1 1 d . U
C00G C 0.2184(3) 0.65561(6) 0.7441(3) 0.0187(4) Uani 1 1 d . U
C00H C 0.3432(3) 0.36086(6) -0.4824(3) 0.0173(4) Uani 1 1 d . U
C00I C 0.1236(3) 0.66718(6) 0.3975(3) 0.0196(4) Uani 1 1 d . U
C00J C 0.1535(3) 0.59548(6) 0.5230(3) 0.0153(4) Uani 1 1 d . U
C00K C 0.3781(3) 0.39699(6) -0.3537(3) 0.0173(4) Uani 1 1 d . U
C00L C 0.1419(3) 0.54858(6) 0.4853(3) 0.0174(4) Uani 1 1 d . U
H00A H 0.1753 0.5327 0.6108 0.021 Uiso 1 1 calc R U
H00B H 0.0032 0.5405 0.4038 0.021 Uiso 1 1 calc R U
C00M C 0.2940(3) 0.36745(6) -0.6850(3) 0.0202(4) Uani 1 1 d . U
H00M H 0.2823 0.3955 -0.7360 0.024 Uiso 1 1 calc R U
C00N C 0.3600(3) 0.31947(6) -0.4087(3) 0.0208(4) Uani 1 1 d . U
H00N H 0.3938 0.3147 -0.2711 0.025 Uiso 1 1 calc R U
C00O C 0.3273(3) 0.28532(7) -0.5373(3) 0.0253(4) Uani 1 1 d . U
H00O H 0.3386 0.2572 -0.4877 0.030 Uiso 1 1 calc R U
C00P C 0.2622(3) 0.33301(7) -0.8114(3) 0.0252(4) Uani 1 1 d . U
H00P H 0.2294 0.3375 -0.9491 0.030 Uiso 1 1 calc R U
C00Q C 0.2782(3) 0.29222(7) -0.7379(3) 0.0256(5) Uani 1 1 d . U
H00Q H 0.2555 0.2687 -0.8253 0.031 Uiso 1 1 calc R U
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'
O O 0.0106 0.0060 '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'
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
C009 O006 C00L 116.66(14) . .
C00C C008 C00B 117.89(17) . 3_665
C00C C008 C00E 117.64(16) . .
C00B C008 C00E 124.43(17) 3_665 .
O007 C009 O006 123.96(17) . .
O007 C009 C00B 123.30(17) . .
O006 C009 C00B 112.73(16) . .
F003 C00A C00I 118.50(17) . .
F003 C00A C00J 119.22(17) . .
C00I C00A C00J 122.28(17) . .
C00C C00B C008 119.50(17) . 3_665
C00C C00B C009 115.33(16) . .
C008 C00B C009 125.12(16) 3_665 .
C00B C00C C008 122.61(17) . .
F001 C00D C00G 120.41(17) . .
F001 C00D C00I 119.92(18) . .
C00G C00D C00I 119.66(18) . .
C00K C00E C008 176.9(2) . .
F002 C00F C00G 117.69(17) . .
F002 C00F C00J 120.02(17) . .
C00G C00F C00J 122.28(18) . .
F005 C00G C00D 119.79(17) . .
F005 C00G C00F 120.65(18) . .
C00D C00G C00F 119.55(17) . .
C00M C00H C00N 119.63(18) . .
C00M C00H C00K 119.01(18) . .
C00N C00H C00K 121.36(18) . .
F004 C00I C00A 120.90(17) . .
F004 C00I C00D 119.56(17) . .
C00A C00I C00D 119.53(18) . .
C00F C00J C00A 116.69(17) . .
C00F C00J C00L 122.57(17) . .
C00A C00J C00L 120.74(17) . .
C00E C00K C00H 174.1(2) . .
O006 C00L C00J 106.40(14) . .
C00P C00M C00H 119.89(19) . .
C00O C00N C00H 119.77(19) . .
C00Q C00O C00N 120.1(2) . .
C00Q C00P C00M 120.2(2) . .
C00P C00Q C00O 120.38(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F001 C00D 1.334(2) .
F002 C00F 1.339(2) .
F003 C00A 1.342(2) .
F004 C00I 1.338(2) .
F005 C00G 1.338(2) .
O006 C009 1.328(2) .
O006 C00L 1.453(2) .
O007 C009 1.201(2) .
C008 C00C 1.398(3) .
C008 C00B 1.411(3) 3_665
C008 C00E 1.434(3) .
C009 C00B 1.501(3) .
C00A C00I 1.372(3) .
C00A C00J 1.387(3) .
C00B C00C 1.385(3) .
C00B C008 1.411(3) 3_665
C00D C00G 1.374(3) .
C00D C00I 1.387(3) .
C00E C00K 1.196(3) .
C00F C00G 1.380(3) .
C00F C00J 1.382(3) .
C00H C00M 1.397(3) .
C00H C00N 1.398(3) .
C00H C00K 1.437(3) .
C00J C00L 1.500(3) .
C00M C00P 1.386(3) .
C00N C00O 1.388(3) .
C00O C00Q 1.385(3) .
C00P C00Q 1.380(3) .
