#------------------------------------------------------------------------------
#$Date: 2020-06-25 01:18:33 +0300 (Thu, 25 Jun 2020) $
#$Revision: 253403 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/35/4003592.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_4003592
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            'C38 H18 F8 O4'
_chemical_formula_weight         690.52
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-05-10 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   40.925(4)
_cell_length_b                   40.925(4)
_cell_length_c                   4.6169(6)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      2.98
_cell_volume                     6696.7(13)
_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 0.998
_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  0.0591
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            27719
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.427
_diffrn_reflns_theta_max         24.427
_diffrn_reflns_theta_min         2.986
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       Rod
_exptl_crystal_F_000             3150
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.9870
_exptl_transmission_factor_min   0.8780
_refine_diff_density_max         2.128
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0467
_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)+(0.0855P)²+28.8447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2056
_reflns_number_total             2459
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm0c01676_si_002.cif
_cod_data_source_block           SS170508_0m_a
_cod_original_cell_volume        6696.8(16)
_cod_database_code               4003592
_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   0.878
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
C1 C 0.46921(8) 0.48825(8) 0.8238(6) 0.0181(6) Uani 1 1 d . . . . .
H1 H 0.4479 0.4801 0.7011 0.022 Uiso 1 1 calc R U . . .
C2 C 0.48891(8) 0.46915(8) 0.8144(6) 0.0176(6) Uani 1 1 d . . . . .
C3 C 0.47918(8) 0.51918(8) 1.0059(6) 0.0179(6) Uani 1 1 d . . . . .
C21 C 0.47412(8) 0.43700(8) 0.6046(6) 0.0183(6) Uani 1 1 d . . . . .
O21 O 0.44941(6) 0.43061(6) 0.4339(4) 0.0246(5) Uani 1 1 d . . . . .
C22 C 0.47879(8) 0.38569(8) 0.4174(6) 0.0211(7) Uani 1 1 d . . . . .
H22A H 0.4989 0.3791 0.3935 0.025 Uiso 1 1 calc R U . . .
H22B H 0.4747 0.3943 0.2274 0.025 Uiso 1 1 calc R U . . .
O22 O 0.49100(6) 0.41618(6) 0.6270(4) 0.0215(5) Uani 1 1 d . . . . .
C23 C 0.44298(8) 0.35132(8) 0.5128(6) 0.0174(6) Uani 1 1 d . . . . .
C24 C 0.40804(8) 0.34059(8) 0.3910(6) 0.0178(6) Uani 1 1 d . . . . .
F24 F 0.40536(5) 0.36030(5) 0.1685(3) 0.0224(4) Uani 1 1 d . . . . .
C25 C 0.37570(8) 0.30929(8) 0.4869(6) 0.0202(7) Uani 1 1 d . . . . .
F25 F 0.34283(5) 0.30047(5) 0.3590(4) 0.0271(5) Uani 1 1 d . . . . .
C26 C 0.37658(8) 0.28717(8) 0.7068(6) 0.0212(7) Uani 1 1 d . . . . .
H26 H 0.3542 0.2658 0.7741 0.025 Uiso 1 1 calc R U . . .
C27 C 0.41124(9) 0.29721(8) 0.8264(6) 0.0202(6) Uani 1 1 d . . . . .
F27 F 0.41352(5) 0.27637(5) 1.0439(4) 0.0268(5) Uani 1 1 d . . . . .
C28 C 0.44355(8) 0.32868(8) 0.7336(6) 0.0191(6) Uani 1 1 d . . . . .
F28 F 0.47662(5) 0.33812(5) 0.8650(4) 0.0251(4) Uani 1 1 d . . . . .
C31 C 0.45600(8) 0.53609(8) 0.9922(6) 0.0196(7) Uani 1 1 d . . . . .
C32 C 0.43395(8) 0.54692(8) 0.9549(6) 0.0228(7) Uani 1 1 d . . . . .
C33 C 0.40670(8) 0.55863(8) 0.9085(6) 0.0235(7) Uani 1 1 d . . . . .
C34 C 0.40886(10) 0.58944(10) 1.0522(8) 0.0340(8) Uani 1 1 d . . . . .
H34 H 0.4289 0.6035 1.1840 0.041 Uiso 1 1 calc R U . . .
C35 C 0.38166(12) 0.59958(12) 1.0025(8) 0.0440(10) Uani 1 1 d . . . . .
H35 H 0.3834 0.6209 1.0983 0.053 Uiso 1 1 calc R U . . .
C36 C 0.35210(11) 0.57880(11) 0.8145(8) 0.0409(9) Uani 1 1 d . . . . .
H36 H 0.3333 0.5856 0.7839 0.049 Uiso 1 1 calc R U . . .
C37 C 0.34987(10) 0.54850(11) 0.6728(9) 0.0404(9) Uani 1 1 d . . . . .
H37 H 0.3296 0.5344 0.5430 0.048 Uiso 1 1 calc R U . . .
C38 C 0.37694(10) 0.53821(10) 0.7169(8) 0.0328(8) Uani 1 1 d . . . . .
H38 H 0.3753 0.5172 0.6164 0.039 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'
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'
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
C2 C1 C3 122.9(3) . . ?
C2 C1 H1 118.5 . . ?
C3 C1 H1 118.5 . . ?
C1 C2 C3 119.6(3) . 10_667 ?
C1 C2 C21 115.2(3) . . ?
C3 C2 C21 125.2(3) 10_667 . ?
C1 C3 C2 117.5(3) . 10_667 ?
C1 C3 C31 116.6(3) . . ?
C2 C3 C31 126.0(3) 10_667 . ?
O21 C21 O22 123.8(3) . . ?
O21 C21 C2 122.8(3) . . ?
O22 C21 C2 113.5(2) . . ?
O22 C22 C23 111.3(2) . . ?
O22 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
O22 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C21 O22 C22 115.3(2) . . ?
C28 C23 C24 116.5(3) . . ?
C28 C23 C22 120.4(3) . . ?
C24 C23 C22 123.1(3) . . ?
F24 C24 C25 118.4(3) . . ?
F24 C24 C23 120.0(2) . . ?
C25 C24 C23 121.6(3) . . ?
F25 C25 C26 120.1(3) . . ?
F25 C25 C24 118.5(3) . . ?
C26 C25 C24 121.4(3) . . ?
C25 C26 C27 117.5(3) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
F27 C27 C28 119.1(3) . . ?
F27 C27 C26 119.7(3) . . ?
C28 C27 C26 121.2(3) . . ?
F28 C28 C27 119.0(3) . . ?
F28 C28 C23 119.2(3) . . ?
C27 C28 C23 121.7(3) . . ?
C32 C31 C3 171.7(3) . . ?
C31 C32 C33 178.2(3) . . ?
C34 C33 C38 119.2(3) . . ?
C34 C33 C32 121.7(3) . . ?
C38 C33 C32 119.1(3) . . ?
C35 C34 C33 119.8(3) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C36 C35 C34 120.4(4) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C37 C36 C35 120.0(3) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.4(4) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C33 120.2(3) . . ?
C37 C38 H38 119.9 . . ?
C33 C38 H38 119.9 . . ?
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
C1 C2 1.376(4) . ?
C1 C3 1.400(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.413(4) 10_667 ?
C2 C21 1.496(4) . ?
C3 C2 1.413(4) 10_667 ?
C3 C31 1.428(4) . ?
C21 O21 1.204(3) . ?
C21 O22 1.342(4) . ?
C22 O22 1.456(3) . ?
C22 C23 1.503(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.386(4) . ?
C23 C24 1.388(4) . ?
C24 F24 1.344(3) . ?
C24 C25 1.376(4) . ?
C25 F25 1.343(3) . ?
C25 C26 1.372(4) . ?
C26 C27 1.379(4) . ?
C26 H26 0.9500 . ?
C27 F27 1.351(3) . ?
C27 C28 1.374(4) . ?
C28 F28 1.352(3) . ?
C31 C32 1.200(4) . ?
C32 C33 1.433(4) . ?
C33 C34 1.388(5) . ?
C33 C38 1.395(5) . ?
C34 C35 1.388(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.364(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.383(5) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
loop_
_publcif_info_cif.paper_type
?
