#------------------------------------------------------------------------------
#$Date: 2020-06-25 01:18:52 +0300 (Thu, 25 Jun 2020) $
#$Revision: 253404 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/35/4003593.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_4003593
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            'C42 H28 F8 N2 O4'
_chemical_formula_weight         776.66
_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                66.7250(10)
_cell_angle_beta                 82.591(2)
_cell_angle_gamma                82.5310(10)
_cell_formula_units_Z            1
_cell_length_a                   4.4959(3)
_cell_length_b                   13.0881(9)
_cell_length_c                   15.9017(11)
_cell_measurement_temperature    100(2)
_cell_volume                     849.16(10)
_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  'Buker 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  0.0241
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21675
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.453
_diffrn_reflns_theta_min         2.799
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       prism
_exptl_crystal_F_000             398
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   0.9630
_exptl_transmission_factor_min   0.8830
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         6095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0438
_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)+(0.0694P)²+0.1796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4686
_reflns_number_total             6095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm0c01676_si_003.cif
_cod_data_source_block           SS051116_0m_a
_cod_database_code               4003593
_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   0.883
_shelx_estimated_absorpt_t_max   0.963
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 0.33733(15) 0.24387(6) 0.13118(5) 0.02367(15) Uani 1 1 d . . . . .
F002 F 1.11858(15) -0.02292(6) 0.10426(5) 0.02367(15) Uani 1 1 d . . . . .
F003 F 1.32953(15) 0.12768(7) -0.05598(5) 0.02960(17) Uani 1 1 d . . . . .
F004 F 0.5625(2) 0.39545(6) -0.02445(5) 0.03334(18) Uani 1 1 d . . . . .
O005 O 0.78459(17) -0.00588(6) 0.28604(5) 0.01713(15) Uani 1 1 d . . . . .
O006 O 0.5227(2) 0.13895(7) 0.31054(6) 0.0280(2) Uani 1 1 d . . . . .
C007 C 0.9192(2) 0.06928(8) 0.55108(6) 0.01348(17) Uani 1 1 d . . . . .
C008 C 0.7068(2) 0.05982(8) 0.33354(6) 0.01522(17) Uani 1 1 d . . . . .
C009 C 0.8176(2) 0.14484(8) 0.59531(6) 0.01557(18) Uani 1 1 d . . . . .
C00A C 0.8688(2) 0.02427(8) 0.41807(6) 0.01349(17) Uani 1 1 d . . . . .
C00B C 0.7928(2) 0.09035(8) 0.46905(6) 0.01427(17) Uani 1 1 d . . . . .
H00B H 0.6486 0.1527 0.4474 0.017 Uiso 1 1 calc R U . . .
N00C N 0.1173(3) 0.56873(9) 0.71550(9) 0.0335(3) Uani 1 1 d . . . . .
C00D C 0.7240(2) 0.10514(8) 0.12379(7) 0.01541(17) Uani 1 1 d . . . . .
C00E C 0.5534(2) 0.30168(8) 0.65029(7) 0.01577(18) Uani 1 1 d . . . . .
C00F C 0.7014(2) 0.21532(8) 0.62310(7) 0.01649(18) Uani 1 1 d . . . . .
C00G C 0.9766(2) 0.08038(9) 0.07284(7) 0.01790(19) Uani 1 1 d . . . . .
C00H C 0.6034(2) 0.01610(9) 0.21053(7) 0.01729(18) Uani 1 1 d . . . . .
H00A H 0.3937 0.0400 0.2270 0.021 Uiso 1 1 calc R U . . .
H00C H 0.6011 -0.0535 0.2000 0.021 Uiso 1 1 calc R U . . .
C00I C 0.7030(3) 0.29168(9) 0.00655(8) 0.0224(2) Uani 1 1 d . . . . .
C00J C 1.0863(2) 0.15801(10) -0.00945(8) 0.0214(2) Uani 1 1 d . . . . .
C00K C 0.6093(3) 0.31450(9) 0.72980(7) 0.0208(2) Uani 1 1 d . . . . .
H00K H 0.7479 0.2623 0.7694 0.025 Uiso 1 1 calc R U . . .
C00L C 0.4663(3) 0.40187(9) 0.75184(7) 0.0216(2) Uani 1 1 d . . . . .
H00L H 0.5085 0.4087 0.8063 0.026 Uiso 1 1 calc R U . . .
C00M C 0.5887(2) 0.21357(9) 0.08821(7) 0.01770(19) Uani 1 1 d . . . . .
C00N C 0.2590(2) 0.48090(9) 0.69499(8) 0.0212(2) Uani 1 1 d . . . . .
C00O C 0.9509(3) 0.26515(10) -0.04403(8) 0.0241(2) Uani 1 1 d . . . . .
H00O H 1.0258 0.3189 -0.1007 0.029 Uiso 1 1 calc R U . . .
C00P C 0.3460(3) 0.37956(9) 0.59417(8) 0.0238(2) Uani 1 1 d . . . . .
H00P H 0.3028 0.3720 0.5401 0.029 Uiso 1 1 calc R U . . .
C00Q C 0.2030(3) 0.46688(10) 0.61544(9) 0.0284(2) Uani 1 1 d . . . . .
H00Q H 0.0639 0.5186 0.5757 0.034 Uiso 1 1 calc R U . . .
C00R C -0.0816(3) 0.65118(10) 0.65163(11) 0.0346(3) Uani 1 1 d . . . . .
H00D H 0.0278 0.6824 0.5909 0.052 Uiso 1 1 calc R U . . .
H00E H -0.1519 0.7111 0.6735 0.052 Uiso 1 1 calc R U . . .
H00F H -0.2548 0.6156 0.6474 0.052 Uiso 1 1 calc R U . . .
C00S C 0.1824(3) 0.58592(11) 0.79538(10) 0.0350(3) Uani 1 1 d . . . . .
H00G H 0.1242 0.5222 0.8510 0.052 Uiso 1 1 calc R U . . .
H00H H 0.0686 0.6544 0.7970 0.052 Uiso 1 1 calc R U . . .
H00I H 0.3983 0.5928 0.7923 0.052 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'
N N 0.0061 0.0033 '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
C008 O005 C00H 115.12(8) . . ?
C00B C007 C00A 117.26(8) . 2_756 ?
C00B C007 C009 116.21(8) . . ?
C00A C007 C009 126.54(9) 2_756 . ?
O006 C008 O005 123.24(9) . . ?
O006 C008 C00A 123.45(9) . . ?
O005 C008 C00A 113.30(8) . . ?
C00F C009 C007 170.34(10) . . ?
C00B C00A C007 119.74(8) . 2_756 ?
C00B C00A C008 114.79(8) . . ?
C007 C00A C008 125.46(8) 2_756 . ?
C00A C00B C007 123.00(9) . . ?
C00A C00B H00B 118.5 . . ?
C007 C00B H00B 118.5 . . ?
C00N N00C C00S 121.12(11) . . ?
C00N N00C C00R 119.38(11) . . ?
C00S N00C C00R 119.28(10) . . ?
C00G C00D C00M 116.41(9) . . ?
C00G C00D C00H 120.24(9) . . ?
C00M C00D C00H 123.31(9) . . ?
C00K C00E C00P 117.77(9) . . ?
C00K C00E C00F 123.30(9) . . ?
C00P C00E C00F 118.92(9) . . ?
C009 C00F C00E 176.04(10) . . ?
F002 C00G C00J 118.74(9) . . ?
F002 C00G C00D 119.07(9) . . ?
C00J C00G C00D 122.19(10) . . ?
O005 C00H C00D 111.48(8) . . ?
O005 C00H H00A 109.3 . . ?
C00D C00H H00A 109.3 . . ?
O005 C00H H00C 109.3 . . ?
C00D C00H H00C 109.3 . . ?
H00A C00H H00C 108.0 . . ?
F004 C00I C00O 119.83(10) . . ?
F004 C00I C00M 118.48(10) . . ?
C00O C00I C00M 121.68(10) . . ?
F003 C00J C00O 120.06(10) . . ?
F003 C00J C00G 119.00(10) . . ?
C00O C00J C00G 120.94(10) . . ?
C00L C00K C00E 121.12(10) . . ?
C00L C00K H00K 119.4 . . ?
C00E C00K H00K 119.4 . . ?
C00K C00L C00N 121.17(10) . . ?
C00K C00L H00L 119.4 . . ?
C00N C00L H00L 119.4 . . ?
F001 C00M C00I 118.30(9) . . ?
F001 C00M C00D 120.51(9) . . ?
C00I C00M C00D 121.16(9) . . ?
N00C C00N C00Q 120.88(11) . . ?
N00C C00N C00L 121.85(11) . . ?
C00Q C00N C00L 117.27(9) . . ?
C00J C00O C00I 117.60(10) . . ?
C00J C00O H00O 121.2 . . ?
C00I C00O H00O 121.2 . . ?
C00Q C00P C00E 121.53(10) . . ?
C00Q C00P H00P 119.2 . . ?
C00E C00P H00P 119.2 . . ?
C00P C00Q C00N 121.14(10) . . ?
C00P C00Q H00Q 119.4 . . ?
C00N C00Q H00Q 119.4 . . ?
N00C C00R H00D 109.5 . . ?
N00C C00R H00E 109.5 . . ?
H00D C00R H00E 109.5 . . ?
N00C C00R H00F 109.5 . . ?
H00D C00R H00F 109.5 . . ?
H00E C00R H00F 109.5 . . ?
N00C C00S H00G 109.5 . . ?
N00C C00S H00H 109.5 . . ?
H00G C00S H00H 109.5 . . ?
N00C C00S H00I 109.5 . . ?
H00G C00S H00I 109.5 . . ?
H00H C00S H00I 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 C00M 1.3416(12) . ?
F002 C00G 1.3449(12) . ?
F003 C00J 1.3459(12) . ?
F004 C00I 1.3471(13) . ?
O005 C008 1.3414(11) . ?
O005 C00H 1.4513(12) . ?
O006 C008 1.2032(12) . ?
C007 C00B 1.4023(13) . ?
C007 C00A 1.4109(13) 2_756 ?
C007 C009 1.4250(13) . ?
C008 C00A 1.4912(13) . ?
C009 C00F 1.2069(13) . ?
C00A C00B 1.3885(13) . ?
C00A C007 1.4109(13) 2_756 ?
C00B H00B 0.9500 . ?
N00C C00N 1.3732(13) . ?
N00C C00S 1.4452(18) . ?
N00C C00R 1.4536(18) . ?
C00D C00G 1.3877(14) . ?
C00D C00M 1.3907(14) . ?
C00D C00H 1.5019(14) . ?
C00E C00K 1.3964(14) . ?
C00E C00P 1.3979(14) . ?
C00E C00F 1.4225(13) . ?
C00G C00J 1.3787(16) . ?
C00H H00A 0.9900 . ?
C00H H00C 0.9900 . ?
C00I C00O 1.3780(16) . ?
C00I C00M 1.3823(15) . ?
C00J C00O 1.3763(17) . ?
C00K C00L 1.3826(14) . ?
C00K H00K 0.9500 . ?
C00L C00N 1.4082(16) . ?
C00L H00L 0.9500 . ?
C00N C00Q 1.4053(17) . ?
C00O H00O 0.9500 . ?
C00P C00Q 1.3755(15) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00R H00D 0.9800 . ?
C00R H00E 0.9800 . ?
C00R H00F 0.9800 . ?
C00S H00G 0.9800 . ?
C00S H00H 0.9800 . ?
C00S H00I 0.9800 . ?
