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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/63/4126306.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_4126306
loop_
_publ_author_name
'Sharber, Seth A.'
'Baral, Rom Nath'
'Frausto, Fanny'
'Haas, Terry E.'
'Müller, Peter'
'Thomas Iii, Samuel W.'
_publ_section_title
;
 Substituent Effects That Control Conjugated Oligomer Conformation through
 Non-covalent Interactions.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b00878
_journal_year                    2017
_chemical_formula_sum            'C38 H14 F10 N2 O8'
_chemical_formula_weight         816.51
_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-2014/7
_audit_update_record
;
2016-11-15 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 102.455(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.1026(17)
_cell_length_b                   5.6463(7)
_cell_length_c                   17.9272(17)
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.49
_cell_measurement_theta_min      3.35
_cell_volume                     1591.6(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13599
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.761
_diffrn_reflns_theta_min         3.349
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       Needle
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   0.9930
_exptl_transmission_factor_min   0.4810
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0586
_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)+(0.1101P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2185
_reflns_number_total             2907
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b00878_si_012.cif
_cod_data_source_block           NO2-F5
_cod_database_code               4126306
_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   0.481
_shelx_estimated_absorpt_t_max   0.993
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 0.29776(9) 0.7288(3) 0.19983(8) 0.0354(4) Uani 1 1 d . .
F002 F 0.45805(10) 1.4335(3) 0.24660(9) 0.0360(4) Uani 1 1 d . .
F003 F 0.32921(10) 0.6427(3) 0.35035(8) 0.0359(4) Uani 1 1 d . .
F004 F 0.42371(10) 0.9495(3) 0.45003(8) 0.0400(4) Uani 1 1 d . .
F005 F 0.48798(10) 1.3478(3) 0.39670(9) 0.0426(5) Uani 1 1 d . .
O006 O 0.41625(11) 0.9405(3) 0.10806(9) 0.0292(4) Uani 1 1 d . .
O007 O 0.35644(12) 1.0238(4) -0.01451(10) 0.0357(5) Uani 1 1 d . .
O008 O 0.75937(13) -0.0886(4) 0.53844(10) 0.0423(5) Uani 1 1 d . .
O009 O 0.67263(13) -0.3824(4) 0.50463(11) 0.0456(6) Uani 1 1 d . .
N1 N 0.70746(14) -0.1993(5) 0.49084(12) 0.0338(6) Uani 1 1 d . .
C00B C 0.64561(15) 0.0681(5) 0.26629(13) 0.0264(5) Uani 1 1 d . .
C00C C 0.50270(15) 0.5669(5) 0.07368(13) 0.0271(5) Uani 1 1 d . .
H00C H 0.5047 0.6145 0.1249 0.033 Uiso 1 1 calc R U
C00D C 0.42455(15) 1.2373(5) 0.27016(14) 0.0285(6) Uani 1 1 d . .
C00E C 0.37648(15) 1.0833(5) 0.21797(13) 0.0259(5) Uani 1 1 d . .
C00F C 0.54901(15) 0.3699(5) 0.06153(13) 0.0262(5) Uani 1 1 d . .
C00G C 0.36003(15) 0.8386(5) 0.32458(14) 0.0284(6) Uani 1 1 d . .
C00H C 0.45321(14) 0.6994(5) 0.01485(13) 0.0260(5) Uani 1 1 d . .
C00I C 0.68618(15) -0.1056(5) 0.41228(13) 0.0281(6) Uani 1 1 d . .
C00J C 0.40315(15) 0.9035(5) 0.03236(13) 0.0280(6) Uani 1 1 d . .
C00K C 0.34457(15) 0.8851(5) 0.24731(14) 0.0276(5) Uani 1 1 d . .
C00L C 0.40815(15) 0.9954(5) 0.37507(13) 0.0300(6) Uani 1 1 d . .
C1 C 0.59355(15) 0.2463(5) 0.12821(13) 0.0286(6) Uani 1 1 d . .
C00N C 0.44073(15) 1.1952(5) 0.34860(14) 0.0317(6) Uani 1 1 d . .
C00O C 0.62032(15) 0.1659(5) 0.19074(14) 0.0287(6) Uani 1 1 d . .
C00P C 0.36273(16) 1.1189(5) 0.13273(13) 0.0283(6) Uani 1 1 d . .
H00A H 0.3022 1.0948 0.1077 0.034 Uiso 1 1 calc R U
H00B H 0.3801 1.2801 0.1207 0.034 Uiso 1 1 calc R U
C00Q C 0.70371(16) 0.1887(5) 0.32300(14) 0.0313(6) Uani 1 1 d . .
H00Q H 0.7289 0.3319 0.3110 0.038 Uiso 1 1 calc R U
C00R C 0.72435(16) 0.0991(5) 0.39644(14) 0.0321(6) Uani 1 1 d . .
H00R H 0.7643 0.1783 0.4352 0.038 Uiso 1 1 calc R U
C00S C 0.62890(16) -0.2302(6) 0.35810(14) 0.0330(6) Uani 1 1 d . .
H00S H 0.6041 -0.3733 0.3708 0.040 Uiso 1 1 calc R U
C00T C 0.60881(17) -0.1398(5) 0.28474(15) 0.0343(6) Uani 1 1 d . .
H00T H 0.5692 -0.2214 0.2464 0.041 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C00J O006 C00P 116.13(19) . .
O009 N1 O008 124.1(2) . .
O009 N1 C00I 118.2(2) . .
O008 N1 C00I 117.7(2) . .
C00T C00B C00Q 119.4(2) . .
C00T C00B C00O 120.1(2) . .
C00Q C00B C00O 120.4(2) . .
C00F C00C C00H 123.5(2) . .
C00F C00C H00C 118.2 . .
C00H C00C H00C 118.2 . .
F002 C00D C00E 120.7(2) . .
F002 C00D C00N 117.3(2) . .
C00E C00D C00N 122.0(2) . .
C00K C00E C00D 116.8(2) . .
C00K C00E C00P 120.5(2) . .
C00D C00E C00P 122.6(2) . .
C00C C00F C00H 118.2(2) . 3_665
C00C C00F C1 116.7(2) . .
C00H C00F C1 125.0(2) 3_665 .
F003 C00G C00K 120.3(2) . .
F003 C00G C00L 120.2(2) . .
C00K C00G C00L 119.4(2) . .
C00C C00H C00F 118.3(2) . 3_665
C00C C00H C00J 120.4(2) . .
C00F C00H C00J 121.3(2) 3_665 .
C00R C00I C00S 123.2(2) . .
C00R C00I N1 118.7(2) . .
C00S C00I N1 118.2(2) . .
O007 C00J O006 123.6(2) . .
O007 C00J C00H 125.2(2) . .
O006 C00J C00H 111.2(2) . .
F001 C00K C00G 117.9(2) . .
F001 C00K C00E 119.7(2) . .
C00G C00K C00E 122.4(2) . .
F004 C00L C00N 120.3(2) . .
F004 C00L C00G 119.4(2) . .
C00N C00L C00G 120.3(2) . .
C00O C1 C00F 167.4(3) . .
F005 C00N C00L 121.0(2) . .
F005 C00N C00D 119.9(2) . .
C00L C00N C00D 119.1(2) . .
C1 C00O C00B 175.5(3) . .
O006 C00P C00E 104.38(19) . .
O006 C00P H00A 110.9 . .
C00E C00P H00A 110.9 . .
O006 C00P H00B 110.9 . .
C00E C00P H00B 110.9 . .
H00A C00P H00B 108.9 . .
C00R C00Q C00B 119.9(3) . .
C00R C00Q H00Q 120.0 . .
C00B C00Q H00Q 120.0 . .
C00I C00R C00Q 118.7(2) . .
C00I C00R H00R 120.6 . .
C00Q C00R H00R 120.6 . .
C00I C00S C00T 117.7(3) . .
C00I C00S H00S 121.1 . .
C00T C00S H00S 121.1 . .
C00S C00T C00B 121.0(2) . .
C00S C00T H00T 119.5 . .
C00B C00T H00T 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F001 C00K 1.339(3) .
F002 C00D 1.340(3) .
F003 C00G 1.335(3) .
F004 C00L 1.338(3) .
F005 C00N 1.335(3) .
O006 C00J 1.344(3) .
O006 C00P 1.455(3) .
O007 C00J 1.209(3) .
O008 N1 1.229(3) .
O009 N1 1.226(3) .
N1 C00I 1.474(3) .
C00B C00T 1.387(4) .
C00B C00Q 1.401(4) .
C00B C00O 1.438(3) .
C00C C00F 1.382(4) .
C00C C00H 1.395(3) .
C00C H00C 0.9500 .
C00D C00E 1.385(4) .
C00D C00N 1.394(4) .
C00E C00K 1.382(4) .
C00E C00P 1.509(3) .
C00F C00H 1.417(3) 3_665
C00F C1 1.436(3) .
C00G C00K 1.379(4) .
C00G C00L 1.379(4) .
C00H C00F 1.417(3) 3_665
C00H C00J 1.478(4) .
C00I C00R 1.368(4) .
C00I C00S 1.379(4) .
C00L C00N 1.371(4) .
C1 C00O 1.200(4) .
C00P H00A 0.9900 .
C00P H00B 0.9900 .
C00Q C00R 1.382(4) .
C00Q H00Q 0.9500 .
C00R H00R 0.9500 .
C00S C00T 1.382(4) .
C00S H00S 0.9500 .
C00T H00T 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125510
