#------------------------------------------------------------------------------
#$Date: 2020-06-25 01:19:33 +0300 (Thu, 25 Jun 2020) $
#$Revision: 253406 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/35/4003595.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_4003595
loop_
_publ_author_name
'Sharber, Seth A.'
'Thomas, Samuel W.'
_publ_section_title
;
 Side Chain Regioisomers that Dictate Optical Properties and
 Mechanofluorochromism through Crystal Packing
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.0c01676
_journal_year                    2020
_chemical_formula_sum            'C40 H20 F8 O6'
_chemical_formula_weight         748.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.762(2)
_cell_angle_beta                 90.770(2)
_cell_angle_gamma                109.465(2)
_cell_formula_units_Z            1
_cell_length_a                   6.8850(7)
_cell_length_b                   7.0203(7)
_cell_length_c                   17.4630(18)
_cell_measurement_temperature    100(2)
_cell_volume                     795.61(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            28316
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         40.291
_diffrn_reflns_theta_min         3.078
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.9870
_exptl_transmission_factor_min   0.9600
_refine_diff_density_max         3.234
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         9950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1577
_refine_ls_R_factor_gt           0.1257
_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)+(0.1507P)²+2.1798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3429
_refine_ls_wR_factor_ref         0.3659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7107
_reflns_number_total             9950
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm0c01676_si_011.cif
_cod_data_source_block           020816_2345F3_OMe_0m_a
_cod_database_code               4003595
_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.
;
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.0685(3) 0.6963(2) 0.69386(10) 0.0271(3) Uani 1 1 d . . . . .
F002 F 0.2102(3) 1.1555(3) 0.90238(10) 0.0344(4) Uani 1 1 d . . . . .
F003 F 0.2867(3) 1.4675(3) 0.80466(12) 0.0351(4) Uani 1 1 d . . . . .
F004 F 0.1008(4) 0.7717(3) 0.84655(11) 0.0358(4) Uani 1 1 d . . . . .
O005 O 0.2990(3) 0.8962(3) 0.56792(10) 0.0196(3) Uani 1 1 d . . . . .
O006 O 0.1071(3) 0.7366(4) 0.46658(12) 0.0296(5) Uani 1 1 d . . . . .
C007 C 0.4644(3) 0.3669(3) 0.43497(11) 0.0126(3) Uani 1 1 d . . . . .
C008 C 0.1684(3) 1.0456(3) 0.66907(12) 0.0153(3) Uani 1 1 d . . . . .
C009 C 0.2491(3) 0.7594(3) 0.51122(12) 0.0146(3) Uani 1 1 d . . . . .
C00A C 0.3863(3) 0.6326(3) 0.50829(11) 0.0124(3) Uani 1 1 d . . . . .
C00B C 0.3538(3) 0.5009(3) 0.44559(11) 0.0129(3) Uani 1 1 d . . . . .
H00B H 0.2523 0.5014 0.4083 0.016 Uiso 1 1 calc R U . . .
C00C C 0.3761(3) 0.1421(3) 0.30892(12) 0.0169(3) Uani 1 1 d . . . . .
C00D C 0.4187(3) 0.2418(3) 0.36758(12) 0.0149(3) Uani 1 1 d . . . . .
C00E C 0.1272(3) 0.8883(3) 0.71995(13) 0.0180(3) Uani 1 1 d . . . . .
C00F C 0.3366(3) 0.0057(4) 0.24490(13) 0.0195(4) Uani 1 1 d . . . . .
O00G O 0.2531(5) -0.4280(4) 0.07120(15) 0.0467(7) Uani 1 1 d . . . . .
C00H C 0.1962(4) 1.1207(4) 0.82658(14) 0.0225(4) Uani 1 1 d . . . . .
C00I C 0.2209(3) 1.2428(3) 0.69774(13) 0.0188(3) Uani 1 1 d . . . . .
H00I H 0.2476 1.3527 0.6637 0.023 Uiso 1 1 calc R U . . .
C00J C 0.1420(4) 0.9241(4) 0.79825(14) 0.0214(4) Uani 1 1 d . . . . .
C00K C 0.1531(3) 1.0000(4) 0.58438(12) 0.0178(3) Uani 1 1 d . . . . .
H00A H 0.0115 0.9131 0.5698 0.021 Uiso 1 1 calc R U . . .
H00C H 0.1873 1.1267 0.5553 0.021 Uiso 1 1 calc R U . . .
C00L C 0.2338(4) 1.2777(4) 0.77634(15) 0.0223(4) Uani 1 1 d . . . . .
C00M C 0.3449(4) 0.0678(5) 0.17011(15) 0.0294(5) Uani 1 1 d . . . . .
H00M H 0.3710 0.2061 0.1590 0.035 Uiso 1 1 calc R U . . .
C00N C 0.2935(4) -0.2034(4) 0.25946(17) 0.0268(5) Uani 1 1 d . . . . .
H00N H 0.2840 -0.2470 0.3110 0.032 Uiso 1 1 calc R U . . .
C00O C 0.2770(5) -0.2797(5) 0.12577(17) 0.0302(5) Uani 1 1 d . . . . .
C00P C 0.3143(5) -0.0767(5) 0.11010(16) 0.0317(6) Uani 1 1 d . . . . .
H00P H 0.3192 -0.0349 0.0584 0.038 Uiso 1 1 calc R U . . .
C00Q C 0.2653(5) -0.3441(5) 0.20098(17) 0.0296(5) Uani 1 1 d . . . . .
H00Q H 0.2384 -0.4827 0.2119 0.036 Uiso 1 1 calc R U . . .
C00R C 0.2655(12) -0.3704(9) -0.0060(2) 0.078(2) Uani 1 1 d . . . . .
H00D H 0.1591 -0.3103 -0.0174 0.116 Uiso 1 1 calc R U . . .
H00E H 0.2445 -0.4896 -0.0391 0.116 Uiso 1 1 calc R U . . .
H00F H 0.4017 -0.2713 -0.0151 0.116 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
_geom_angle_publ_flag
C009 O005 C00K 116.95(16) . . ?
C00B C007 C00A 117.56(16) . 2_666 ?
C00B C007 C00D 117.43(16) . . ?
C00A C007 C00D 125.01(16) 2_666 . ?
C00E C008 C00I 119.0(2) . . ?
C00E C008 C00K 119.41(19) . . ?
C00I C008 C00K 121.6(2) . . ?
O006 C009 O005 124.15(18) . . ?
O006 C009 C00A 122.77(19) . . ?
O005 C009 C00A 113.07(16) . . ?
C00B C00A C007 119.52(16) . 2_666 ?
C00B C00A C009 115.35(16) . . ?
C007 C00A C009 125.07(16) 2_666 . ?
C00A C00B C007 122.91(17) . . ?
C00A C00B H00B 118.5 . . ?
C007 C00B H00B 118.5 . . ?
C00D C00C C00F 172.2(2) . . ?
C00C C00D C007 177.0(2) . . ?
F001 C00E C00J 118.6(2) . . ?
F001 C00E C008 120.2(2) . . ?
C00J C00E C008 121.2(2) . . ?
C00M C00F C00N 118.9(2) . . ?
C00M C00F C00C 123.1(2) . . ?
C00N C00F C00C 118.0(2) . . ?
C00O O00G C00R 117.4(4) . . ?
F002 C00H C00L 120.8(2) . . ?
F002 C00H C00J 119.7(3) . . ?
C00L C00H C00J 119.5(2) . . ?
C00L C00I C008 119.5(2) . . ?
C00L C00I H00I 120.2 . . ?
C008 C00I H00I 120.2 . . ?
F004 C00J C00E 120.6(2) . . ?
F004 C00J C00H 119.7(2) . . ?
C00E C00J C00H 119.7(2) . . ?
O005 C00K C008 106.98(16) . . ?
O005 C00K H00A 110.3 . . ?
C008 C00K H00A 110.3 . . ?
O005 C00K H00C 110.3 . . ?
C008 C00K H00C 110.3 . . ?
H00A C00K H00C 108.6 . . ?
F003 C00L C00H 118.8(2) . . ?
F003 C00L C00I 120.1(2) . . ?
C00H C00L C00I 121.1(2) . . ?
C00F C00M C00P 119.2(3) . . ?
C00F C00M H00M 120.4 . . ?
C00P C00M H00M 120.4 . . ?
C00Q C00N C00F 121.9(3) . . ?
C00Q C00N H00N 119.1 . . ?
C00F C00N H00N 119.1 . . ?
O00G C00O C00Q 115.1(3) . . ?
O00G C00O C00P 124.5(3) . . ?
C00Q C00O C00P 120.4(3) . . ?
C00O C00P C00M 120.8(3) . . ?
C00O C00P H00P 119.6 . . ?
C00M C00P H00P 119.6 . . ?
C00N C00Q C00O 118.8(3) . . ?
C00N C00Q H00Q 120.6 . . ?
C00O C00Q H00Q 120.6 . . ?
O00G C00R H00D 109.5 . . ?
O00G C00R H00E 109.5 . . ?
H00D C00R H00E 109.5 . . ?
O00G C00R H00F 109.5 . . ?
H00D C00R H00F 109.5 . . ?
H00E C00R H00F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00E 1.343(3) . ?
F002 C00H 1.339(3) . ?
F003 C00L 1.345(3) . ?
F004 C00J 1.329(3) . ?
O005 C009 1.329(3) . ?
O005 C00K 1.453(2) . ?
O006 C009 1.209(3) . ?
C007 C00B 1.405(2) . ?
C007 C00A 1.417(3) 2_666 ?
C007 C00D 1.426(3) . ?
C008 C00E 1.384(3) . ?
C008 C00I 1.393(3) . ?
C008 C00K 1.504(3) . ?
C009 C00A 1.500(2) . ?
C00A C00B 1.390(3) . ?
C00A C007 1.417(3) 2_666 ?
C00B H00B 0.9500 . ?
C00C C00D 1.209(3) . ?
C00C C00F 1.425(3) . ?
C00E C00J 1.383(3) . ?
C00F C00M 1.378(4) . ?
C00F C00N 1.424(4) . ?
O00G C00O 1.369(3) . ?
O00G C00R 1.407(6) . ?
C00H C00L 1.376(4) . ?
C00H C00J 1.387(4) . ?
C00I C00L 1.387(3) . ?
C00I H00I 0.9500 . ?
C00K H00A 0.9900 . ?
C00K H00C 0.9900 . ?
C00M C00P 1.412(4) . ?
C00M H00M 0.9500 . ?
C00N C00Q 1.377(4) . ?
C00N H00N 0.9500 . ?
C00O C00Q 1.390(4) . ?
C00O C00P 1.393(5) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00R H00D 0.9800 . ?
C00R H00E 0.9800 . ?
C00R H00F 0.9800 . ?
