#------------------------------------------------------------------------------
#$Date: 2020-06-25 01:20:44 +0300 (Thu, 25 Jun 2020) $
#$Revision: 253410 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/35/4003599.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_4003599
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      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
_audit_update_record
;
2017-05-05 # Formatted by publCIF

;
_cell_angle_alpha                101.159(2)
_cell_angle_beta                 96.904(2)
_cell_angle_gamma                95.288(2)
_cell_formula_units_Z            1
_cell_length_a                   7.7154(7)
_cell_length_b                   9.1759(8)
_cell_length_c                   11.2358(10)
_cell_measurement_reflns_used    9854
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.85
_cell_measurement_theta_min      3.04
_cell_volume                     769.29(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_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  0.0207
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28044
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         40.918
_diffrn_reflns_theta_min         3.041
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            Violet
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       Prism
_exptl_crystal_F_000             350
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          1.000
_exptl_crystal_size_min          0.500
_exptl_transmission_factor_max   0.9380
_exptl_transmission_factor_min   0.8820
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         9932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0709P)²+0.1618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8138
_reflns_number_total             9932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm0c01676_si_005.cif
_cod_data_source_block           SS170504_0m_a
_cod_database_code               4003599
_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   0.882
_shelx_estimated_absorpt_t_max   0.938
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
C1 C 0.83661(7) 0.54821(6) 0.51238(5) 0.01199(8) Uani 1 1 d . . . . .
H1 H 0.7245 0.5809 0.5206 0.014 Uiso 1 1 calc R U . . .
C2 C 0.84583(7) 0.40496(6) 0.44537(5) 0.01116(8) Uani 1 1 d . . . . .
C3 C 0.98843(7) 0.64557(6) 0.56807(5) 0.01115(8) Uani 1 1 d . . . . .
C21 C 0.67249(7) 0.31545(6) 0.39046(5) 0.01179(8) Uani 1 1 d . . . . .
O21 O 0.53608(6) 0.37089(5) 0.37860(5) 0.01766(9) Uani 1 1 d . . . . .
C22 C 0.51866(8) 0.08013(7) 0.29743(6) 0.01566(10) Uani 1 1 d . . . . .
H22A H 0.4635 0.1248 0.2310 0.019 Uiso 1 1 calc R U . . .
H22B H 0.4360 0.0757 0.3579 0.019 Uiso 1 1 calc R U . . .
O22 O 0.68323(6) 0.16959(5) 0.35614(5) 0.01517(8) Uani 1 1 d . . . . .
C23 C 0.56058(8) -0.07348(6) 0.24618(5) 0.01282(9) Uani 1 1 d . . . . .
C24 C 0.53387(9) -0.19342(7) 0.30325(6) 0.01561(10) Uani 1 1 d . . . . .
F24 F 0.47406(8) -0.16813(6) 0.41232(4) 0.02525(10) Uani 1 1 d . . . . .
C25 C 0.56364(10) -0.33825(7) 0.25437(7) 0.01977(11) Uani 1 1 d . . . . .
H25 H 0.5435 -0.4174 0.2963 0.024 Uiso 1 1 calc R U . . .
C26 C 0.62367(9) -0.36246(8) 0.14219(7) 0.02085(12) Uani 1 1 d . . . . .
F26 F 0.65526(8) -0.50064(6) 0.09059(6) 0.03367(14) Uani 1 1 d . . . . .
C27 C 0.65374(9) -0.24781(8) 0.08046(6) 0.01948(11) Uani 1 1 d . . . . .
F27 F 0.71033(8) -0.27376(8) -0.02904(5) 0.03232(13) Uani 1 1 d . . . . .
C28 C 0.62399(8) -0.10509(7) 0.13450(6) 0.01564(10) Uani 1 1 d . . . . .
F28 F 0.65757(7) 0.00629(6) 0.07575(5) 0.02532(10) Uani 1 1 d . . . . .
C31 C 0.96577(8) 0.78986(6) 0.63515(6) 0.01327(9) Uani 1 1 d . . . . .
C32 C 0.94292(8) 0.91258(6) 0.68935(6) 0.01385(9) Uani 1 1 d . . . . .
C33 C 0.92427(7) 1.06064(6) 0.75164(5) 0.01249(9) Uani 1 1 d . . . . .
C34 C 0.94900(10) 1.18080(7) 0.69266(6) 0.01801(11) Uani 1 1 d . . . . .
H34 H 0.9784 1.1639 0.6118 0.022 Uiso 1 1 calc R U . . .
C35 C 0.93038(11) 1.32491(7) 0.75286(7) 0.02096(12) Uani 1 1 d . . . . .
H35 H 0.9478 1.4064 0.7130 0.025 Uiso 1 1 calc R U . . .
C36 C 0.88644(10) 1.35028(7) 0.87101(7) 0.02025(12) Uani 1 1 d . . . . .
H36 H 0.8722 1.4486 0.9112 0.024 Uiso 1 1 calc R U . . .
C37 C 0.86327(10) 1.23135(8) 0.93033(6) 0.01965(11) Uani 1 1 d . . . . .
H37 H 0.8345 1.2489 1.0114 0.024 Uiso 1 1 calc R U . . .
C38 C 0.88225(9) 1.08680(7) 0.87108(6) 0.01605(10) Uani 1 1 d . . . . .
H38 H 0.8667 1.0059 0.9118 0.019 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 121.88(5) . . ?
C2 C1 H1 119.1 . . ?
C3 C1 H1 119.1 . . ?
C1 C2 C3 119.87(5) . 2_766 ?
C1 C2 C21 115.49(5) . . ?
C3 C2 C21 124.64(5) 2_766 . ?
C1 C3 C2 118.25(5) . 2_766 ?
C1 C3 C31 117.84(5) . . ?
C2 C3 C31 123.92(5) 2_766 . ?
O21 C21 O22 123.55(5) . . ?
O21 C21 C2 123.13(5) . . ?
O22 C21 C2 113.32(5) . . ?
O22 C22 C23 107.43(5) . . ?
O22 C22 H22A 110.2 . . ?
C23 C22 H22A 110.2 . . ?
O22 C22 H22B 110.2 . . ?
C23 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
C21 O22 C22 114.79(5) . . ?
C24 C23 C28 115.88(5) . . ?
C24 C23 C22 123.10(6) . . ?
C28 C23 C22 120.98(6) . . ?
F24 C24 C25 117.86(6) . . ?
F24 C24 C23 118.11(6) . . ?
C25 C24 C23 124.02(6) . . ?
C26 C25 C24 117.13(6) . . ?
C26 C25 H25 121.4 . . ?
C24 C25 H25 121.4 . . ?
F26 C26 C25 119.69(7) . . ?
F26 C26 C27 118.45(7) . . ?
C25 C26 C27 121.86(6) . . ?
F27 C27 C28 120.53(7) . . ?
F27 C27 C26 121.02(6) . . ?
C28 C27 C26 118.45(6) . . ?
F28 C28 C27 118.22(6) . . ?
F28 C28 C23 119.16(6) . . ?
C27 C28 C23 122.62(6) . . ?
C32 C31 C3 178.14(7) . . ?
C31 C32 C33 177.03(6) . . ?
C38 C33 C34 119.63(5) . . ?
C38 C33 C32 120.65(5) . . ?
C34 C33 C32 119.72(5) . . ?
C35 C34 C33 119.86(6) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C36 C35 C34 120.37(6) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.94(6) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C38 120.14(6) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C37 C38 C33 120.05(6) . . ?
C37 C38 H38 120.0 . . ?
C33 C38 H38 120.0 . . ?
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 1.3952(7) . ?
C1 C3 1.4058(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.4148(8) 2_766 ?
C2 C21 1.4990(8) . ?
C3 C2 1.4148(8) 2_766 ?
C3 C31 1.4282(7) . ?
C21 O21 1.2146(7) . ?
C21 O22 1.3324(7) . ?
C22 O22 1.4553(7) . ?
C22 C23 1.4959(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.3885(9) . ?
C23 C28 1.3896(9) . ?
C24 F24 1.3470(8) . ?
C24 C25 1.3872(9) . ?
C25 C26 1.3797(11) . ?
C25 H25 0.9500 . ?
C26 F26 1.3452(8) . ?
C26 C27 1.3848(11) . ?
C27 F27 1.3401(8) . ?
C27 C28 1.3848(9) . ?
C28 F28 1.3419(8) . ?
C31 C32 1.2112(8) . ?
C32 C33 1.4312(8) . ?
C33 C38 1.3993(9) . ?
C33 C34 1.4021(9) . ?
C34 C35 1.3925(9) . ?
C34 H34 0.9500 . ?
C35 C36 1.3909(11) . ?
C35 H35 0.9500 . ?
C36 C37 1.3933(11) . ?
C36 H36 0.9500 . ?
C37 C38 1.3933(9) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
loop_
_publcif_info_cif.paper_type
?
